Performance information

• Platinum-Catalyzed Hydrative Dimerization of Alkynylsilanes to α,β-Unsaturated Ketones
  Kasumi Kikuchi-Igarashi; Yuki Tahara; Haruna Hirano; Chinatsu Ambe; Hidenori Kinoshita; Katsukiyo Miura
  Organic Letters, Volume：26, Number：27, First page：5689, Last page：5694, Jul. 2024, [Reviewed]
  American Chemical Society (ACS), English, Scientific journal
  DOI：https://doi.org/10.1021/acs.orglett.4c01735
  DOI ID：10.1021/acs.orglett.4c01735, ISSN：1523-7060, eISSN：1523-7052
• Synthesis of Dihydrobenzosiloles and Silacyclopentanes by Double Hydroalumination of Terminal Alkynes
  Ryusei Osawa; Kotaro Ogihara; Fumine Hamasaki; Hidenori Kinoshita; Katsukiyo Miura
  Synlett, Volume：36, Number：03, First page：284, Last page：288, May 2024, [Reviewed]
  Abstract
  
  We have developed an efficient method for the synthesis of 2,3-dihydro-1H-1-benzosiloles in 19% to 90% isolated yield from 1-hydrosilyl-2-ethynylbenzenes by using two equivalents of diisobutylaluminum hydride. The reaction mechanism involves regioselective double hydroalumination of the alkyne moiety followed by cyclization to a 2-alanyldihydrobenzosilole. A silacyclopentane (silolane) was also synthesized in 97% isolated yield from the corresponding 4-silylbut-1-yne under the same reaction conditions. Although the substrate-scope study was conducted on a 0.5-mmol scale, a gram-scale reaction of (2-ethynylphenyl)(diphenyl)silane under the optimized reaction conditions successfully afforded the desired product in 94% isolated yield without loss of reactivity.
  Georg Thieme Verlag KG, English, Scientific journal
  DOI：https://doi.org/10.1055/a-2330-0874
  DOI ID：10.1055/a-2330-0874, ISSN：0936-5214, eISSN：1437-2096
• Synthetic Route to Benzostannoles via Al−Li-dimetal Intermediate and Their Application to Dibenzofulvene Synthesis　　　　　　　　　　　　　　　
  R. Kurokawa, H. Kinoshita, K. Miura
  Advanced Synthesis & Catalysis, Volume：366, Number：7, First page：1523, Last page：1530, Feb. 2024, [Reviewed]
  English, Scientific journal
• Palladium-Catalyzed Synthesis of 3,6-Diaryl-1-silylfulvenes: A Promising Entry for Preparing 1,3,6-Triarylfulvenes Bearing Three Different Aryl Groups　　　　　　　　　　　　　　　
  Hayato Ohki; Hidenori Kinoshita; Katsukiyo Miura
  Organic Letters, Volume：25, Number：8, First page：1331, Last page：1335, Mar. 2023, [Reviewed]
  Scientific journal
  DOI：https://doi.org/10.1021/acs.orglett.3c00340
  DOI ID：10.1021/acs.orglett.3c00340, ORCID：129352471
• One-Pot Direct Synthesis of Siloles from 1-Bromo-2-silylethynylbenzenes or 1-Bromo-4-silyl-1,3-enynes.　　　　　　　　　　　　　　　
  Koyo Kazama; Rei Kurokawa; Kei Inoue; Hidenori Kinoshita; Katsukiyo Miura
  The Journal of organic chemistry, Volume：87, Number：15, First page：10416, Last page：10421, Aug. 2022, [Reviewed], ［International magazine］
  We propose one-pot synthesis of siloles from readily available starting materials. This methodology is practical for the preparation of multisubstituted siloles in good to excellent yields with complete regioselectivity. Sequential reactions, such as lithiation, silylation, and diisobutylaluminum-hydride-promoted cyclization, enable the preparation of the siloles. This transformation provides siloles through two efficient C-Si bond formations in one vessel.
  AMER CHEMICAL SOC, English, Scientific journal
  DOI：https://doi.org/10.1021/acs.joc.2c00847
  DOI ID：10.1021/acs.joc.2c00847, ISSN：0022-3263, eISSN：1520-6904, PubMed ID：35802630, Web of Science ID：WOS:000826704700001
• Regio- and stereoselective synthesis of bromoalkenes by homolytic hydrobromination of alkynes with hydrogen bromide　　　　　　　　　　　　　　　
  Wataru Kumaki; Hidenori Kinoshita; Katsukiyo Miura
  Tetrahedron, Volume：110, First page：132687, Mar. 2022, [Reviewed]
  Homolytic hydrobromination of terminal and internal alkynes with a commercially available solution of hydrogen bromide in acetic acid has been investigated for regio- and stereoselective synthesis of bromoalkenes. Under an aerobic atmosphere at room temperature, the reaction of ethynylarenes with a small excess of HBr efficiently gave (2-bromoethenyl)arenes with good to high E-selectivity. (Alk-1-ynyl)arenes, or internal alkynes bearing both phenyl and alkyl groups at the sp-carbons also underwent the air-initiated hydrobromination to exhibit high Z-selectivity under kinetic conditions using a half equivalent of HBr.
  PERGAMON-ELSEVIER SCIENCE LTD, English, Scientific journal
  DOI：https://doi.org/10.1016/j.tet.2022.132687
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  DOI ID：10.1016/j.tet.2022.132687, ISSN：0040-4020, eISSN：1464-5416, SCOPUS ID：85125436506, Web of Science ID：WOS:000777863500003
• Electrochemical Properties and Electrochromism of 6-Aryl-1,3-bis(trimethylsilyl)fulvenes and Their Derivatives.　　　　　　　　　　　　　　　
  Ryota Tatemura; Mikio Yasutake; Hidenori Kinoshita; Katsukiyo Miura
  The Journal of organic chemistry, Volume：87, Number：1, First page：172, Last page：183, Jan. 2022, [Reviewed], ［International magazine］
  In this study, we have disclosed intriguing electrochromic properties of 6-aryl-1,3-bissilylfulvenes. The electrolyte solutions (0.1 M n-Bu4NClO4 in acetonitrile or dichloromethane) of some 6-aryl-1,3-bissilylfulvenes showed notable color changes when superimposed negative voltages were applied to the solutions. Investigation of the substituents at position 6 revealed that the solution of 1,3-bissilyl-6-anthracenylfulvene exhibited chromic changes under both applied superimposed negative and positive voltages and exhibited a three-color electrochromism. Electrochromic properties of 1,6-diarylfulvenes derived from 6-aryl-1,3-bissilylfulvenes were also investigated. The aryl group at position 1 also contributed to the electrochromism of fulvenes.
  AMER CHEMICAL SOC, English, Scientific journal
  DOI：https://doi.org/10.1021/acs.joc.1c02133
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  DOI ID：10.1021/acs.joc.1c02133, ISSN：0022-3263, eISSN：1520-6904, PubMed ID：34913709, SCOPUS ID：85121901069, Web of Science ID：WOS:000759551400016
• Synthesis of Polysubstituted Germoles and Benzogermoles Using a Substoichiometric Amount of Diisobutylaluminum Hydride.　　　　　　　　　　　　　　　
  Ko Kojima; Seiya Uchida; Hidenori Kinoshita; Katsukiyo Miura
  Organic letters, Volume：23, Number：12, First page：4598, Last page：4602, Jun. 2021, ［International magazine］
  We developed a synthetic route to unsymmetrically polysubstituted germoles bearing different substituents from 1-hydrogermyl-4-silyl-1,3-enynes. The reaction proceeded with 0.5 equiv of diisobutylaluminum hydride. Various 2-silylgermoles including benzogermoles were obtained in good to excellent yields. 2-Germylbenzogermoles could be also successfully synthesized from 1-hydrogermyl-4-germyl-1,3-enynes under the same reaction conditions.
  English, Scientific journal
  DOI：https://doi.org/10.1021/acs.orglett.1c01314
  DOI ID：10.1021/acs.orglett.1c01314, PubMed ID：34061552
• Synthesis of Polysubstituted Germoles and Benzogermoles Using a Substoichiometric Amount of Diisobutylaluminum Hydride　　　　　　　　　　　　　　　
  Ko Kojima; Seiya Uchida; Hidenori Kinoshita; Katsukiyo Miura
  Organic Letters, Volume：23, Number：12, First page：4598, Last page：4602, Jun. 2021, [Reviewed]
  We developed a synthetic route to unsymmetrically polysubstituted germoles bearing different substituents from 1-hydrogermyl-4-silyl-1,3-enynes. The reaction proceeded with 0.5 equiv of diisobutylaluminum hydride. Various 2-silylgermoles including benzogermoles were obtained in good to excellent yields. 2-Germylbenzogermoles could be also successfully synthesized from 1-hydrogermyl-4-germyl-1,3-enynes under the same reaction conditions.
  American Chemical Society (ACS), Scientific journal
  DOI：https://doi.org/10.1021/acs.orglett.1c01314
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  DOI ID：10.1021/acs.orglett.1c01314, ISSN：1523-7060, eISSN：1523-7052, PubMed ID：34061552, SCOPUS ID：85108438077, Web of Science ID：WOS:000664333200019
• Cyclization of 1-ethynyl-2-alkenylbenzenes to naphthalenes using Et2AlCl and DIBAL-H　　　　　　　　　　　　　　　
  Yuma Nonoyama; Kazuki Yaguchi; Hidenori Kinoshita; Katsukiyo Miura
  Tetrahedron Letters, Volume：62, Jan. 2021
  A one-pot procedure has been developed for the synthesis of substituted naphthalenes from 1-ethynyl-2-alkenylbenzenes. The successive reaction of a variety of 1-ethynyl-2-alkenylbenzenes with BuLi, Et2AlCl, and diisobutylaluminum hydride (DIBAL-H) in one pot gives the corresponding substituted naphthalenes in excellent yields. β, β-Bisaluminated styrenes, which are generated in situ, undergo an intramolecular cyclization reaction to form aluminated naphthalenes. The naphthylaluminum intermediate can be trapped with methanol‑d4 to form the deuterated product, which provides some mechanistic insight. The corresponding iodinated naphthalenes are also obtained on quenching the naphthylaluminum with N-iodosuccinimide (NIS) and iodine.
  Scientific journal
  DOI：https://doi.org/10.1016/j.tetlet.2020.152682
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  DOI ID：10.1016/j.tetlet.2020.152682, ISSN：0040-4039, eISSN：1873-3581, SCOPUS ID：85097782886
• Cyclization of 1-ethynyl-2-alkenylbenzenes to naphthalenes using Et2AlCl and DIBAL-H　　　　　　　　　　　　　　　
  Yuma Nonoyama; Kazuki Yaguchi; Hidenori Kinoshita; Katsukiyo Miura
  TETRAHEDRON LETTERS, Volume：62, Number：5, First page：152682, Jan. 2021
  A one-pot procedure has been developed for the synthesis of substituted naphthalenes from 1-ethynyl-2-alkenylbenzenes. The successive reaction of a variety of 1-ethynyl-2-alkenylbenzenes with BuLi, Et2AlCl, and diisobutylaluminum hydride (DIBAL-H) in one pot gives the corresponding substituted naphthalenes in excellent yields. beta, beta-Bisaluminated styrenes, which are generated in situ, undergo an intramolecular cyclization reaction to form aluminated naphthalenes. The naphthylaluminum intermediate can be trapped with methanol d(4) to form the deuterated product, which provides some mechanistic insight. The corresponding iodinated naphthalenes are also obtained on quenching the naphthylaluminum with N-iodosuccinimide (NIS) and iodine. (C) 2020 Elsevier Ltd. All rights reserved.
  PERGAMON-ELSEVIER SCIENCE LTD, English, Scientific journal
  DOI：https://doi.org/10.1016/j.tetlet.2020.152682
  DOI ID：10.1016/j.tetlet.2020.152682, ISSN：0040-4039, eISSN：1873-3581, Web of Science ID：WOS:000603489100008
• Diisobutylaluminum Hydride Promoted Selectivity-Switchable Synthesis of Benzothiophene Oxides and Benzothiophenes via an Al-Li-Dimetalated Intermediate.　　　　　　　　　　　　　　　
  Seiya Uchida; Hidenori Kinoshita; Katsukiyo Miura
  Organic letters, Volume：22, Number：8, First page：3123, Last page：3127, Apr. 2020, ［International magazine］
  We developed an efficient and direct method for synthesis of benzothiophene oxides from 1-bromo-2-[2-(trimethylsilyl)ethynyl]benzenes and thionyl chloride as an easily accessible source of the sulfinyl group. Benzothiophenes were also synthesized selectively by simply increasing the amount of thionyl chloride. These methods achieved efficient syntheses of various benzothiophene oxides and benzothiophenes. The further modification of the benzothiophene oxides obtained was also demonstrated.
  English, Scientific journal
  DOI：https://doi.org/10.1021/acs.orglett.0c00884
  DOI ID：10.1021/acs.orglett.0c00884, PubMed ID：32239951
• Diisobutylaluminum Hydride Promoted Selectivity-Switchable Synthesis of Benzothiophene Oxides and Benzothiophenes via an Al-Li-Dimetalated Intermediate　　　　　　　　　　　　　　　
  Seiya Uchida; Hidenori Kinoshita; Katsukiyo Miura
  Organic Letters, Volume：22, Number：8, First page：3123, Last page：3127, Apr. 2020
  We developed an efficient and direct method for synthesis of benzothiophene oxides from 1-bromo-2-[2-(trimethylsilyl)ethynyl]benzenes and thionyl chloride as an easily accessible source of the sulfinyl group. Benzothiophenes were also synthesized selectively by simply increasing the amount of thionyl chloride. These methods achieved efficient syntheses of various benzothiophene oxides and benzothiophenes. The further modification of the benzothiophene oxides obtained was also demonstrated.
  Scientific journal
  DOI：https://doi.org/10.1021/acs.orglett.0c00884
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  DOI ID：10.1021/acs.orglett.0c00884, ISSN：1523-7060, eISSN：1523-7052, PubMed ID：32239951, SCOPUS ID：85082799009
• Diisobutylaluminum Hydride Promoted Selectivity-Switchable Synthesis of Benzothiophene Oxides and Benzothiophenes via an Al-Li-Dimetalated Intermediate　　　　　　　　　　　　　　　
  Seiya Uchida; Hidenori Kinoshita; Katsukiyo Miura
  ORGANIC LETTERS, Volume：22, Number：8, First page：3123, Last page：3127, Apr. 2020
  We developed an efficient and direct method for synthesis of benzothiophene oxides from 1-bromo-2-[2-(trimethylsilyl)ethynyl]benzenes and thionyl chloride as an easily accessible source of the sulfinyl group. Benzothiophenes were also synthesized selectively by simply increasing the amount of thionyl chloride. These methods achieved efficient syntheses of various benzothiophene oxides and benzothiophenes. The further modification of the benzothiophene oxides obtained was also demonstrated.
  AMER CHEMICAL SOC, English, Scientific journal
  DOI：https://doi.org/10.1021/acs.orglett.0c00884
  DOI ID：10.1021/acs.orglett.0c00884, ISSN：1523-7060, eISSN：1523-7052, Web of Science ID：WOS:000526894000052
• Indium(III)-catalyzed intramolecular addition of silyl enolates to alkynes　　　　　　　　　　　　　　　
  Hidenori Kinoshita; Kenta Negishi; Saya Fushimi; Katsukiyo Miura
  Tetrahedron Letters, Volume：60, Number：26, First page：1732, Last page：1735, Jun. 2019
  In the presence of water and a catalytic amount of InBr3, intramolecular trans-addition of silyl enolates derived from ketones and an aldehyde to alkynes proceeded smoothly to give 4 to 7-membered carbocycles bearing an acyl group. When carboxylic anhydrides were used as electrophiles instead of water, the cyclized products could be functionalized with an additional acyl group.
  Scientific journal
  DOI：https://doi.org/10.1016/j.tetlet.2019.05.055
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  DOI ID：10.1016/j.tetlet.2019.05.055, ISSN：0040-4039, eISSN：1873-3581, SCOPUS ID：85066404597
• Indium(III)-catalyzed intramolecular addition of silyl enolates to alkynes　　　　　　　　　　　　　　　
  Hidenori Kinoshita; Kenta Negishi; Saya Fushimi; Katsukiyo Miura
  TETRAHEDRON LETTERS, Volume：60, Number：26, First page：1732, Last page：1735, Jun. 2019
  In the presence of water and a catalytic amount of InBr3, intramolecular trans-addition of silyl enolates derived from ketones and an aldehyde to alkynes proceeded smoothly to give 4 to 7-membered carbocydes bearing an acyl group. When carboxylic anhydrides were used as electrophiles instead of water, the cyclized products could be functionalized with an additional acyl group. (C) 2019 Elsevier Ltd. All rights reserved.
  PERGAMON-ELSEVIER SCIENCE LTD, English, Scientific journal
  DOI：https://doi.org/10.1016/j.tetlet.2019.05.055
  DOI ID：10.1016/j.tetlet.2019.05.055, ISSN：0040-4039, Web of Science ID：WOS:000474499200011
• Palladium-Catalyzed Regio- and Stereoselective Synthesis of (E)-1,3-Bissilyl-6-arylfulvenes from Aryl Iodides and Silylacetylenes　　　　　　　　　　　　　　　
  Souta Suzuki; Hidenori Kinoshita; Katsukiyo Miura
  Organic Letters, Volume：21, Number：6, First page：1612, Last page：1616, Mar. 2019
  An efficient synthetic route to (E)-1,3-bissilyl-6-arylfulvenes has been developed. The reaction of aryl iodides with trimethylsilylacetylene in the presence of a catalytic amount of PdBr 2 gives 6-aryl-1,3-bis(trimethylsilyl)fulvenes in good to excellent yields with complete regio- and stereoselectivity. The reaction involves trimerization of trimethylsilylacetylene and cleavage of one silyl group. The silylated fulvenes obtained could be converted into halogenated fulvenes by site-selective halodesilylation. The halogenated fulvenes underwent the Stille coupling leading to the corresponding arylated fulvenes.
  Scientific journal
  DOI：https://doi.org/10.1021/acs.orglett.9b00144
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  DOI ID：10.1021/acs.orglett.9b00144, ISSN：1523-7060, eISSN：1523-7052, PubMed ID：30789738, SCOPUS ID：85062369069
• Palladium-Catalyzed Regio- and Stereoselective Synthesis of ( E)-1,3-Bissilyl-6-arylfulvenes from Aryl Iodides and Silylacetylenes.　　　　　　　　　　　　　　　
  Souta Suzuki; Hidenori Kinoshita; Katsukiyo Miura
  Organic letters, Volume：21, Number：6, First page：1612, Last page：1616, Mar. 2019, ［International magazine］
  An efficient synthetic route to ( E)-1,3-bissilyl-6-arylfulvenes has been developed. The reaction of aryl iodides with trimethylsilylacetylene in the presence of a catalytic amount of PdBr2 gives 6-aryl-1,3-bis(trimethylsilyl)fulvenes in good to excellent yields with complete regio- and stereoselectivity. The reaction involves trimerization of trimethylsilylacetylene and cleavage of one silyl group. The silylated fulvenes obtained could be converted into halogenated fulvenes by site-selective halodesilylation. The halogenated fulvenes underwent the Stille coupling leading to the corresponding arylated fulvenes.
  English, Scientific journal
  DOI：https://doi.org/10.1021/acs.orglett.9b00144
  DOI ID：10.1021/acs.orglett.9b00144, PubMed ID：30789738
• Palladium-Catalyzed Regio- and Stereoselective Synthesis of (E)-1,3-Bissilyl-6-arylfulvenes from Aryl Iodides and Silylacetylenes　　　　　　　　　　　　　　　
  Souta Suzuki; Hidenori Kinoshita; Katsukiyo Miura
  ORGANIC LETTERS, Volume：21, Number：6, First page：1612, Last page：1616, Mar. 2019
  An efficient synthetic route to (E)-1,3-bissilyl-6-arylfulvenes has been developed. The reaction of aryl iodides with trimethylsilylacetylene in the presence of a catalytic amount of PdBr2 gives 6-aryl-1,3-bis(trimethylsilyl)fulvenes in good to excellent yields with complete regio- and stereoselectivity. The reaction involves trimerization of trimethylsilylacetylene and cleavage of one silyl group. The silylated fulvenes obtained could be converted into halogenated fulvenes by site-selective halodesilylation. The halogenated fulvenes underwent the Stille coupling leading to the corresponding arylated fulvenes.
  AMER CHEMICAL SOC, English, Scientific journal
  DOI：https://doi.org/10.1021/acs.orglett.9b00144
  DOI ID：10.1021/acs.orglett.9b00144, ISSN：1523-7060, eISSN：1523-7052, Web of Science ID：WOS:000461843900013
• 水素化ジイソブチルアルミニウムによる分子内炭素―炭素および炭素―ケイ素結合形成反応の開発　　　　　　　　　　　　　　　
  木下英典、三浦勝清
  有機合成化学協会誌, Volume：77, Number：1, First page：58, Last page：68, 2019
• Development of intramolecular C-C and C-Si bond forming reactions promoted by diisobutylaluminum hydride　　　　　　　　　　　　　　　
  Hidenori Kinoshita; Katsukiyo Miura
  Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry, First page：62, Last page：72, 2019
  Diisobutylaluminum hydride (DIBAL-H) is a common reagent in synthetic organic chemistry, and well known as a reducing agent of carbonyl groups and C-C multiple bonds. DIBAL-H is also used for modifications of alkynes. The preparation of haloalkenes via hydroalumination of alkynes and following halodemetallation of the resultant alkenylaluminums is the prime example. However, application of the alkenylaluminums to intramolecular bond formation remained largely unexplored. Recently, our attention has been focused on the reactivity and synthetic use of α - silylalkenylaluminums readly prepared from alkynylsilanes and DIBAL-H. During the course of our research, we succeeded in developing new cyclization reactions by DIBAL-H-promoted C-C and C-Si bond formation, which are valuable for regio-controlled syntheses of substituted benzenes, naphthalenes, indenes, benzosiloles, and siloles. These studies have provided not only efficient synthetic methods for carbocycles and silacycles but also novel information on the reactivity of organoaluminums.
  Scientific journal
  DOI：https://doi.org/10.5059/yukigoseikyokaishi.77.58
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  DOI ID：10.5059/yukigoseikyokaishi.77.58, ISSN：0037-9980, SCOPUS ID：85060898262
• Syntheses of substituted benzosiloles and siloles by diisobutylaluminium hydride-promoted cyclization of 1-silyl-2-(2-silylethynyl)benzenes and 1,4-disilylalk-3-en-1-ynes　　　　　　　　　　　　　　　
  Hidenori Kinoshita; Hiroki Fukumoto; Akihiro Ueda; Katsukiyo Miura
  Tetrahedron, Volume：74, Number：14, First page：1632, Last page：1645, Apr. 2018
  An efficient method for preparing substituted benzosiloles and unsymmetrically substituted siloles by intramolecular C-Si bond formation has been developed. The reaction of 1-methoxysilyl-2-[2-(trimethylsilyl)ethynyl]benzenes with 1.5 equiv of diisobutylaluminium hydride (DIBAL-H) gave benzosiloles in good to high yields. Similarly 4-methoxysilyl-1-silylalk-3-en-1-ynes were cyclized to multisubstituted siloles. Mechanistic study of this transformation uncovered that the methoxysilyl group was initially converted into the corresponding hydrosilyl group by the action of DIBAL-H, and that the resultant hydrosilanes underwent the DIBAL-H-promoted cyclization to benzosiloles. When 1-hydrosilyl-2-[2-(trimethylsilyl)ethynyl]benzenes were used as substrates, a substoichiometric amount of DIBAL-H was enough for the cyclization. The DIBAL-H-promoted transformation could be applied to regio-defined synthesis of unsymmetrically substituted siloles from 4-hydrosilyl-1-silylalk-3-en-1-ynes. This pre-installation approach provides a straightforward access to multisubstituted siloles with complete regioselection.
  Scientific journal
  DOI：https://doi.org/10.1016/j.tet.2018.02.011
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  DOI ID：10.1016/j.tet.2018.02.011, ISSN：0040-4020, eISSN：1464-5416, SCOPUS ID：85041948541
• Syntheses of substituted benzosiloles and siloles by diisobutylaluminium hydride-promoted cyclization of 1-sily1-2-(2-silylethynyl)benzenes and 1,4-disilylalk-3-en-1-ynes　　　　　　　　　　　　　　　
  Hidenori Kinoshita; Hiroki Fukumoto; Akihiro Ueda; Katsukiyo Miura
  TETRAHEDRON, Volume：74, Number：14, First page：1632, Last page：1645, Apr. 2018
  An efficient method for preparing substituted benzosiloles and unsymmetrically substituted siloles by intramolecular C-Si bond formation has been developed. The reaction of 1-methoxysilyl-2-[2-(trimethylsilyl)ethynyl]benzenes with 1.5 equiv of diisobutylaluminium hydride (DIBAL-H) gave benzosiloles in good to high yields. Similarly 4-methoxysilyl-1-silylalk-3-en-1-ynes were cyclized to multisubstituted siloles. Mechanistic study of this transformation uncovered that the methoxysilyl group was initially converted into the corresponding hydrosilyl group by the action of DIBAL-H, and that the resultant hydrosilanes underwent the DIBAL-H-promoted cyclization to benzosiloles. When 1-hydrosily1-2-[2-(trimethylsilyl)ethynyl]benzenes were used as substrates, a substoichiometric amount of DIBAL-H was enough for the cyclization. The DIBAL-H-promoted transformation could be applied to regio-defined synthesis of unsymmetrically substituted siloles from 4-hydrosilyl-1-silylalk-3-en-l-ynes. This pre-installation approach provides a straightforward access to multisubstituted siloles with complete regioselection. (C) 2018 Elsevier Ltd. All rights reserved.
  PERGAMON-ELSEVIER SCIENCE LTD, English, Scientific journal
  DOI：https://doi.org/10.1016/j.tet.2018.02.011
  DOI ID：10.1016/j.tet.2018.02.011, ISSN：0040-4020, Web of Science ID：WOS:000428484000004
• Diisobutylaluminum hydride-promoted cyclization of silylated 1,3-dien-5-ynes: Application to total synthesis of a 20-norabietane derivative　　　　　　　　　　　　　　　
  Hidenori Kinoshita; Kazuki Yaguchi; Takayuki Tohjima; Katsukiyo Miura
  TETRAHEDRON LETTERS, Volume：58, Number：16, First page：1607, Last page：1610, Apr. 2017, [Reviewed]
  The diisobutylaluminum hydride (DIBAL-H)-promoted benzocyclization, recently developed by this group, was adopted for the synthesis of a natural product containing a 9,10-dihydrophenanthrene skeleton to demonstrate its synthetic utility. One of the extracts from the roots of Salvia hydrangea DC. ex Bentham (Lamiaceae), a 20-norabietane derivative, was selected as the target molecule. The key step forming the 9,10-dihydrophenanthrene skeleton was achieved by the DIBAL-H-promoted cyclization of a silylated 1,3-dien-5-yne easily accessible from a substituted ot-tetralone. (C) 2017 Elsevier Ltd. All rights reserved.
  PERGAMON-ELSEVIER SCIENCE LTD, English, Scientific journal
  DOI：https://doi.org/10.1016/j.tetlet.2017.03.022
  DOI ID：10.1016/j.tetlet.2017.03.022, ISSN：0040-4039, Web of Science ID：WOS:000399258300017
• Diisobutylaluminunn Hydride Promoted Cyclization of 1-Hydrosilyl-4-silyl-1,3-enynes to Polysubstituted Siloles　　　　　　　　　　　　　　　
  Hidenori Kinoshita; Akihiro Ueda; Hirold Fukumoto; Katsukiyo Miura
  ORGANIC LETTERS, Volume：19, Number：4, First page：882, Last page：885, Feb. 2017, [Reviewed]
  An efficient method for preparing unsymmetrically multisubstituted siloles is described. The reaction of 1-hydrosilyl-4-silyl-1,3-enynes with diisobutylaluminum hydride (DIBAL-H) gave multisubstituted siloles in good to high yields. This method could be applied to the synthesis of benzosiloles using 2-hydrosilyl-1-(silylethynyl)benzenes as substrates. The silole formation was also promoted even by a substoichiometric amount of DIBAL-H. The reaction provides a straightforward method to prepare siloles and benzosiloles.
  AMER CHEMICAL SOC, English, Scientific journal
  DOI：https://doi.org/10.1021/acs.orglett.7600038
  DOI ID：10.1021/acs.orglett.7600038, ISSN：1523-7060, eISSN：1523-7052, Web of Science ID：WOS:000394736300036
• Cyclization of alk-5-ynyl ketones promoted by Tf2NH and In(OTf)(3): selective synthesis of 5-and 7-membered carbocycles　　　　　　　　　　　　　　　
  Hidenori Kinoshita; Chika Miyama; Katsukiyo Miura
  TETRAHEDRON LETTERS, Volume：57, Number：46, First page：5065, Last page：5069, Nov. 2016, [Reviewed]
  Combined use of Tf2NH and In(OTf)(3) effectively promotes the cyclization of allc-5-ynyl ketones to cyclopent-l-enyl ketones at 30 degrees C. Single use of Tf2NH or In(OTf)(3) requires heating at 50 degrees C for efficient cyclization. The In(OTf)(3)-promoted reaction of certain alk-5-ynyl ketones gives cyclohept-2-enones mainly. (C) 2016 Elsevier Ltd. All rights reserved.
  PERGAMON-ELSEVIER SCIENCE LTD, English, Scientific journal
  DOI：https://doi.org/10.1016/j.tetlet.2016.10.003
  DOI ID：10.1016/j.tetlet.2016.10.003, ISSN：0040-4039, Web of Science ID：WOS:000386862000012
• Diisobutylaluminum hydride-promoted cyclization of benzyl and phenylsilyl ethers bearing a 2-(trimethylsilyl)ethynyl group: syntheses of indenes and benzosiloles　　　　　　　　　　　　　　　
  Hidenori Kinoshita; Hiroki Fukumoto; Takayuki Tohjima; Katsukiyo Miura
  TETRAHEDRON LETTERS, Volume：57, Number：31, First page：3571, Last page：3574, Aug. 2016, [Reviewed]
  The reaction of o-[2-(trimethylsilyl)ethynyl]benzyl methyl ethers with diisobutylaluminum hydride (DIBAL-H) gave 2-(trimethylsilyl)indenes in good yields. This cyclization proceeds by regio- and stereos elective hydroalumination of the alkyne moiety followed by intramolecular nucleophilic substitution. o-[2-(Trimethylsilyl)ethynyl]phenylsilyl methyl ethers also underwent the. DIBAL-H promoted-cyclization to be converted into 2-(trimethylsilyl)benzosiloles in good yields. This approach provides straightforward and efficient way to construct benzosiloles from readily available organosilanes. (C) 2016 Elsevier Ltd. All rights reserved.
  PERGAMON-ELSEVIER SCIENCE LTD, English, Scientific journal
  DOI：https://doi.org/10.1016/j.tetlet.2016.06.123
  DOI ID：10.1016/j.tetlet.2016.06.123, ISSN：0040-4039, Web of Science ID：WOS:000380602300035
• Diisobutylaluminum hydride-promoted cyclization of o-(trimethylsilylethynyl)styrenes to substituted naphthalenes　　　　　　　　　　　　　　　
  Hidenori Kinoshita; Kazuki Yaguchi; Takayuki Tohjima; Nobuyoshi Hirai; Katsukiyo Miura
  TETRAHEDRON LETTERS, Volume：57, Number：19, First page：2039, Last page：2043, May 2016, [Reviewed]
  The reaction of alpha,beta-disubstituted (E)-o-(trimethylsilylethynyl)styrenes with a substoichiometric amount of diisobutylaluminum hydride at 100 degrees C gave 1,2,3-trisubstituted naphthalenes. This benzocyclization is initiated by regioselective hydroalumination of the alkyne moiety, and the resultant alkenylaluminums lead to naphthalenes through intramolecular carboalumination, skeletal rearrangement, and dehydroalumination steps. The silylated products could be efficiently transformed into iodinated polycyclic aromatic hydrocarbons. (C) 2016 Elsevier Ltd. All rights reserved.
  PERGAMON-ELSEVIER SCIENCE LTD, English, Scientific journal
  DOI：https://doi.org/10.1016/j.tetlet.2016.03.099
  DOI ID：10.1016/j.tetlet.2016.03.099, ISSN：0040-4039, Web of Science ID：WOS:000375338700006
• Regioselective Allylation of Carbon Electrophiles with Alkenylsilanes under Dual Catalysis by Cationic Platinum(II) Species　　　　　　　　　　　　　　　
  Hidenori Kinoshita; Ryosuke Kizu; Masahiro Horikoshi; Gen Inoue; Masayuki Fujimoto; Masanori Saito; Junji Ichikawa; Akira Hosomi; Katsukiyo Miura
  SYNTHESIS-STUTTGART, Volume：48, Number：4, First page：520, Last page：534, Feb. 2016, [Reviewed]
  In the presence of catalytic amounts of platinum(II) chloride and silver(I) hexafluoroantimonate, (Z)-alkenylsilanes reacted with various carbon electrophiles (acetals, aminals, carboxylic anhydrides, alkyl chlorides, etc.) at the -position to give allylation products. A plausible mechanism for the platinum-catalyzed allylation involves alkene migration of alkenylsilanes to allylsilanes and subsequent allylation of carbon electrophiles, both of which are catalyzed by a cationic platinum(II) species.
  GEORG THIEME VERLAG KG, English, Scientific journal
  DOI：https://doi.org/10.1055/s-0035-1560380
  DOI ID：10.1055/s-0035-1560380, ISSN：0039-7881, eISSN：1437-210X, Web of Science ID：WOS:000369749600005
• Platinum-Catalyzed Allylation of Carbon Electrophiles with Alkenylsilanes　　　　　　　　　　　　　　　
  Kinoshita,Hidenori; Kizu,Ryosuke; Inoue,Gen; Fujimoto,Masayuki; Saito,Masanori; Ichikawa,Junji; Hosomi,Akira; Miura,Katsukiyo
  Tetrahedron Letters, Volume：56, Number：5, First page：713, Last page：716, Jan. 2015, [Reviewed]
  In the presence of catalytic amounts of PtCl2 and AgSbF6, (Z)-alkenylsilanes react with various carbon electrophiles at the γ-position to give allylation products. A plausible mechanism for the Pt-catalyzed allylation involves alkene migration of alkenylsilanes to allylsilanes and subsequent allylation of carbon electrophiles.
  ELSEVIER, English, Scientific journal
  DOI：https://doi.org/10.1016/j.tetlet.2014.12.077
  Scopus：https://www.scopus.com/inward/record.uri?partnerID=HzOxMe3b&scp=84920749622&origin=inward
  Scopus Citedby：https://www.scopus.com/inward/citedby.uri?partnerID=HzOxMe3b&scp=84920749622&origin=inward
  DOI ID：10.1016/j.tetlet.2014.12.077, ISSN：0040-4039, eISSN：1873-3581, SCOPUS ID：84920749622
• Hydroalumination-Triggered Cyclization of Silylated 1,3-Dien-5-ynes to Polysubstituted Benzenes　　　　　　　　　　　　　　　
  Hidenori Kinoshita; Takayuki Tohjima; Katsukiyo Miura
  ORGANIC LETTERS, Volume：16, Number：18, First page：4762, Last page：4765, Sep. 2014, [Reviewed]
  Regiocontrolled synthesis of polysubstituted benzenes from silylated 1,3-dien-5-ynes has been achieved by using diisobutylaluminum hydride (DIBAL-H). Hydroalumination of the alkyne moiety with DIBAL-H triggers the aromatic cyclization, which usually proceeds without rearrangement and loss of the existing substituents. The related unusual cyclizations to different types of polysubstituted benzenes are also described.
  AMER CHEMICAL SOC, English, Scientific journal
  DOI：https://doi.org/10.1021/ol5022096
  DOI ID：10.1021/ol5022096, ISSN：1523-7060, eISSN：1523-7052, Web of Science ID：WOS:000342117600018
• Diisobutylaluminum Hydride Promoted Cyclization of o-(Trimethylsilylethynyl)styrenes to Indenes　　　　　　　　　　　　　　　
  Hidenori Kinoshita; Nobuyoshi Hirai; Katsukiyo Miura
  JOURNAL OF ORGANIC CHEMISTRY, Volume：79, Number：17, First page：8171, Last page：8181, Sep. 2014, [Reviewed]
  The reaction of o-(trimethylsilylethynyl)styrenes with diisobutylaluminum hydride (DIBAL-H) provides 2-trimethylsilyl-1H-indenes efficiently. The cyclization mechanism involves regioselective hydroalumination of the alkynyl moiety, geometrical isomerization of the alkenylaluminums formed, and intramolecular carboalumination. With substrates bearing a 2-(trimethylsilyl)ethenyl group (R-1 = Me3Si, R-2 = R-3 = H), bis-silylated benzofulvenes are obtained upon treatment of the reaction mixture with an excess amount of benzaldehyde.
  AMER CHEMICAL SOC, English, Scientific journal
  DOI：https://doi.org/10.1021/jo501383v
  DOI ID：10.1021/jo501383v, ISSN：0022-3263, Web of Science ID：WOS:000341345400040
• Platinum-catalyzed one-pot alkenylation of aldehydes using alkynes and triethylsilane: Dual catalysis by platinum(II) chloride　　　　　　　　　　　　　　　
  Hidenori Kinoshita; Ryousuke Uemura; Daiki Fukuda; Katsukiyo Miura
  Organic Letters, Volume：15, Number：21, First page：5538, Last page：5541, Nov. 2013
  The PtCl2-catalyzed hydrosilylation of terminal alkynes with triethylsilane and subsequent alkenylation of aldehydes with the resultant (E)-alkenylsilanes in a one-pot manner are described. By adding p-benzoquinone and LiI, the latter alkenylation step proceeds smoothly to give allyl silyl ethers in moderate to high yields. This one-pot alkenylation is tolerant to a reasonable range of functional groups. PtCl2 plays a dual role as hydrosilylation and alkenylation catalysts. © 2013 American Chemical Society.
  Scientific journal
  DOI：https://doi.org/10.1021/ol4026952
  Scopus：https://www.scopus.com/inward/record.uri?partnerID=HzOxMe3b&scp=84887051678&origin=inward
  Scopus Citedby：https://www.scopus.com/inward/citedby.uri?partnerID=HzOxMe3b&scp=84887051678&origin=inward
  DOI ID：10.1021/ol4026952, ISSN：1523-7060, eISSN：1523-7052, SCOPUS ID：84887051678
• Platinum-Catalyzed One-Pot Alkenylation of Aldehydes Using Alkynes and Triethylsilane: Dual Catalysis by Platinum(II) Chloride　　　　　　　　　　　　　　　
  Hidenori Kinoshita; Ryousuke Uemura; Daiki Fukuda; Katsukiyo Miura
  ORGANIC LETTERS, Volume：15, Number：21, First page：5538, Last page：5541, Nov. 2013
  The PtCl2-catalyzed hydrosilylation of terminal alkynes with triethylsilane and subsequent alkenylation of aldehydes with the resultant (E)-alkenylsilanes in a one-pot manner are described. By adding p-benzoquinone and Lil, the latter alkenylation step proceeds smoothly to give allyl silyl ethers in moderate to high yields. This one-pot alkenylation is tolerant to a reasonable range of functional groups. PtCl2 plays a dual role as hydrosilylation and alkenylation catalysts.
  AMER CHEMICAL SOC, English, Scientific journal
  DOI：https://doi.org/10.1021/ol4026952
  DOI ID：10.1021/ol4026952, ISSN：1523-7060, eISSN：1523-7052, Web of Science ID：WOS:000326615100037
• Platinum-catalyzed one-pot alkenylation of aldehydes using alkynes and triethylsilane: dual catalysis by platinum(II) chloride.　　　　　　　　　　　　　　　
  Hidenori Kinoshita; Ryousuke Uemura; Daiki Fukuda; Katsukiyo Miura
  Organic letters, Volume：15, Number：21, First page：5538, Last page：41, Nov. 2013, ［International magazine］
  The PtCl2-catalyzed hydrosilylation of terminal alkynes with triethylsilane and subsequent alkenylation of aldehydes with the resultant (E)-alkenylsilanes in a one-pot manner are described. By adding p-benzoquinone and LiI, the latter alkenylation step proceeds smoothly to give allyl silyl ethers in moderate to high yields. This one-pot alkenylation is tolerant to a reasonable range of functional groups. PtCl2 plays a dual role as hydrosilylation and alkenylation catalysts.
  English, Scientific journal
  DOI：https://doi.org/10.1021/ol4026952
  DOI ID：10.1021/ol4026952, PubMed ID：24147871
• Nucleophilic Addition of alpha-(Dimethylsilyl)nitriles to Aldehydes and Ketones　　　　　　　　　　　　　　　
  Jinzaki, Takaaki; Arakawa, Mitsuru; Kinoshita, Hidenori; Ichikawa, Junji; Miura, Katsukiyo
  ORGANIC LETTERS, Volume：15, Number：14, First page：3750, Last page：3753, Jul. 2013, [Reviewed], ［International magazine］
  α-Alkylated (dimethylsilyl)acetonitriles (Me2HSiCR(3)R(4)CN) react spontaneously with aldehydes in DMSO to give β-hydroxynitriles in good to high yields. The addition to ketones is effectively promoted by using MgCl2 or CaCl2. (Dimethylsilyl)acetonitrile (Me2HSiCH2CN) shows lower reactivity than the α-alkylated analogues. However, the parent reagent adds efficiently to aldehydes and ketones under catalysis by AcOLi or MgCl2.
  AMER CHEMICAL SOC, English, Scientific journal
  DOI：https://doi.org/10.1021/ol401663u
  DOI ID：10.1021/ol401663u, ISSN：1523-7060, PubMed ID：23837593
• Regioselective Synthesis of Multisubstituted Benzenes by Palladium-Catalyzed Intermolecular Reaction of beta-lodo/beta-silylstyrenes with Alkynes　　　　　　　　　　　　　　　
  Hidenori Kinoshita; Hirotoshi Takahashi; Katsukiyo Miura
  ORGANIC LETTERS, Volume：15, Number：12, First page：2962, Last page：2965, Jun. 2013, [Reviewed]
  The Pd-catalyzed reaction between beta-iodo-beta-silyistyrenes and terminal alkynes in i-Pr2NEt gave 1,2,3,5-tetrasubstituted benzenes with complete regioselection. The use of certain silylacetylenes as alkynes enabled efficient synthesis of 1,3,5-trissilyl-2-arylbenzenes, which could be transformed into other multisubstituted benzenes by displacement of the silyl groups.
  AMER CHEMICAL SOC, English, Scientific journal
  DOI：https://doi.org/10.1021/ol4010883
  DOI ID：10.1021/ol4010883, ISSN：1523-7060, eISSN：1523-7052, Web of Science ID：WOS:000320979000019
• 有機ケイ素反応剤を利用する新規炭素–炭素結合形成反応の開発　　　　　　　　　　　　　　　
  三浦勝清
  ケイ素化学協会誌, Number：30, First page：5, Last page：12, 2013
• Synthetic utility of tribenzyltin hydride and its derivatives as easily accessible, removable, and decomposable organotin reagents　　　　　　　　　　　　　　　
  Takeshi Yamakawa; Hidenori Kinoshita; Katsukiyo Miura
  JOURNAL OF ORGANOMETALLIC CHEMISTRY, Volume：724, Number：1, First page：129, Last page：134, Jan. 2013, [Reviewed]
  Radical reactions using tribenzyltin hydride (Bn3SnH) easily prepared from tin and benzyl chloride were studied. The Et3B-initiated reduction and cyclization of haloalkanes and haloalkenes with Bn3SnH proceeded efficiently. Homolytic hydrostannylation of alkynes with Bn3SnH followed by treatment with electrophiles gave functionalized alkenes in good to high yields. The organotin byproducts formed could be easily removable by filtration and silica-gel column chromatography without any pretreatment. It was also found that tribenzyltin chloride (Bn3SnCl) easily decomposed to benzyl alcohol in a basic solution of H2O2. (C) 2012 Elsevier B. V. All rights reserved.
  ELSEVIER SCIENCE SA, English, Scientific journal
  DOI：https://doi.org/10.1016/j.jorganchem.2012.11.007
  DOI ID：10.1016/j.jorganchem.2012.11.007, ISSN：0022-328X, eISSN：1872-8561, Web of Science ID：WOS:000314113400017
• Dialkylaluminum Hydride-Promoted Cyclodimerization of Silylated 1,3-Enynes via Skeletal Rearrangement　　　　　　　　　　　　　　　
  Hidenori Kinoshita; Tomoyuki Ishikawa; Katsukiyo Miura
  ORGANIC LETTERS, Volume：13, Number：23, First page：6192, Last page：6195, Dec. 2011, [Reviewed]
  The dialkylaluminum hydride-promoted reaction of 1-silylalk-3-en-1-ynes gave symmetrical 1,2,3,5-tetrasubstituted benzenes as single regiolsomers. The novel cyclodimerization via skeletal rearrangement can be rationalized by an unprecedented mechanism Involving sequential hydroalumination, alkene isomerization, carboalumination, carbon-carbon bond cleavage, and retro-hydroalumination.
  AMER CHEMICAL SOC, English, Scientific journal
  DOI：https://doi.org/10.1021/ol202601s
  DOI ID：10.1021/ol202601s, ISSN：1523-7060, Web of Science ID：WOS:000297274700015
• トピックス①：ケイ素-炭素結合の活性化に基づく新規有機合成反応の開発　　　　　　　　　　　　　　　
  三浦勝清
  Organometallic News, Number：3, First page：59, 2011
• Indium(III)-catalyzed Coupling between Alkynes and Aldehydes to α,β-Unsaturated Ketones　　　　　　　　　　　　　　　
  Miura, Katsukiyo; Yamamoto, Kiyomi; Yamanobe, Aya; Ito, Keisuke; Kinoshita, Hidenori; Ichikawa, Junji; Hosomi, Akira
  CHEMISTRY LETTERS, Volume：39, Number：7, First page：766, Last page：767, Jul. 2010, [Reviewed]
  CHEMICAL SOC JAPAN, English, Scientific journal
  DOI ID：10.1246/cl.2010.766, ISSN：0366-7022, CiNii Articles ID：10027183129, CiNii Books ID：AA00603318
• 十字路：高配位スズ中間体　　　　　　　　　　　　　　　
  三浦勝清
  有機合成化学協会誌, Volume：66, Number：1, First page：76, Jan. 2008
  有機合成化学協会, Scientific journal
• Indium-catalyzed radical reductions of organic halides with hydrosilanes　　　　　　　　　　　　　　　
  Katsukiyo Miura; Mitsuru Tomita; Yusuke Yamada; Akira Hosomi
  JOURNAL OF ORGANIC CHEMISTRY, Volume：72, Number：3, First page：787, Last page：792, Feb. 2007, [Reviewed]
  The In(OAc)(3)-catalyzed reaction of bromo- and iodoalkanes with PhSiH3 in THF at 70 degrees C gave dehalogenated alkanes in good to high yields. In the presence of Et3B and air, the reduction proceeded smoothly at 30 degrees C. When 2,6-lutidine and air were used as additives, the In(OAc)(3)-catalyzed system enabled an efficient reduction of simple and functionalized iodoalkanes in EtOH. Catalytic use of GaCl3 was found to be effective in the reduction of haloalkanes with poly(methylhydrosiloxane) (PMHS). These catalytic reductions probably involve a radical chain mechanism in which indium or gallium hydride species work as the actual reductants.
  AMER CHEMICAL SOC, English, Scientific journal
  DOI：https://doi.org/10.1021/jo061880o
  DOI ID：10.1021/jo061880o, ISSN：0022-3263, Web of Science ID：WOS:000243735500014
• Homolytic hydrogermylation of alkenes with dibutylchlorogermane　　　　　　　　　　　　　　　
  Katsukiyo Miura; Kazunori Ootsuka; Akira Hosomi
  JOURNAL OF ORGANOMETALLIC CHEMISTRY, Volume：692, Number：1-3, First page：514, Last page：519, Jan. 2007, [Reviewed]
  In the presence of Et3B-dry air, dibutylchlorogermane (Bu2GeClH) reacted smoothly with alkenes at room temperature to give hydrogermylation products in high yields. This homolytic hydrogermylation was applicable to various alkenes including electron-deficient, electron-rich, and internal alkenes. Under the same conditions, tributylgermane (Bu3GeH) showed much lower reactivity than Bu2GeClH. The Et3B-initiated reaction of 1,6-dienes with Bu2GeClH gave germylmethylated cyclopentanes. (c) 2006 Elsevier B.V. All rights reserved.
  ELSEVIER SCIENCE SA, English, Scientific journal
  DOI：https://doi.org/10.1016/j.jorganchem.2006.04.043
  DOI ID：10.1016/j.jorganchem.2006.04.043, ISSN：0022-328X, Web of Science ID：WOS:000243859700062
• Indium(III) salt promoted intramolecular addition of allylsilanes to unactivated alkynes　　　　　　　　　　　　　　　
  Katsukiyo Miura; Naoki Fujisawa; Sayaka Toyohara; Akira Hosomi
  SYNLETT, Number：12, First page：1883, Last page：1886, Aug. 2006, [Reviewed]
  In the presence of a stoichiometric or catalytic amount of a Lewis acidic indium(III) salt, allylsilanes reacted intramolecularly with unactivated terminal alkynes to give cyclized products in good to high yields. The fact that the reaction proceeded in a trans-addition mode suggests a reaction mechanism via electrophilic activation of the triple bond by the indium salt.
  GEORG THIEME VERLAG KG, English, Scientific journal
  DOI：https://doi.org/10.1055/s-2006-947348
  DOI ID：10.1055/s-2006-947348, ISSN：0936-5214, Web of Science ID：WOS:000240009100016
• Synthetic radical reactions using dibutylchlorogermane and dibutylethoxygermane as radical mediators　　　　　　　　　　　　　　　
  Katsukiyo Miura; Kazunori Ootsuka; Akira Hosomi
  Synlett, Number：20, First page：3151, Last page：3153, Dec. 2005, [Reviewed]
  In the presence of Et3B as radical initiator, dibutylchlorogermane (1a) and dibutylethoxygermane (1b) reacted with bromo- and iodoalkanes at room temperature to give the corresponding alkanes in high yields. Hydrogermane 1a was more reactive than 1b. However, 1b worked as a better radical mediator in intermolecular radical addition of haloalkanes to electron-deficient alkenes. © Georg Thieme Verlag Stuttgart.
  English, Scientific journal
  DOI：https://doi.org/10.1055/s-2005-921927
  DOI ID：10.1055/s-2005-921927, ISSN：0936-5214, SCOPUS ID：29744457086
• Development of new reagents containing silicon and related metals and application to practical organic syntheses　　　　　　　　　　　　　　　
  Akira Hosomi; Katsukiyo Miura
  Bulletin of the Chemical Society of Japan, Volume：77, Number：5, First page：835, Last page：851, 2004, [Reviewed]
  Our research works in the last few decades are summarized. We have studied the synthetic use of organometallics, especially organosilicon compounds, and have developed a number of new reagents and reactions useful for efficient organic synthesis. In the first section, the allylation of carbon electrophiles with allylsilanes, the so-called Hosomi-Sakurai reaction, is described. We have demonstrated that the allylation reaction is valuable not only for highly regio- and stereoselective carbon-carbon bond formation but also for introduction of a variety of functionalities. The second section deals with synthetic reactions using highly coordinated organosilanes and other organometallics, including Cr, Mn, Fe, and Cu. Higher coordination by one or more extra anionic ligands brings about unique reactivities that enable synthetically useful transformations. As shown in the third section, we developed stable 1,3-dipole equivalents protected by a silyl group and their cycloadditions, leading to N, S, or O-containing heterocycles. The following section describes the stereoselective synthesis of cyclic ethers and amines by acid-catalyzed cyclizations of vinylsilanes bearing a hydroxy or amino group. These silicon-directed cyclizations have disclosed the synthetic utility of β-silylcarbenium ion species generated from vinylsilanes by protonation. The copper-catalyzed reactions of organosilanes via silicon-copper exchange are described in the fifth section. In the final section, our studies on homolytic carbometalation reactions are presented.
  English, International conference proceedings
  DOI：https://doi.org/10.1246/bcsj.77.835
  DOI ID：10.1246/bcsj.77.835, ISSN：0009-2673, SCOPUS ID：2642585825
• Acid-catalyzed intramolecular addition of a carboxy group to vinylsilanes　　　　　　　　　　　　　　　
  Katsukiyo Miura; Joji Hayashida; Tatsuyuki Takahashi; Hisashi Nishikori; Akira Hosomi
  Journal of Organometallic Chemistry, Volume：686, Number：1-2, First page：242, Last page：250, Dec. 2003
  In the presence of a catalytic amount of TsOH·H2O or TiCl4, 5-silyl-4-pentenoic acids (1), namely vinylsilanes with a carboxy group, were smoothly cyclized to γ-lactones in good to high yields. The difference in the geometry of the carbon-carbon double-bond did not affect the reaction rate. The TiCl4-catalyzed cyclization of the substrates bearing a phenyl or alkyl group at the homoallylic position showed moderate cis -selectivity, while introduction of a substituent into the allylic position led to high trans-selectivity. © 2003 Elsevier Science B.V. All rights reserved.
  English, Scientific journal
  DOI：https://doi.org/10.1016/S0022-328X(03)00533-3
  DOI ID：10.1016/S0022-328X(03)00533-3, ISSN：0022-328X, SCOPUS ID：0142120324
• Stereoselective synthesis of substituted cyclic ethers and amines by acid-catalyzed cyclization of vinylsilanes bearing a hydroxy or amino group　　　　　　　　　　　　　　　
  Katsukiyo Miura; Akira Hosomi
  Synlett, Number：2, First page：143, Last page：155, 2003
  This account summarizes our recent study on the silicon-directed cyclization of vinylsilanes bearing a heteroatom nucleophile (OH, NHZ) via β-silylcarbenium ion intermediates. In the presence of an acid catalyst, 5-silyl-4-penten-1-ols (1) are cyclized to 2-(silylmethyl)tetrahydrofurans (2) by a stereospecific syn addition of the hydroxy group. (Z)-Vinylsilanes 1 are more reactive toward cyclization than their E-isomers. Introduction of a substituent to the methylene tether of (Z)-1 enables the stereoselective synthesis of 2,n-disubstituted tetrahydrofurans (n = 3-5). This cyclization also provides a new route to 1,3-dioxanes using hemiacetals prepared from (Z)-4-silyl-3-buten-1-ols (13) and chloral. In contrast to the results with α-unsubstituted vinylsilanes 1, the acid-catalyzed cyclization of (Z)-5-alkyl-5-silyl-4-penten-1-ols [(Z)-15] gives 2-alkyl-3-silyltetrahydropyrans (16) with high trans-selectivity, while the 1,2-silyl-migrative cyclization of (E)-15 proceeds with low cis-selectivity. Both geometrical isomers of 4-alkyl-4-silyl-3-buten-1-ols (18) also undergo the stereospecific cyclization to afford 2-alkyl-3-silyltetrahydrofurans (19) with high diastereoselectivity. The 1,2-silyl-migrative cyclization is applicable to the stereoselective synthesis of trisubstituted tetrahydropyrans and tetrahydrofurans. The acid-catalyzed reactions of 4-silyl-4-nonen-1-ols (25) and 3-benzyldimethylsilyl-3-octen-1-ol (26) form tetrahydropyrans 16 and tetrahydrofuran 19c by a stereospecific endo-cyclization. Like a hydroxy group, amino groups protected by an electron-withdrawing group can intramolecularly add to vinylsilanes with the aid of an acid catalyst. This cyclization is valuable for the stereoselective synthesis of pyrrolidines and piperidines. The silylated products, obtained by the above cyclizations, can be converted to the corresponding alcohols by oxidative cleavage of the Si-C bond. 1. Introduction 2. Cyclization of α-Unsubstituted Vinylsilanes Bearing a Hydroxy Group 3. Cyclization of Vinylsilanes Bearing a Hemiacetal Group 4. 1,2-Silyl-Migrative Cyclization of α-Substituted Vinylsilanes Bearing a Hydroxy Group 5. endo-Cyclization of Vinylsilanes Bearing a Hydroxy Group 6. Cyclization of Vinylsilanes Bearing an Amino Group 7. Oxidative Removal of Silyl Groups of Cyclized Products 8. Conclusion.
  Georg Thieme Verlag, English, Scientific journal
  DOI：https://doi.org/10.1055/s-2003-36776
  DOI ID：10.1055/s-2003-36776, ISSN：0936-5214, SCOPUS ID：0037286925
• Lewis acid-catalyzed reductive etherification of carbonyl compounds with alkoxyhydrosilanes　　　　　　　　　　　　　　　
  Katsukiyo Miura; Kazunori Ootsuka; Shuntaro Suda; Hisashi Nishikori; Akira Hosomi
  Synlett, Number：2, First page：313, Last page：315, 2002
  The TMSI-catalyzed reaction of aldehydes and ketones with alkoxydimethylsilanes gave unsymmetrical ethers in good to high yields. This reductive etherification is superior to the conventional method using two kinds of silicon reagents in terms of atom efficiency and ease of operation.
  Georg Thieme Verlag, English, Scientific journal
  DOI：https://doi.org/10.1055/s-2002-19779
  DOI ID：10.1055/s-2002-19779, ISSN：0936-5214, SCOPUS ID：0036172530
• Synthetic utility of stannyl enolates as radical alkylating agents　　　　　　　　　　　　　　　
  Katsukiyo Miura; Naoki Fujisawa; Hiroshi Saito; Di Wang; Akira Hosomi
  Organic Letters, Volume：3, Number：16, First page：2591, Last page：2594, Aug. 2001, [Reviewed]
  (Equation presented) The radical-initiated β-ketoalkylation of haloalkanes with tributylstannyl enolates is described. Stannyl enolates derived from aromatic ketones are reactive toward the homolytic β-ketoalkylation of simple haloalkanes as well as those activated by an electron-withdrawing group. The reactivity of stannyl enolates as radical alkylating agents can be utilized for an efficient three-component coupling reaction among stannyl enolates, haloalkanes, and electron-deficient alkenes.
  English, Scientific journal
  DOI：https://doi.org/10.1021/ol016268s
  DOI ID：10.1021/ol016268s, ISSN：1523-7060, PubMed ID：11483068, SCOPUS ID：0000369094
• Tandem Aldol-Reduction Reaction of Dimethylsilyl Enolates:A New Method for Stereoselective Preparation of 1, 3-Diols　　　　　　　　　　　　　　　
  MIURA Katsukiyo; NAKAGAWA Takahiro; SUDA Shuntaro; HOSOMI Akira
  Chemistry Letters, Volume：2000, Number：2, First page：150, Last page：151, Feb. 2000
  In the presence of a catalytic amount of TBAF (Bu₄NF), dimethylsilyl enolates derived from acyclic ketones reacted with aldehydes to give syn,syn-1,3-diols 7a and 8a with moderate to high diastereoselectivity. The stereochemical outcome can be attributed to a syn-selective aldol reaction and the subsequent 1,2-syn-selective intramolecular reduction.
  The Chemical Society of Japan, English
  DOI：https://doi.org/10.1246/cl.2000.150
  DOI ID：10.1246/cl.2000.150, ISSN：0366-7022, CiNii Articles ID：10004694047, CiNii Books ID：AA00603318
• Hydroxy Group-Directed Homolytic Hydrostannylation of Alkenols with Dibutylchlorostannane　　　　　　　　　　　　　　　
  MIURA Katsukiyo; SAITO Hiroshi; UCHINOKURA Shingo; HOSOMI Akira
  Chemistry Letters, Volume：1999, Number：7, First page：659, Last page：660, Jul. 1999
  In homolytic hydrostannylation of allyl alcohol 1a or homoallyl alcohol 1b, dibutylchlorostannane (Bu₂ClSnH) exhibited a much higher reactivity than tributylstannane (Bu₃SnH). Competitive reaction of 1a vs. 1-octene with Bu₂ClSnH led to the selective formation of γ-stannylated alcohol 3a. Hydrostannylation of 1,5-hexadien-3-ol (8) with Bu₂ClSnH favored 1-stannylated product 9 over 6-stannylated product 10, while the use of Bu₃SnH decreased the regioselectivity.
  The Chemical Society of Japan, English
  DOI：https://doi.org/10.1246/cl.1999.659
  DOI ID：10.1246/cl.1999.659, ISSN：0366-7022, CiNii Articles ID：10004702308, CiNii Books ID：AA00603318
• Uncatalyzed aldol reaction using a dimethylsilyl enolate and alpha-dimethylsilyl ester in N,N-dimethylformamide　　　　　　　　　　　　　　　
  K Miura; H Sato; K Tamaki; H Ito; A Hosomi
  TETRAHEDRON LETTERS, Volume：39, Number：17, First page：2585, Last page：2588, Apr. 1998, [Reviewed]
  Dimethylsilyl enolates and alpha-dimethylsilyl esters reacted with aldehydes in N,N-dimethyl-formamide without an activator to give aldol adducts in moderate to good yields. Under the same conditions, the corresponding trimethylsilyl derivatives exhibited lower reactivities toward the aldol reaction. (C) 1998 Elsevier Science Ltd. All rights reserved.
  PERGAMON-ELSEVIER SCIENCE LTD, English, Scientific journal
  DOI：https://doi.org/10.1016/S0040-4039(98)00275-5
  DOI ID：10.1016/S0040-4039(98)00275-5, ISSN：0040-4039, ORCID：13020655, SCOPUS ID：0032560067, Web of Science ID：WOS:000072999900041
• Studies on organosilicon chemistry. 138. Generation of a reducing reagent from copper(I) salt and hydrosilane. New practical method for conjugate reduction　　　　　　　　　　　　　　　
  H Ito; T Ishizuka; K Arimoto; K Miura; A Hosomi
  TETRAHEDRON LETTERS, Volume：38, Number：51, First page：8887, Last page：8890, Dec. 1997, [Reviewed]
  Hydride transfer from a hydrosilane to a copper(I) salt is reported. The silicon group of hydrosilanes was smoothly replaced by copper(I) chloride in DMI to give the corresponding metal hydride complex of copper(I). This transformation was applied to conjugate reduction of alpha,beta-unsaturated compounds with a hydrosilane mediated by copper(I) chloride. (C) 1997 Elsevier Science Ltd.
  PERGAMON-ELSEVIER SCIENCE LTD, English, Scientific journal
  DOI：https://doi.org/10.1016/S0040-4039(97)10326-4
  DOI ID：10.1016/S0040-4039(97)10326-4, ISSN：0040-4039, ORCID：13020656, SCOPUS ID：0030733481, Web of Science ID：WOS:A1997YK20700030
• Highly Stereoselective Intramolecular Addition of a Hydroxyl Group to Vinylsilanes via 1,2-Silyl Migration　　　　　　　　　　　　　　　
  Katsukiyo Miura; Takeshi Hondo; Hiroshi Saito; Hajime Ito; Akira Hosomi
  Journal of Organic Chemistry, Volume：62, Number：24, First page：8292, Last page：8293, 1997
  American Chemical Society, English, Scientific journal
  DOI：https://doi.org/10.1021/jo971847p
  DOI ID：10.1021/jo971847p, ISSN：0022-3263, SCOPUS ID：0000897326
• Titanocene- and zirconocene-mediated cyclization of allyl propargyl ethers. Stereoselective synthesis of 3-methylenetetrahydrofurans　　　　　　　　　　　　　　　
  K Miura; M Funatsu; H Saito; H Ito; A Hosomi
  TETRAHEDRON LETTERS, Volume：37, Number：50, First page：9059, Last page：9062, Dec. 1996, [Reviewed]
  Low-valent titanium and zirconium reagents in situ prepared from metallocene dichlorides (Cp(2)MCl(2): M = Ti, Zr) and magnesium powder activated by 1,2-dibromoethane smoothly reacted with allyl propargyl ethers to afford 3-methylenetetrahydrofurans in good yields. It is noteworthy that the Cp(2)Zr- and Cp(2)Ti-mediated cyclizations proceed with inverse stereoselectivity. Copyright (C) 1996 Elsevier Science Ltd
  PERGAMON-ELSEVIER SCIENCE LTD, English, Scientific journal
  DOI：https://doi.org/10.1016/S0040-4039(96)02128-4
  DOI ID：10.1016/S0040-4039(96)02128-4, ISSN：0040-4039, ORCID：13020663, SCOPUS ID：0030577472, Web of Science ID：WOS:A1996VY07300028
• Allylstannylation of alkynes via a radical process: Stereoselective synthesis of di- and tri-substituted vinylstannanes　　　　　　　　　　　　　　　
  K Miura; D Itoh; T Hondo; H Saito; H Ito; A Hosomi
  TETRAHEDRON LETTERS, Volume：37, Number：47, First page：8539, Last page：8542, Nov. 1996, [Reviewed]
  In the presence of AIBN, allylstannanes bearing an electron-withdrawing group at the beta-position easily reacted with terminal and electron-deficient internal alkynes to give beta-allylsubstituted vinylstannanes in moderate to good yields. The allylstannylation proceeds with anti addition exclusively. Copyright (C) 1996 Elsevier Science Ltd
  PERGAMON-ELSEVIER SCIENCE LTD, English, Scientific journal
  DOI：https://doi.org/10.1016/0040-4039(96)01986-7
  DOI ID：10.1016/0040-4039(96)01986-7, ISSN：0040-4039, ORCID：13020667, SCOPUS ID：0030592707, Web of Science ID：WOS:A1996VU40500023
• Allylstannylation of alkenes via radical process　　　　　　　　　　　　　　　
  K Miura; T Matsuda; T Hondo; H Ito; A Hosomi
  SYNLETT, Volume：1996, Number：6, First page：555, Last page：&, Jun. 1996, [Reviewed]
  Allylstannanes bearing an electron-withdrawing group at the beta-position easily reacted with various electron-deficient alkenes to introduce both allyl and stannyl groups.
  GEORG THIEME VERLAG, English, Scientific journal
  DOI：https://doi.org/10.1055/s-1996-5501
  DOI ID：10.1055/s-1996-5501, ISSN：0936-5214, ORCID：13020664, SCOPUS ID：0002202114, Web of Science ID：WOS:A1996UR01300026
• ENE PREFERENCE IN THE REACTION OF ALLENYLMETHYLSILANES WITH HETERO-DOUBLE BONDS MEDIATED BY A LEWIS-ACID　　　　　　　　　　　　　　　
  M HOJO; C MURAKAMI; H AIHARA; K TOMITA; K MIURA; A HOSOMI
  JOURNAL OF ORGANOMETALLIC CHEMISTRY, Volume：499, Number：1-2, First page：155, Last page：157, Sep. 1995
  Methylthio- and methoxy-substituted allenylmethylsilanes, a kind of allylsilanes, undergo the ene-type reaction, not the usual allylsilane-type reaction accompanying by desilylation, with carbonyl and azo compounds mediated by a Lewis acid. The corresponding 1-silyl-substituted functionalized 1,3-dienes are obtained in good yields.
  ELSEVIER SCIENCE SA LAUSANNE, English, Scientific journal
  DOI：https://doi.org/10.1016/0022-328X(95)00306-B
  DOI ID：10.1016/0022-328X(95)00306-B, ISSN：0022-328X, Web of Science ID：WOS:A1995RR62400022
• Nucleophile-Induced Ring Enlargement of 1-(1-Iodoalkyl) silacyclobutane and 1-(1,2-Epoxyalkyl)silacyclobutane into Silacyclopentane. Application to the Syntheses of 1,4-Diol, 4-Alken-1-ol, and 1,4,5-Triol.　　　　　　　　　　　　　　　
  Matsumoto Kozo; Takeyama Yoshihiro; Miura Katsukiyo; Oshima Koichiro; Utimoto Kiitiro
  Bull. Chem. Soc. Jpn., Volume：68, Number：1, First page：250, Last page：261, 1995
  Two methods for ring enlargement of silacyclobutane into silacyclopentane have been described. (1) Treatment of 1-(1-iodoalkyl)silacyclobutane with t-BuOK or AgOAc provided 2-alkyl-1-silacyclopentanes which were easily converted into 1,4-diols by oxidative cleavage of carbon–silicon bond. (2) An addition of i-PrOLi to 1-[(Z)-1,2-epoxyhexyl]-1-methylsilacyclobutane gave erythro-2-(1-hydroxypentyl)-1-isopropoxy-1-methylsilacyclopentane, which was converted into (Z)-4-nonen-1-ol, (E)-4-nonen-1-ol, or 1,4,5-nonanetriol.
  The Chemical Society of Japan, English
  DOI：https://doi.org/10.1246/bcsj.68.250
  DOI ID：10.1246/bcsj.68.250, ISSN：0009-2673, CiNii Articles ID：130004148993
• STUDIES ON ORGANOSILICON CHEMISTRY .122. REACTION OF 2-OXIRANYLALLYLSILANES WITH ACETALS - DIRECT INTRODUCTION OF A VINYLOXIRANE MOIETY　　　　　　　　　　　　　　　
  M HOJO; N ISHIBASHI; K OHSUMI; K MIURA; A HOSOMI
  JOURNAL OF ORGANOMETALLIC CHEMISTRY, Volume：473, Number：1-2, First page：C1, Last page：C2, Jun. 1994
  Direct 2-oxiranylallylation to acetals can be attained using 2-oxiranyl-2-propenyltrimethylsilanes. These are a new type of nucleophiles incorporating a vinyloxirane moiety as an electrophilic functionality.
  ELSEVIER SCIENCE SA LAUSANNE, English
  ISSN：0022-328X, Web of Science ID：WOS:A1994NV19800043
• Introduction of Electrophiles to the α-Position of α,β-Unsaturated Aldehydes and Ketones by Sequential Conjugate Aminosilylation-Alkylation-Deamination　　　　　　　　　　　　　　　
  HOJO Makoto; NAGAYOSHI Masayuki; FUJII Atsuko; YANAGI Toshiharu; ISHIBASHI Naruyasu; MIURA Katsukiyo; HOSOMI Akira
  Chemistry Letters, Volume：1994, Number：4, First page：719, Last page：722, Apr. 1994
  Silylamines add to α,β-unsaturated aldehydes and ketones in 1,4-addition mode to generate amino-substituted silyl enol ethers without any catalysts. These easily isolable silyl enol ethers react with acetals and aldehydes in the presence of a Lewis acid to give α-alkoxyalkyl and α-hydroxyalkyl substituted α,β-unsaturated carbonyl compounds, respectively, after deamination by treatment with silica gel.
  The Chemical Society of Japan, English
  DOI：https://doi.org/10.1246/cl.1994.719
  DOI ID：10.1246/cl.1994.719, ISSN：0366-7022, CiNii Articles ID：10006890344, CiNii Books ID：AA00603318
• Tris(trimethylsilyl)silyl Radical Induced Bicyclization of 1,6-Dienes and 1,6-Enynes Providing 3,3-Bis(trimethylsilyl)-3-silabicyclo(3.3.0)octanes and 3-Silabicyclo(3.3.0)oct-1-enes.　　　　　　　　　　　　　　　
  Miura Katsukiyo; Oshima Koichiro; Utimoto Kiitiro
  Bull. Chem. Soc. Jpn., Volume：66, Number：8, First page：2348, Last page：2355, 1993
  Treatment of 1,6-dienes with tris(trimethylsilyl)silane in the presence of Et₃B or α,α′-azobis(isobutyronitrile) afforded 3,3-bis(trimethylsilyl)-3-silabicyclo[3.3.0]octanes in addition to monocyclized cyclopentanes. Bicyclization of 1,6-enynes provided the corresponding 3-silabicyclo[3.3.0]oct-1-enes.
  The Chemical Society of Japan, English
  DOI：https://doi.org/10.1246/bcsj.66.2348
  DOI ID：10.1246/bcsj.66.2348, ISSN：0009-2673, CiNii Articles ID：130004148319
• Triethylborane Induced Stereoselective Radical Addition of R3SiH to Acetylenes and Stereoselective Reduction of Alkenyl Iodides with Tris(trimethylsilyl)silane.　　　　　　　　　　　　　　　
  Miura Katsukiyo; Oshima Koichiro; Utimoto Kiitiro
  Bull. Chem. Soc. Jpn., Volume：66, Number：8, First page：2356, Last page：2364, 1993
  Triethylborane induced radical addition of various organosilanes (R₃SiH) to acetylenes has been studied. Among them, tris(trimethylsilyl)silane (TTMSS) proved to be the best reagent for the hydrosilylation of acetylenic compounds in terms of yield and stereoselectivity. For instance, reaction of 1-dodecyne with TTMSS at room temperature for 3 h under Et₃B catalyst provided (Z)-1-tris(trimethylsilyl)silyl-1-dodecene selectively in 98% yield. The stereochemical course of reduction of alkenyl iodides with TTMSS–Et₃B or n-Bu₃SnH–Et₃B has been examined. Treatment of 1-dimethylphenylsilyl-2-iodo-1-dodecene with TTMSS–Et₃B at room temperature afforded (Z)-1-dimethylphenylsilyl-1-dodecene selectively (Z/E > 30/1). On the other hand, treatment with n-Bu₃SnH-Et₃B gave (E)-1-dimethylphenylsilyl-1-dodecene exclusively.
  The Chemical Society of Japan, English
  DOI：https://doi.org/10.1246/bcsj.66.2356
  DOI ID：10.1246/bcsj.66.2356, ISSN：0009-2673, CiNii Articles ID：130004148344
• Tris(trimethylsilyl)silyl Radical Induced Bicyclization of 1,6-Dienes and 1,6-Enynes Providing 3,3-Bis(trimethylsilyl)-3-silabicyclo[3.3.0]octanes and 3-Silabicyclo[3.3.0]oct-1-enes　　　　　　　　　　　　　　　
  MIURA Katsukiyo; OSHIMA Koichiro; UTIMOTO Kiitiro
  Chemistry Letters, Volume：1992, Number：12, First page：2477, Last page：2478, Dec. 1992
  Treatment of 1,6-dienes with tris(trimethylsilyl)silane in the presence of triethylborane or AIBN afforded 3,3-bis(trimethylsilyl)-3-silabicyclo[3.3.0]octanes in addition to monocyclized cyclopentanes. Bicyclization of 1,6-enynes provided the corresponding 3-silabicyclo[3.3.0]oct-1-enes.
  The Chemical Society of Japan, English
  DOI：https://doi.org/10.1246/cl.1992.2477
  DOI ID：10.1246/cl.1992.2477, ISSN：0366-7022, CiNii Articles ID：10006880351, CiNii Books ID：AA00603318
• Triethylborane Induced Radical Reaction of Ketene Silyl Acetals with Polyhalomethanes.　　　　　　　　　　　　　　　
  Miura Katsukiyo; Sugimoto Jiro; Oshima Koichiro; Utimoto Kiitiro
  Bull. Chem. Soc. Jpn., Volume：65, Number：6, First page：1513, Last page：1521, 1992
  The treatment of ketene silyl acetal with tetrahalomethane or trihalomethane at room temperature in the presence of a catalytic amount of Et₃B provides 3,3-dihaloacrylate or (E)-3-haloacrylate, respectively. On the other hand, a reaction at −23 °C mainly gives 3,3,3-trihalopropanoate or 3,3-dihalopropanoate.
  The Chemical Society of Japan, English
  DOI：https://doi.org/10.1246/bcsj.65.1513
  DOI ID：10.1246/bcsj.65.1513, ISSN：0009-2673, CiNii Articles ID：130004147784
• Potassium t-butoxide or silver acetate induced ring enlargement of silacyclobutane into silacyclopentane. Application to the Synthesis of 1,4-Diol　　　　　　　　　　　　　　　
  Kozo Matsumoto; Katsukiyo Miura; Koichiro Oshima; Kiitiro Utimoto
  Tetrahedron Letters, Volume：32, Number：44, First page：6383, Last page：6386, Oct. 1991, [Reviewed]
  Treatment of 1-(1-iodoalkyl)-1-silacyclobutanes with t-BuOK or AgOAc provided 2-alkyl-1-silacyclopentanes which were easily converted into 1,4-diols by oxidative cleavage of carbonsilicon bonds. © 1991.
  English, Scientific journal
  DOI：https://doi.org/10.1016/0040-4039(91)80175-6
  DOI ID：10.1016/0040-4039(91)80175-6, ISSN：0040-4039, SCOPUS ID：0026050186
• Triethylborane Induced Perfluoroalkylation of Silyl Enol Ethers and Ketene Silyl Acetals with Perfluoroalkyl Iodides.　　　　　　　　　　　　　　　
  Miura Katsukiyo; Takeyama Yoshihiro; Oshima Koichiro; Utimoto Kiitiro
  Bull. Chem. Soc. Jpn., Volume：64, Number：5, First page：1542, Last page：1553, 1991
  Reaction of perfluoroalkyl iodides with silyl enol ethers mediated by Et₃B in the presence of base such as 2,6-dimethylpyridine provides mixtures of perfluoroalkylated trialkylsilyl enol ethers and α-perfluoroalkylated ketones. The yield and distribution of the products heavily depend on the nature of base employed. Treatment of a reaction mixture consisting of perfluoroalkylated silyl enol ether and α-perfluoroalkylated ketone with coned HCl in THF gives α-perfluoroalkylated ketone as a single product. Reaction of ketene silyl acetals with perfluoroalkyl iodides in the absence of base affords α-perfluoroalkylated esters in excellent yields.
  The Chemical Society of Japan, English
  DOI：https://doi.org/10.1246/bcsj.64.1542
  DOI ID：10.1246/bcsj.64.1542, ISSN：0009-2673, CiNii Articles ID：130001978860
• Rearrangement of 3-(trimethylsilylmethylthio)allyllithium.　　　　　　　　　　　　　　　
  Miura Katsukiyo; Oshima Koichiro; Utimoto Kiitiro
  Bull. Chem. Soc. Jpn., Volume：63, Number：9, First page：2584, Last page：2587, 1990
  Proton abstraction from 3-trimethylsilylmethylthio-1-propene by butyllithium followed by treatment with iodomethane provided 1-methylthio-4-trimethylsilyl-1-butene. Meanwhile, 1-trimethylsilylmethylthio-2-butene afforded 3-methyl-4-methylthio-1-trimethylsilyl-1-butene upon successive treatment with butyllithium and iodomethane.
  The Chemical Society of Japan, English
  DOI：https://doi.org/10.1246/bcsj.63.2584
  DOI ID：10.1246/bcsj.63.2584, ISSN：0009-2673, CiNii Articles ID：130001979369
• Synthesis and radical induced ring opening reaction of 1-trialkylsilyl-2-vinylcyclopropanes.　　　　　　　　　　　　　　　
  Miura Katsukiyo; Oshima Koichiro; Utimoto Kiitiro
  Bull. Chem. Soc. Jpn., Volume：63, Number：6, First page：1665, Last page：1677, 1990
  A variety of trialkylsilylvinylcyclopropanes were prepared by two different routes: (a) Cyclopropanation of 1-alkenylsilanes and (b) the reactions of 1-bromocyclopropyllithium with trimethylsilyl chloride. Radical induced ring opening reaction of these cyclopropanes were examined. 1-Dimethylphenylsilyl-2-vinylcyclopropane or 3-methyl-1-trialkylsilyl-2-vinylcyclopropane provided the corresponding homoallylic silane exclusively upon treatment with PhSH, Ph₃SnH, n-Bu₃SnH, or n-C₆F₁₃I. On the other hand, 2-phenyl-1-trimethylsilyl-3-vinylcyclopropane or 2-acetyl-1-trimethylsilyl-3-vinylcyclopropane gave allylic silane selectively.
  The Chemical Society of Japan, English
  DOI：https://doi.org/10.1246/bcsj.63.1665
  DOI ID：10.1246/bcsj.63.1665, ISSN：0009-2673, CiNii Articles ID：130001979654

• Development of Intramolecular C-C and C-Si Bond Forming Reactions Promoted by Diisobutylaluminum Hydride　　　　　　　　　　　　　　　
  Hidenori Kinoshita; Katsukiyo Miura
  JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, Volume：77, Number：1, First page：58, Last page：68, Jan. 2019
  Diisobutylaluminum hydride (DIBAL-H) is a common reagent in synthetic organic chemistry, and well known as a reducing agent of carbonyl groups and C-C multiple bonds. DIBAL-H is also used for modifications of alkynes. The preparation of haloalkenes via hydroalumination of alkynes and following halodemetallation of the resultant alkenylaluminums is the prime example. However, application of the alkenylaluminums to intramolecular bond formation remained largely unexplored. Recently, our attention has been focused on the reactivity and synthetic use of alpha-silylalkenylaluminums readly prepared from alkynylsilanes and DIBAL-H. During the course of our research, we succeeded in developing new cyclization reactions by DIBAL-H-promoted C-C and C-Si bond formation, which are valuable for regio-controlled syntheses of substituted benzenes, naphthalenes, indenes, benzosiloles, and siloles. These studies have provided not only efficient synthetic methods for carbocycles and silacycles but also novel information on the reactivity of organoaluminums.
  SOC SYNTHETIC ORGANIC CHEM JPN, Japanese, Book review
  DOI：https://doi.org/10.5059/yukigoseikyokaishi.77.58
  DOI ID：10.5059/yukigoseikyokaishi.77.58, ISSN：0037-9980, Web of Science ID：WOS:000461845700009
• 平成24-26年度日本学術振興会科学研究費補助金，挑戦的萌芽研究，研究成果最終報告書　　　　　　　　　　　　　　　
  2015
  新規炭素ラジカル発生法を基軸とする環境調和型有機合成法の開発
• 平成23-24年度旭硝子財団，研究奨励（第１分野），最終報告書　　　　　　　　　　　　　　　
  2013
  有機ケイ素化合物を利用する多置換ベンゼン類の高位置選択的合成
• Highly Regioselective Synthesis of Multisubstituted Benzenes Using Organosilicon Compounds
  三浦 勝清
  First page：1, Last page：5, 2013
  Japanese
  ISSN：1882-0069, CiNii Articles ID：40019976473
• 平成20-22年度日本学術振興会科学研究費補助金，基盤研究(C)，研究成果最終報告書　　　　　　　　　　　　　　　
  2011
  低毒性スズ反応剤の設計と創製に基づく環境調和型有機合成法の開発
• Development of new synthetic organic reactions using vinylsilanes and platinum catalysts　　　　　　　　　　　　　　　
  三浦勝清、木下英典
  CACS FORUM, Volume：2, Number：2, First page：2, Last page：5, 2011
  Vinylsilanes have frequently been used as carbon nucleophiles for efficient, stereospecific carbon-carbon bond formation. Their reactions occur usually at the position a to silicon. We herein report the Pt(II)-catalyzed nucleophilic addition of vinylsilanes at the b- or g-position leading to vinylation or allylation products, respectively. Under catalysis by PtCl2-2LiI, (Z)-vinylsilanes reacted with aromatic aldehydes at the position b to silicon, affording allyl silyl ethers in good to high yields. Use of MnI2 instead of LiI was effective in the vinylation of aliphatic aldehydes. We also succeeded in the one-pot vinylation of aldehydes with terminal alkynes and Et3SiH, in which PtCl2 successively catalyzed hydrosilylation of alkynes with Et3SiH and vinylation of aldehydes with the vinylsilanes formed. In contrast, under catalysis by PtCl2-2AgSbF6, the reaction of (Z)-vinylsilanes with dimethyl acetals proceeded at the g-position to give homoallylic ethers in good to high yields. When aldehydes and HC(OMe)3 were used instead of dimethyl acetals, the allylation products were obtained directly from aldehydes.
  Japanese
  CiNii Articles ID：40019204972, CiNii Books ID：AA12504266
• 平成２１年度科学研究費補助金実績報告書(研究実績報告書)特定領域研究「元素相乗系化合物の化学」　　　　　　　　　　　　　　　
  三浦勝清
  2010
  有機ケイ素化合物と白金触媒からなる元素相乗系の構築と精密有機合成への利用
  Japanese, Introduction scientific journal
• 平成２１年度科学研究費補助金実績報告書(研究実績報告書)基盤研究 (C)　　　　　　　　　　　　　　　
  三浦勝清
  2010
  低毒性スズ反応剤の設計と創製に基づく環境調和型有機合成法の開発
  Japanese, Introduction scientific journal
• 文部科学省科学研究費補助金 特定領域研究「元素相乗系化合物の化学」広報第九号 平成２１年度活動報告　　　　　　　　　　　　　　　
  三浦勝清
  2010
  有機１４族元素化合物と金属触媒からなる元素相乗系の構築と精密有機合成への利用
  Japanese, Introduction scientific journal
• Platinum(II)-catalyzed Acetal-Ene Reaction: Easy Access to Homoallylic Ethers　　　　　　　　　　　　　　　
  Katsukiyo Miura; Hiroyuki Izumi; Hidenori Kinoshita; Junji Ichikawa; Akira Hosomi
  CHEMISTRY LETTERS, Volume：38, Number：12, First page：1204, Last page：1205, Dec. 2009
  Catalytic use of PtCl2 and AgX (X = OTf and SbF6) has been found to effectively promote the intermolecular ene reaction of acetals and the tandem acetalization-ene reaction of aldehydes under solvent-free conditions.
  CHEMICAL SOC JAPAN, English
  DOI：https://doi.org/10.1246/cl.2009.1204
  DOI ID：10.1246/cl.2009.1204, ISSN：0366-7022, eISSN：1348-0715, CiNii Articles ID：10027176109, Web of Science ID：WOS:000273859200039
• Platinum-Catalyzed Nucleophilic Addition of Vinylsilanes at the beta-Position　　　　　　　　　　　　　　　
  Katsukiyo Miura; Gen Inoue; Hisashi Sasagawa; Hidenori Kinoshita; Junji Ichikawa; Akira Hosomi
  ORGANIC LETTERS, Volume：11, Number：21, First page：5066, Last page：5069, Nov. 2009
  In the presence of catalytic amounts of PtCl(2) and metal iodides, beta-substituted vinylsilanes reacted with aldehydes at the beta-position to give allyl silyl ethers. The Pt-catalyzed addition to aromatic aldehydes proceeded efficiently in the presence of Lil. The combined use of PtCl(2) and Mnl(2) was found to be effective in addition to aliphatic aldehydes.
  AMER CHEMICAL SOC, English
  DOI：https://doi.org/10.1021/ol902060r
  DOI ID：10.1021/ol902060r, ISSN：1523-7060, Web of Science ID：WOS:000271097100076
• Platinum-Catalyzed Nucleophilic Addition of Vinylsilanes at the beta-Position　　　　　　　　　　　　　　　
  Katsukiyo Miura; Gen Inoue; Hisashi Sasagawa; Hidenori Kinoshita; Junji Ichikawa; Akira Hosomi
  ORGANIC LETTERS, Volume：11, Number：21, First page：5066, Last page：5069, Nov. 2009
  In the presence of catalytic amounts of PtCl(2) and metal iodides, beta-substituted vinylsilanes reacted with aldehydes at the beta-position to give allyl silyl ethers. The Pt-catalyzed addition to aromatic aldehydes proceeded efficiently in the presence of Lil. The combined use of PtCl(2) and Mnl(2) was found to be effective in addition to aliphatic aldehydes.
  AMER CHEMICAL SOC, English
  DOI：https://doi.org/10.1021/ol902060r
  DOI ID：10.1021/ol902060r, ISSN：1523-7060, Web of Science ID：WOS:000271097100076
• Efficient Alkenation of Aldehydes and Ketones to alpha,beta-Unsaturated Esters Using alpha,alpha-Bis(dimethylsilyl)-substituted Esters　　　　　　　　　　　　　　　
  Katsukiyo Miura; Masaru Ebine; Kazunori Ootsuka; Junji Ichikawa; Akira Hosomi
  CHEMISTRY LETTERS, Volume：38, Number：8, First page：832, Last page：833, Aug. 2009
  alpha,alpha-Bis(dimethylsilyl)-substituted esters 1 were found to be quite valuable for alkenation of various aldehydes and ketones to alpha,beta-unsaturated esters. The reaction of aldehydes with 1 proceeded spontaneously in DMSO at 30 degrees C to give alpha,beta-unsaturated esters with good to high E selectivity. Under the same conditions, ketones were insensitive to 1; however, Li2SO4 and CaCl2 effectively accelerated their alkenation.
  CHEMICAL SOC JAPAN, English
  DOI：https://doi.org/10.1246/cl.2009.832
  DOI ID：10.1246/cl.2009.832, ISSN：0366-7022, eISSN：1348-0715, CiNii Articles ID：10025125236, Web of Science ID：WOS:000269899500037
• Efficient Alkenation of Aldehydes and Ketones to alpha,beta-Unsaturated Esters Using alpha,alpha-Bis(dimethylsilyl)-substituted Esters　　　　　　　　　　　　　　　
  Katsukiyo Miura; Masaru Ebine; Kazunori Ootsuka; Junji Ichikawa; Akira Hosomi
  CHEMISTRY LETTERS, Volume：38, Number：8, First page：832, Last page：833, Aug. 2009
  alpha,alpha-Bis(dimethylsilyl)-substituted esters 1 were found to be quite valuable for alkenation of various aldehydes and ketones to alpha,beta-unsaturated esters. The reaction of aldehydes with 1 proceeded spontaneously in DMSO at 30 degrees C to give alpha,beta-unsaturated esters with good to high E selectivity. Under the same conditions, ketones were insensitive to 1; however, Li2SO4 and CaCl2 effectively accelerated their alkenation.
  CHEMICAL SOC JAPAN, English
  DOI：https://doi.org/10.1246/cl.2009.832
  DOI ID：10.1246/cl.2009.832, ISSN：0366-7022, eISSN：1348-0715, CiNii Articles ID：10025125236, Web of Science ID：WOS:000269899500037
• 平成２０年度科学研究費補助金実績報告書（研究実績報告書）特定領域研究「炭素資源の高度分子変換」　　　　　　　　　　　　　　　
  2009
  ケイ素置換炭素小分子の設計・創製に基づく効率的有機合成法の開発
  Introduction scientific journal
• 平成２０年度科学研究費補助金実績報告書（研究実績報告書）特定領域研究「元素相乗系化合物の化学」　　　　　　　　　　　　　　　
  2009
  有機１４族元素化合物と金属触媒からなる元素相乗系の構築と精密有機合成への利用
  Introduction scientific journal
• 平成２０年度科学研究費補助金実績報告書（研究実績報告書）基盤研究 (C)　　　　　　　　　　　　　　　
  2009
  低毒性スズ反応剤の設計と創製に基づく環境調和型有機合成法の開発
  Introduction scientific journal
• 文部科学省科学研究費補助金 特定領域研究「炭素資源の高度分子変換」平成２０年度研究報告書　　　　　　　　　　　　　　　
  2009
  ケイ素置換炭素小分子の設計・創製に基づく効率的有機合成法の開発
  Introduction scientific journal
• 文部科学省科学研究費補助金 特定領域研究「元素相乗系化合物の化学」広報第七号 平成２０年度研究報告　　　　　　　　　　　　　　　
  2009
  有機１４族元素化合物と金属触媒からなる元素相乗系の構築と精密有機合成への利用
  Introduction scientific journal
• Platinum(II)-catalyzed annulation of 5-methyl-5-hexen-1-ols with aldehydes　　　　　　　　　　　　　　　
  Katsukiyo Miura; Makoto Horiike; Gen Inoue; Junji Ichikawa; Akira Hosomi
  CHEMISTRY LETTERS, Volume：37, Number：3, First page：270, Last page：271, Mar. 2008
  In the presence of catalytic amounts of PtCl2 and AgOTf, 5-methyl-5-hexen-1-ol reacted with aldehydes to give 2,3-disubstituted tetrahydropyrans in moderate to high yields with trans-stereoselectivity. Use of 5-methyl-5-hexen-1-ols bearing a methyl group at the C1-, C2-, or C3-position led to highly stereoselective synthesis of trisubstituted tetrahydropyrans.
  CHEMICAL SOC JAPAN, English
  DOI：https://doi.org/10.1246/cl.2008.270
  DOI ID：10.1246/cl.2008.270, ISSN：0366-7022, eISSN：1348-0715, CiNii Articles ID：10021078202, Web of Science ID：WOS:000255086600021
• Development of new synthetic organic reactions using stannyl radicals as key intermediates　　　　　　　　　　　　　　　
  Katsukiyo Miura; Akira Hosomi
  JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, Volume：66, Number：1, First page：17, Last page：27, Jan. 2008
  We herein review our studies on synthetic radical reactions using organotin compounds. The first section deals with homolytic allylstannylation of alkenes and alkynes, and the related reactions. In the presence of AIBN, certain allylstannanes react with electron-deficient alkenes and various alkynes to deliver both stannyl and allyl groups to the unsaturated bonds. This allylstannylation is tolerant to polar functionalities unlike a similar reaction catalyzed by a Lewis acid. In the second section, we introduce radical reactions of stannyl enolates. The enolates are valuable for alkylation of haloalkanes. The ability as radical transfer agent is successfully utilized for radical-based multi-component coupling and carbostannylation reactions. The third section describes highly regio- and stereoselective hydrostannylation of alkynols and alkenols with Lewis acidic hydrostannanes. The stereochemical control can be rationalized by intramolecular coordination of the hydroxy group to the Lewis acidic stannyl group in the beta-stannylated carbon radical intermediate.
  SOC SYNTHETIC ORGANIC CHEM JPN, Japanese, Book review
  ISSN：0037-9980, Web of Science ID：WOS:000252781600003
• スタンニルラジカルを鍵中間体とする新規有機合成反応の開発　　　　　　　　　　　　　　　
  三浦勝清、細見彰
  有機合成化学協会誌, Volume：66, Number：1, First page：17, Last page：27, 2008
  有機合成化学協会
  DOI：https://doi.org/10.5059/yukigoseikyokaishi.66.17
  DOI ID：10.5059/yukigoseikyokaishi.66.17
• Development of new synthetic organic reactions using stannyl radicals as key intermediates　　　　　　　　　　　　　　　
  Katsukiyo Miura; Akira Hosomi
  Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry, Volume：66, Number：1, First page：17, Last page：27, 2008
  We herein review our studies on synthetic radical reactions using organotin compounds. The first section deals with homolytic allylstannylation of alkenes and alkynes, and the related reactions. In the presence of AIBN, certain allylstannanes react with electron-deficient alkenes and various alkynes to deliver both stannyl and allyl groups to the unsaturated bonds. This allylstannylation is tolerant to polar functionalities unlike a similar reaction catalyzed by a Lewis acid. In the second section, we introduce radical reactions of stannyl enolates. The enolates are valuable for alkylation of haloalkanes. The ability as radical transfer agent is successfully utilized for radical-based multi-component coupling and carbostannylation reactions. The third section describes highly regio- and stereoselective hydrostannylation of alkynols and alkenols with Lewis acidic hydrostannanes. The stereochemical control can be rationalized by intramolecular coordination of the hydroxy group to the Lewis acidic stannyl group in the β-stannylated carbon radical intermediate.
  Society of Synthetic Organic Chemistry, Japanese
  DOI：https://doi.org/10.5059/yukigoseikyokaishi.66.17
  DOI ID：10.5059/yukigoseikyokaishi.66.17, ISSN：0037-9980, SCOPUS ID：42149131474
• Indium(III) acetate-catalyzed intermolecular radical addition of organic iodides to electron-deficient alkenes　　　　　　　　　　　　　　　
  Katsukiyo Miura; Mitsuru Tomita; Junji Ichikawa; Akira Hosomi
  ORGANIC LETTERS, Volume：10, Number：1, First page：133, Last page：136, Jan. 2008
  In the presence of phenylsilane and a catalytic amount of indium(III) acetate, organic iodides added to electron-deficient alkenes in ethanol at room temperature. Both simple and functionalized organic iodides were applicable to this reaction. A plausible reaction mechanism involves the formation of indium hydride species by hydride transfer from silicon to indium and an indium hydride-mediated radical chain process.
  AMER CHEMICAL SOC, English
  DOI：https://doi.org/10.1021/ol702712d
  DOI ID：10.1021/ol702712d, ISSN：1523-7060, CiNii Articles ID：80018009913, PubMed ID：18072784, Web of Science ID：WOS:000251929000034
• Platinum(H) salt catalyzed annulation of hydroxyalkyl-substituted vinylsilanes with aldehydes　　　　　　　　　　　　　　　
  K Miura; R Itaya; M Horiike; H Izumi; A Hosomi
  SYNLETT, Volume：(20), 3148-3150, Number：20, First page：3148, Last page：3150, Dec. 2005
  In the presence of catalytic amounts of PtCl2 and AgX (X = OTf or SbF6), (Z)-6-trimethylsilyl-5-hexen-1-ol and (Z)-5-trimethylsilyl-4-penten-1-ol reacted smoothly with aldehydes to give 2,3-disubstituted tetrahydropyrans and tetrahydrofurans, respectively, in good to high yields. The reaction mechanism involves the isomerization of the starting vinylsilanes to the corresponding allyl-silanes and subsequence Prins-type annulation with aldehydes.
  GEORG THIEME VERLAG KG, English
  DOI：https://doi.org/10.1055/s-2005-921926
  DOI ID：10.1055/s-2005-921926, ISSN：0936-5214, Web of Science ID：WOS:000235012400030
• Metal chloride-promoted aldol reaction of alpha-dimethylsilylesters with aldehydes, ketones, and alpha-enones　　　　　　　　　　　　　　　
  K Miura; T Nakagawa; A Hosomi
  SYNLETT, Volume：(12), 1917-1921, Number：12, First page：1917, Last page：1921, Aug. 2005
  In the presence of a catalytic amount of LiCl, alpha-dimethylsilylesters (alpha-DMS-esters) 1 smoothly reacted with various aldehydes at 30 degrees C to give aldols in good to high yields. On the other hand, the aldol reaction with ketones was effectively promoted by MgCl2 rather than by LiCl. alpha-Enones also underwent the metal chloride-promoted addition of 1 at the carbonyl carbon or beta-carbon.
  GEORG THIEME VERLAG KG, English
  DOI：https://doi.org/10.1055/s-2005-871938
  DOI ID：10.1055/s-2005-871938, ISSN：0936-5214, Web of Science ID：WOS:000231028100020
• Highly diastereoselective hydrostannylation of allyl and homoallyl alcohols with dibutyl(trifluoromethanesulfoxy)stannane　　　　　　　　　　　　　　　
  K Miura; D Wang; A Hosomi
  JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, Volume：127, Number：26, First page：9366, Last page：9367, Jul. 2005
  AMER CHEMICAL SOC, English
  DOI：https://doi.org/10.1021/ja052245n
  DOI ID：10.1021/ja052245n, ISSN：0002-7863, Web of Science ID：WOS:000230220900028
• Highly regio- and stereoselective hydrostannylation of alkynols with a new Lewis acidic hydrostannane　　　　　　　　　　　　　　　
  K Miura; D Wang; Y Matsumoto; A Hosomi
  ORGANIC LETTERS, Volume：7, Number：3, First page：503, Last page：505, Feb. 2005
  Bu2Sn(OTf)H (1a), easily prepared from Bu2SnH2 and TfOH, was found to be very valuable for highly regio- and stereoselective hydrostannylation of various propargyl alcohols leading to (Z)-gamma-stannylated allyl alcohols. The stannylation with la is applicable to the synthesis of hydroxysubstituted (Z)-vinylstannanes from terminal alkynes bearing a hydroxy group at the homoallylic or bishomoallylic position. The coordination of the hydroxy group to the Lewis acidic tin center plays an important role for the observed regio- and stereochemistry.
  AMER CHEMICAL SOC, English
  DOI：https://doi.org/10.1021/ol0474397
  DOI ID：10.1021/ol0474397, ISSN：1523-7060, Web of Science ID：WOS:000226679100037
• Highly regio- and stereoselective hydrostannylation of propargyl alcohols and ethers using dibutylchlorostannane and lithium chloride　　　　　　　　　　　　　　　
  K Miura; D Wang; A Hosomi
  SYNLETT, Volume：(3), 406-410, Number：3, First page：406, Last page：410, Feb. 2005
  In the presence of LiCl, dibutylehlorostannane (Bu2SnClH) reacted with gamma-unsubstituted propargyl alcohols and ethers to give gamma-stannylated allyl alcohols and ethers, respectively, with high regio- and stereoselectivity. These vinylstannane products could be successfully utilized for the Pd-catalyzed cross-coupling reaction.
  GEORG THIEME VERLAG KG, English
  DOI：https://doi.org/10.1055/s-2004-837219
  DOI ID：10.1055/s-2004-837219, ISSN：0936-5214, Web of Science ID：WOS:000227294800003
• Indium(III) acetate-catalyzed 1,4-reduction and reductive aldol reactions of alpha-enones with phenylsilane　　　　　　　　　　　　　　　
  K Miura; Y Yamada; M Tomita; A Hosomi
  SYNLETT, Volume：(11), 1985-1989, Number：11, First page：1985, Last page：1989, Sep. 2004
  A catalytic amount of In(OAc)(3) smoothly promoted 1,4-reduction of certain alpha-enones with PhSiH3 in ethanol at ambient temperature. The intermediary enolates could be used for inter- and intramolecular aldol reactions and intramolecular Michael addition.
  GEORG THIEME VERLAG KG, English
  DOI：https://doi.org/10.1055/s-2004-830862
  DOI ID：10.1055/s-2004-830862, ISSN：0936-5214, Web of Science ID：WOS:000223845200026
• Indium(III) chloride-promoted intramolecular addition of allylstannanes to alkynes　　　　　　　　　　　　　　　
  K Miura; N Fujisawa; A Hosomi
  JOURNAL OF ORGANIC CHEMISTRY, Volume：69, Number：7, First page：2427, Last page：2430, Apr. 2004
  In the presence of an equimolar amount of InCl3, 8-tributylstannyl-6-octen-1-ynes (allylstannanes bearing an alkynyl group) were efficiently cyclized to 2-allyl-1-methylenecyclopentanes. In contrast, catalytic use of InCl3 gave 2-allyl-1-(tributylstannylmethylene)cyclopentanes mainly by intramolecular allylstannylation. These cyclizations could proceed via intramolecular addition of an allylindium intermediate.
  AMER CHEMICAL SOC, English
  DOI：https://doi.org/10.1021/jo035780j
  DOI ID：10.1021/jo035780j, ISSN：0022-3263, Web of Science ID：WOS:000220506200029
• Regio- and stereoselective homolytic hydrostannylation of propargyl alcohols and ethers with dibutylchlorostannane　　　　　　　　　　　　　　　
  K Miura; D Wang; Y Matsumoto; N Fujisawa; A Hosomi
  JOURNAL OF ORGANIC CHEMISTRY, Volume：68, Number：22, First page：8730, Last page：8732, Oct. 2003
  The Et3B-initiated reaction of gamma-unsubstituted propargyl alcohols with dibutylchlorostannane (Bu2SnClH) at low temperature gave (Z)-vinylstannanes with high regio- and stereoselectivity. The corresponding alkyl propargyl ethers also underwent regio- and stereoselective homolytic hydrostannylation with Bu2SnClH; however, the regioselectivity was not so high as that with the propargyl alcohols.
  AMER CHEMICAL SOC, English
  DOI：https://doi.org/10.1021/jo035012s
  DOI ID：10.1021/jo035012s, ISSN：0022-3263, CiNii Articles ID：80016289165, PubMed ID：14575513, Web of Science ID：WOS:000186156700063
• 1,2-silyl-migrative cyclization of vinylsilanes bearing an amino group　　　　　　　　　　　　　　　
  K Miura; T Takahashi; T Hondo; A Hosomi
  CHIRALITY, Volume：15, Number：1, First page：41, Last page：52, Jan. 2003
  In the presence of an acid catalyst, alpha-alkyl-substituted (Z)-vinylsilanes 1, bearing a tosylamino group, were smoothly cyclized to trans-2-alkyl-3-silylpiperidines 2 (1,2-silyl-migration products) and (2R*, 1'S*)-2-(1'-silylalkyl)pyrrolidines 3. The elaboration of the reaction conditions enabled the selective preparation of each cyclized product. The acid-catalyzed cyclization of (Z)-vinylsilane 5, whose methylene tether is shorter than that of 1 by one carbon, formed only the 1,2-silyl-migration product 6 with high trans-selectivity. These cyclizations were found to proceed in a stereospecific manner. (C) 2002 Wiley-Liss, Inc.
  WILEY-LISS, English
  DOI：https://doi.org/10.1002/chir.10150
  DOI ID：10.1002/chir.10150, ISSN：0899-0042, Web of Science ID：WOS:000180030400009
• Acid-catalyzed Intramolecular Addition of a Hydroxy Group to Vinylgermanes　　　　　　　　　　　　　　　
  Miura Katsukiyo; Takahashi Tatsuyuki; Hosomi Akira
  Heterocycles, Volume：59, Number：1, First page：93, Last page：96, 01 Jan. 2003
  English
  ISSN：0385-5414, CiNii Articles ID：40005626773, CiNii Books ID：AA00663739
• 1,2-silyl-migrative cyclization of vinylsilanes bearing a hydroxy group: Stereoselective synthesis of multisubstituted tetrahydropyrans and tetrahydrofurans　　　　　　　　　　　　　　　
  K Miura; T Hondo; S Okajima; T Nakagawa; T Takahashi; A Hosomi
  JOURNAL OF ORGANIC CHEMISTRY, Volume：67, Number：17, First page：6082, Last page：6090, Aug. 2002
  Acid-catalyzed intramolecular addition of a hydroxy group to alpha-alkylated vinylsilanes has been studied. Treatment of (Z)-5-alkyl-5-silyl-4-penten-1-ols 1 (R = alkyl) with 5 mol % TiCl4 in CHCl3 gave trans-2-alkyl-3-silyltetrahydropyrans 2 exclusively (trans/cis = > 99/1 to 97/3). The cyclization efficiency and rate strongly depended on the geometry of the C-C double bond and the silyl group. The use of (E)-vinylsilanes resulted in lower yields with poor cis-selectivity. In the cyclization of (Z)-1 (R = Bu), the silyl group used, the reaction time, and the yield of 2 were as follows: SiMe2Ph, 9.5 h, 75%; SiMe3, 7.5 h, 66%; SiMePh2, 24 h, 58%; SiMe2-t-Bu, 0.75 h, 85%; SiMe2Bn, 1.5 h, 78%. This 1,2-silyl-migrative cyclization could be applied to stereoselective synthesis of trisubstituted tetrahydropyrans. The acid-catalyzed reaction of 1-, 2-, or 3-substituted (Z)-5-silyl-4-nonen-1-ols 8 gave r-2,t-3,c-6-, r-2,t-3,t-5-, or r-2,t-3,c-4-trisubstituted tetrahydropyrans with high diastereoselectivity, respectively. (Z)-4-Alkyl-4-silyl-3-buten-1-ols 5 as well as 1 underwent the 1,2-silylmigrative cyclization to give 2-alkyl-3-silyltetrahydrofurans 6 with high trans-selectivity. This silicon-directed cyclization was also available for the stereoselective synthesis of tri- and tetrasubstituted tetrahydrofurans.
  AMER CHEMICAL SOC, English
  DOI：https://doi.org/10.1021/jo026006j
  DOI ID：10.1021/jo026006j, ISSN：0022-3263, Web of Science ID：WOS:000177559800033
• Intramolecular Carbostannylation of Allyl- and Vinylstannanes via a Radical Chain Process　　　　　　　　　　　　　　　
  MIURA Katsukiyo; FUJISAWA Naoki; SAITO Hiroshi; NISHIKORI Hisashi; HOSOMI Akira
  Volume：2002, Number：1, First page：32, Last page：33, 05 Jan. 2002
  English
  ISSN：0366-7022, CiNii Articles ID：10009618506, CiNii Books ID：AA00603318
• Lewis base-promoted aldol reaction of dimethylsilyl enolates in aqueous dimethylformamide: Use of calcium chloride as a Lewis base catalyst　　　　　　　　　　　　　　　
  K Miura; T Nakagawa; A Hosomi
  JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, Volume：124, Number：4, First page：536, Last page：537, Jan. 2002
  AMER CHEMICAL SOC, English
  DOI：https://doi.org/10.1021/ja017218l
  DOI ID：10.1021/ja017218l, ISSN：0002-7863, Web of Science ID：WOS:000173456800012
• Homolytic carbostannylation of alkenes and alkynes with tributylstannyl enolates　　　　　　　　　　　　　　　
  K Miura; H Saito; N Fujisawa; D Wang; H Nishikori; A Hosomi
  ORGANIC LETTERS, Volume：3, Number：25, First page：4055, Last page：4057, Dec. 2001
  [GRAPHICS]
  In the presence of AIBN, tributylstannyl enolates derived from aromatic ketones reacted with electron-deficient alkenes; and a variety of alkynes to give the corresponding carbostannylated adducts. The reactions with methyl acrylate gave alpha -tributylstannylmethyl-gamma -ketoesters, unlike the known Michael-type reaction of stannyl enolates forming delta -ketoesters. The carbostannylation of alkynes proceeded in an anti addition mode to afford beta,gamma -unsaturated ketones. The reactivity of stannyl enolates as radical transfer agents could be utilized for radical cyclization of 1,6-enynes.
  AMER CHEMICAL SOC, English
  DOI：https://doi.org/10.1021/ol016797w
  DOI ID：10.1021/ol016797w, ISSN：1523-7060, Web of Science ID：WOS:000172602200019
• Acid-Catalyzed Cyclization of Vinylsilanes Bearing a Hemiacetal Group^1　　　　　　　　　　　　　　　
  MIURA Katsukiyo; TAKAHASHI Tatsuyuki; NISHIKORI Hisashi; HOSOMI Akira
  Volume：2001, Number：10, First page：958, Last page：959, 05 Oct. 2001
  English
  ISSN：0366-7022, CiNii Articles ID：10007770282, CiNii Books ID：AA00603318
• Allylstannylation of carbon-carbon and carbon-oxygen unsaturated bonds via a radical chain process　　　　　　　　　　　　　　　
  K Miura; H Saito; D Itoh; T Matsuda; N Fujisawa; D Wang; A Hosomi
  JOURNAL OF ORGANIC CHEMISTRY, Volume：66, Number：10, First page：3348, Last page：3355, May 2001
  In the presence of a radical initiator, allyltributylstannanes bearing an electron-withdrawing group at the beta -position smoothly reacted with electron-deficient terminal alkenes to give allylstannylated products in good yields. The stannyl group was introduced into the terminal carbon with high regioselectivity. The allylstannylation of homochiral 8-phenylmenthyl acrylate proceeded with moderate to good diastereoselectivity. Terminal and electron-deficient internal alkynes as well efficiently underwent the radical-initiated allylstannylation in an anti addition mode. The reaction of terminal alkynes showed the same regioselectivity as that of terminal alkenes. The present radical reaction was applicable to allylation of aromatic aldehydes and ketones.
  AMER CHEMICAL SOC, English
  DOI：https://doi.org/10.1021/jo0057295
  DOI ID：10.1021/jo0057295, ISSN：0022-3263, CiNii Articles ID：80012391054, PubMed ID：11348116, Web of Science ID：WOS:000168907700013
• Acid-catalyzed cyclization of vinylsilanes bearing a hydroxy group: A new method for stereoselective synthesis of disubstituted tetrahydrofurans　　　　　　　　　　　　　　　
  K Miura; S Okajima; T Hondo; T Nakagawa; T Takahashi; A Hosomi
  JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, Volume：122, Number：46, First page：11348, Last page：11357, Nov. 2000
  In the presence of a catalytic amount of TsOH or TiCl4, (Z)-5-silyl-4-penten-1-ols ((Z)-1) are smoothly cyclized to 2-silylmethyl-substituted tetrahydrofurans. This cyclization is applicable to the construction of a tetrahydropyran ring. The silyl group and the geometry of the C-C double bond strongly influence the cyclization rate. TBDMS and benzyldimethylsilyl groups considerably accelerate the cyclization in comparison with a dimethylphenylsilyl group, and (E)-vinylsilanes show much lower reactivity than the corresponding (Z)-isomers. The cyclization proceeds by stereospecific syn addition of the hydroxy group. Vinylsilanes 17, 19, and 21, (Z)-5-silyl-4-penten-1-ols bearing a substituent on the methylene tether, smoothly undergo the acid-catalyzed cyclization to give trans-2,5-, cis-2,4-, and trans-2,3-disubstituted tetrahydrofurans, respectively, with moderate to high stereoselectivity. The silyl group of some cyclized products can be easily converted into a hydroxy group with stereochemical retention.
  AMER CHEMICAL SOC, English
  DOI：https://doi.org/10.1021/ja002496q
  DOI ID：10.1021/ja002496q, ISSN：0002-7863, Web of Science ID：WOS:000165600300010
• Acid-catalyzed cyclization of vinylsilanes bearing a hydroxy group. Benzyldimethylsilyl group as an effective promoter and novel hydroxy surrogate　　　　　　　　　　　　　　　
  K Miura; T Hondo; T Takahashi; A Hosomi
  TETRAHEDRON LETTERS, Volume：41, Number：13, First page：2129, Last page：2132, Mar. 2000
  A benzyldimethylsilyl (BnDMS) group was found to effectively enhance the reactivity of vinylsilanes toward the acid-catalyzed intramolecular addition of a hydroxy group in comparison with a dimethylphenylsilyl group. The BnDMS group of the resultant cyclized products could be easily converted to a hydroxy group by the action of TBAF-H2O2-KHCO3. (C) 2000 Elsevier Science Ltd. All rights reserved.
  PERGAMON-ELSEVIER SCIENCE LTD, English
  DOI：https://doi.org/10.1016/S0040-4039(00)00091-5
  DOI ID：10.1016/S0040-4039(00)00091-5, ISSN：0040-4039, Web of Science ID：WOS:000086358400023
• Homolytic allylation of vinyl iodides with allylstannanes　　　　　　　　　　　　　　　
  K Miura; H Saito; D Itoh; A Hosomi
  TETRAHEDRON LETTERS, Volume：40, Number：50, First page：8841, Last page：8844, Dec. 1999
  In the presence of AIBN or Et3B, a variety of vinyl iodides reacted with allylstannanes bearing an electron-withdrawing group at the beta-position to afford 1,4-dienes in moderate to good yields. The allylation showed high stereoselectivity when the alpha-substituent of the iodides was a phenyl group, or the B-substituent was a bulky group. (C) 1999 Elsevier Science Ltd. All rights reserved.
  PERGAMON-ELSEVIER SCIENCE LTD, English
  DOI：https://doi.org/10.1016/S0040-4039(99)01856-0
  DOI ID：10.1016/S0040-4039(99)01856-0, ISSN：0040-4039, CiNii Articles ID：80010763850, Web of Science ID：WOS:000083827200029
• New Access to Cross-Coupling Reaction between Arylsilanes or Heteroarylsilanes and Aryl Halides Mediated by a Copper(I)Salt^1　　　　　　　　　　　　　　　
  ITO Hajime; SENSUI Hiro-omi; ARIMOTO Kikuo; MIURA Katsukiyo; HOSOMI Akira
  Chem. Lett., Volume：1997, Number：7, First page：639, Last page：640, Jul. 1997
  English
  ISSN：0366-7022, CiNii Articles ID：10002613054, CiNii Books ID：AA00603318
• Lewis acid-promoted addition of methylenecyclopropanes to aldehydes and ketones　　　　　　　　　　　　　　　
  K Miura; M Takasumi; T Hondo; H Saito; A Hosomi
  TETRAHEDRON LETTERS, Volume：38, Number：26, First page：4587, Last page：4590, Jun. 1997
  In the presence of TiCl4, methylenecyclopropane (1a) easily reacted with aliphatic aldehydes to give the beta-(chloromethyl)allylated products 2 in good yields along with a small amount of the methylenetetrahydrofurans 3. The reaction with chiral alpha- and beta-alkoxy aldehydes proceeded with high levels of chelation control. (C) 1997 Elsevier Science Ltd.
  PERGAMON-ELSEVIER SCIENCE LTD, English
  DOI：https://doi.org/10.1016/S0040-4039(97)00981-7
  DOI ID：10.1016/S0040-4039(97)00981-7, ISSN：0040-4039, CiNii Articles ID：80009696748, Web of Science ID：WOS:A1997XG71300019
• SILICON-DIRECTED CYCLIZATION OF VINYLSILANES BEARING HYDROXY GROUP CATALYZED BY AN ACID　　　　　　　　　　　　　　　
  K MIURA; S OKAJIMA; T HONDO; A HOSOMI
  TETRAHEDRON LETTERS, Volume：36, Number：9, First page：1483, Last page：1486, Feb. 1995
  Silicon-directed stereoselective syn addition of hydroxy group to olefinic double bond occurs intramolecularly in an acid-catalyzed cyclization of vinylsilanes bearing hydroxy group. Thus 5-dimethylphenylsilyl-4-penten-1-ol is smoothly cyclized to 2-(dimethylphenylsilyl)methyltetrahydrofuran upon the treatment of a catalytic amount of p-toluenesulfonic acid (TsOH) or TiCl4.
  PERGAMON-ELSEVIER SCIENCE LTD, English
  DOI：https://doi.org/10.1016/0040-4039(95)00065-K
  DOI ID：10.1016/0040-4039(95)00065-K, ISSN：0040-4039, Web of Science ID：WOS:A1995QK51800028

• 使える!有機合成反応実践ガイド　　　　　　　　　　　　　　　
  丸岡啓二、野崎京子、石井康敬、大寺純蔵、冨岡清、三浦勝清
  化学同人, 2010
  Total pages：504
• 三浦勝清、細見彰 Silicon Lewis Acids in New Acid Catalysis in Modern Organic Synthesis　　　　　　　　　　　　　　　
  2008
• 三浦勝清、細見彰 Silicon Lewis Acids in New Acid Catalysis in Modern Organic Synthesis　　　　　　　　　　　　　　　
  Wiley-VCH, 2008
• Silicon Lewis Acids in New Acid Catalysis in Modern Organic Synthesis　　　　　　　　　　　　　　　
  三浦勝清、細見彰
  Wiley-VCH, 2008, [Reviewed]
  Responsible for pages：48

• リン酸とヨウ化ナトリウムを用いる白金触媒によるアルキンのヒドロヨウ素化反応　　　　　　　　　　　　　　　
  柳沢萌華、木下英典、三浦勝清
  日本化学会第104春季年会 予稿集, Mar. 2024, [Domestic conference]
• 白金触媒によるアルキンの逆マルコフニコフ型ヒドロ塩素化反応：隣接官能基の効果　　　　　　　　　　　　　　　
  池島崇貴、三浦勝清、木下英典
  日本化学会第104春季年会 予稿集, Mar. 2024, [Domestic conference]
• 白金触媒によるアルキニルシランの水和二量化反応とアレーン合成への応用　　　　　　　　　　　　　　　
  安倍智夏、三浦勝清、木下英典
  日本化学会第104春季年会 予稿集, Mar. 2024, [Domestic conference]
• 有機アルミニウム試薬を用いるジヒドロシロール類の合成　　　　　　　　　　　　　　　
  大沢龍星、木下英典、三浦勝清
  第50回有機典型元素化学討論会 予稿集, Dec. 2023, [Domestic conference]
• 白金触媒とアルケニルシランを用いるアセタールのアルケニル化反応　　　　　　　　　　　　　　　
  服部桃磨、木下英典、三浦勝清
  第122回有機合成シンポジウム 予稿集, Jul. 2023, [Domestic conference]
• 白金触媒によるアルキニルシランの脱シリル化ヒドロ塩素化反応　　　　　　　　　　　　　　　
  田中健太、木下英典、三浦勝清
  第122回有機合成シンポジウム 予稿集, Jul. 2023, [Domestic conference]
• パラジウム触媒によるビニルエポキシド及びビニルアジリジンの 開環的シリル化とヘテロ環合成への応用　　　　　　　　　　　　　　　
  安齋活塁,木下英典,三浦勝清
  日本化学会第103春季年会予稿集, Mar. 2023, [Domestic conference]
• 官能性内部アルキンの位置及び立体選択的ヒドロ塩素化反応　　　　　　　　　　　　　　　
  福原寛,木下英典,三浦勝清
  第12回CSJ化学フェスタ2022予稿集, Oct. 2022, [Domestic conference]
• 白金触媒による末端アルキンの逆マルコフニコフ型ヒドロ臭素化反応　　　　　　　　　　　　　　　
  鈴木夢花,浅見晴香,木下英典,三浦勝清
  第12回CSJ化学フェスタ2022 予稿集, Oct. 2022, [Domestic conference]
• アルミニウム-リチウムジメタル中間体を経由す る多置換スタンノールとベンゾスタンノールの新規合 成法とその応用　　　　　　　　　　　　　　　
  黒川零,木下英典,三浦勝清
  68TH Symposium on Organometallic Chemistry, Japan ABSTRACTS, Sep. 2022, [Domestic conference]
• 水素化ジイソブチルアルミニウムを用いた縮環チオフェン類の合成　　　　　　　　　　　　　　　
  星野元太,木下英典,三浦勝清
  日本化学会第102春季年会予稿集, Mar. 2022, [Domestic conference]
• 水素化ジイソブチルアルミニウムを用いる1-ハロ-4-シリル-1,3-エンインからのシロール類のワンポット合成　　　　　　　　　　　　　　　
  風間洸洋,木下英典,三浦勝清
  日本化学会第102春季年会予稿集, Mar. 2022, [Domestic conference]
• パラジウム触媒を用いる置換フルベンの位置選択的合成　　　　　　　　　　　　　　　
  大木逸音,木下英典,三浦勝清
  日本化学会第102春季年会予稿集, Mar. 2022, [Domestic conference]
• アルケニルトリエチルシランと白金触媒を用いるアセタール類のアルケニル化反応　　　　　　　　　　　　　　　
  松田樹里,木下英典,三浦勝清
  日本化学会第102春季年会予稿集, Mar. 2022, [Domestic conference]
• イリジウム触媒とギ酸ナトリウムを用いる有機ハロゲン化物の還元反応　　　　　　　　　　　　　　　
  笠原美久,木下英典,三浦勝清
  第11回CSJ化学フェスタ2021予稿集, Oct. 2021, [Domestic conference]
• 白金触媒によるプロパルギル化合物の逆マルコフニコフ型ヒドロ塩素化反応　　　　　　　　　　　　　　　
  石田匠,木下英典,三浦勝清
  第10回JACI/GSCシンポジウム予稿集, Jun. 2021, [Domestic conference]
• 臭化水素を用いるアルキンの位置及び立体選択的なラジカル的ヒドロ臭素化　　　　　　　　　　　　　　　
  熊木渉,木下英典,三浦勝清
  第10回JACI/GSCシンポジウム予稿集, Jun. 2021, [Domestic conference]
• 多置換フルベンの合成とエレクトロクロミック特性　　　　　　　　　　　　　　　
  立村亮太,木下英典,三浦勝清
  第10回CSJ化学フェスタ2020予稿集, Oct. 2020, [Domestic conference]
• 末端アルキンに対する塩化水素の触媒的逆Markovnikov付加反応　　　　　　　　　　　　　　　
  西原弘樹,木下英典,三浦勝清
  第10回CSJ化学フェスタ2020予稿集, Oct. 2020, [Domestic conference]
• 水素化ジイソブチルアルミニウムを用いる多置換ゲルモールの合成　　　　　　　　　　　　　　　
  小嶋航,木下英典,三浦勝清
  第10回CSJ化学フェスタ2020予稿集, Oct. 2020, [Domestic conference]
• 白金触媒によるアルキニルシランの脱シリル化・ヒドロ塩素化反応　　　　　　　　　　　　　　　
  岩島健太,三浦勝清,木下英典
  第10回CSJ化学フェスタ2020予稿集, Oct. 2020, [Domestic conference]
• 塩化白金（II）を触媒とする内部アルキンのヒドロ塩素化反応　　　　　　　　　　　　　　　
  中島颯生,三浦勝清,木下英典
  第10回CSJ化学フェスタ2020予稿集, Oct. 2020, [Domestic conference]
• 末端アルキンに対する臭化水素のラジカル付加反応における立体選択性　　　　　　　　　　　　　　　
  熊木渉,三浦勝清,木下英典
  第10回CSJ化学フェスタ2020予稿集, Oct. 2020, [Domestic conference]
• Platinum-Catalyzed Nucleophilic Substitution of Acetals with Alkenylsilanes　　　　　　　　　　　　　　　
  櫻澤裕二,三浦勝清,木下英典
  日本化学会第100春季年会予稿集, Mar. 2020, [Domestic conference]
• 水素化ジイソブチルアルミニウムを用いる非対称多置換ゲルモールの合成　　　　　　　　　　　　　　　
  小嶋航,木下英典,三浦勝清
  日本化学会第100春季年会予稿集, Mar. 2020, [Domestic conference]
• Platinum-Catalyzed anti-Markovnikov Hydrochlorination of Terminal Alkynes　　　　　　　　　　　　　　　
  西原弘樹,三浦勝清,木下英典
  日本化学会第100春季年会予稿集, Mar. 2020, [Domestic conference]
• 白金触媒によるプロパルギルアルコール類の逆マルコフニコフ型ヒドロ塩素化反応　　　　　　　　　　　　　　　
  冨山亮太,三浦勝清,木下英典
  日本化学会第100春季年会予稿集, Mar. 2020, [Domestic conference]
• 白金触媒による内部アルキンに対するヒドロハロゲン化反応　　　　　　　　　　　　　　　
  中島颯生,三浦勝清,木下英典
  日本化学会第100春季年会予稿集, Mar. 2020, [Domestic conference]
• Platinum-Catalyzed anti-Markovnikov Hydrochlorination of Terminal Alkynes（白金触媒による末端アルキンの逆Markovnikov型ヒドロ塩素化反応）　　　　　　　　　　　　　　　
  西原弘樹,木下英典,三浦勝清
  66TH Symposium on Organometallic Chemistry, Japan ABSTRACTS, Sep. 2019, [Domestic conference]
• Diisobutylaluminum Hydride-Promoted Synthesis of Unsymmetrically Substituted Germoles　　　　　　　　　　　　　　　
  小嶋航,木下英典,三浦勝清
  ICCOC-GTL-16, ABSTRACT, Sep. 2019, [International conference]
• Platinum-catalyzed Alkenylation of Acetals and Aminals with Alkenylsilanes　　　　　　　　　　　　　　　
  猿舘孝生,木下英典,三浦勝清
  日本化学会第99春季年会予稿集, Mar. 2019, [Domestic conference]
• 水素化ジイソブチルアルミニウムを用いるベンゾチオフェンとベンゾチオフェンオキシドの選択的合成　　　　　　　　　　　　　　　
  内田誠也,木下英典,三浦勝清
  日本化学会第99春季年会予稿集, Mar. 2019, [Domestic conference]
• 1-アルケニル-2-エチニルベンゼンとアルミニウム試薬を用いる多置換ナフタレンのワンポット合成　　　　　　　　　　　　　　　
  野々山優真,木下英典,三浦勝清
  日本化学会第99春季年会予稿集, Mar. 2019, [Domestic conference]
• アリルシランを用いるアレーン類の分子内求電子的シリル化　　　　　　　　　　　　　　　
  福島亮太,木下英典,三浦勝清
  第8回CSJ化学フェスタ2018予稿集, Oct. 2018, [Domestic conference]
• 白金-銅触媒系によるアルキン類の水和二量化反応　　　　　　　　　　　　　　　
  田原裕輝,木下英典,三浦勝清
  日本化学会第98春季年会予稿集, Mar. 2018, [Domestic conference]
• 白金触媒を用いた末端アルキンに対するハロゲン化水素のアンチマルコフニコフ付加反応　　　　　　　　　　　　　　　
  山田瑞樹,木下英典,三浦勝清
  第7回CSJ化学フェスタ2017予稿集, Oct. 2017, [Domestic conference]
• 有機還元剤を用いる有機ハロゲン化物の触媒的ラジカル反応　　　　　　　　　　　　　　　
  真田かさね,木下英典,三浦勝清
  第7回CSJ化学フェスタ2017予稿集, Oct. 2017, [Domestic conference]
• Diisobutylaluminum Hydride-Promoted Intramolecular Silylation to Polysubstituted Siloles（水素化ジイソブチルアルミニウムを用いる分子内シリル化反応による多置換シロールの合成）　　　　　　　　　　　　　　　
  植田晃弘,木下英典,三浦勝清
  64TH Symposium on Organometallic Chemistry, Japan ABSTRACTS, Sep. 2017, [Domestic conference]
• Palladium-Catalyzed Cycloaddition of Trimethylsilylacetylene with Iodoarenes Leading to 1,3-Bis(trimethylsilyl)fulvenes（パラジウム触媒とヨードアレーン類を用いるトリメチルシリルアセチレンの環化付加反応による(1,3-ビストリメチルシリル)フルベン類の合成）　　　　　　　　　　　　　　　
  鈴木聡太,木下英典,三浦勝清
  64TH Symposium on Organometallic Chemistry, Japan ABSTRACTS, Sep. 2017, [Domestic conference]
• 水素化ジイソブチルアルミニウムを用いたベンゼン環構築法の開発と天然物合成への応用　　　　　　　　　　　　　　　
  矢口和樹,木下英典,三浦勝清
  日本化学会第97春季年会予稿集, Mar. 2017, [Domestic conference]
• 水素化ジイソブチルアルミニウムを用いた分子内炭素-ケイ素結合形成によるベンゾシロールおよびシロール類の合成　　　　　　　　　　　　　　　
  福本宏暉,植田晃弘,木下英典,三浦勝清
  日本化学会第97春季年会予稿集, Mar. 2017, [Domestic conference]
• Hydrative Dimerization of Alkynylsilanes to α,β-Unsaturated Ketones by PtCl2/CuCl/LiCl Catalyst System(白金-銅触媒系によるアルキニルシランのα,β-不飽和ケトンへの水和二量化反応)　　　　　　　　　　　　　　　
  田原裕輝,木下英典,三浦勝清
  63rd Symposium on Organometallic Chemistry, Japan ABSTRACTS, Sep. 2016, [Domestic conference]
• Diisobutylaluminum Hydride-Promoted Cyclization of o-[2-(Trimethylsilyl)ethynyl]styrenes to Substituted Naphthalenes(水素化ジイソブチルアルミニウムを用いたo-[2-(トリメチルシリル)エチニル]スチレン類の多置換ナフタレンへの環化反応)　　　　　　　　　　　　　　　
  矢口和樹,木下英典,三浦勝清
  63rd Symposium on Organometallic Chemistry, Japan ABSTRACTS, Sep. 2016, [Domestic conference]
• 水素化ジイソブチルアルミニウムを用いたインデン、ベンゾシロールおよび多置換シロールの合成　　　　　　　　　　　　　　　
  福本宏暉,植田晃弘,木下英典,三浦勝清
  第71回有機合成化学協会関東支部シンポジウム講演要旨集, May 2016, [Domestic conference]
• 水素化ジイソブチルアルミニウムを用いた多置換ナフタレン類の合成反応　　　　　　　　　　　　　　　
  矢口和樹,木下英典,三浦勝清
  第71回有機合成化学協会関東支部シンポジウム講演要旨集, May 2016, [Domestic conference]
• アリルシランをシリルカチオン前駆体として用いるアレーン類の分子内求電子的シリル化反応　　　　　　　　　　　　　　　
  市川顯二郎,木下英典,三浦勝清
  日本化学会第96春季年会予稿集, Mar. 2016, [Domestic conference]
• 水素化ジイソブチルアルミニウムを利用するシリル置換1,3-エンイン類の多置換シロールへの環化反応　　　　　　　　　　　　　　　
  植田晃弘,木下英典,三浦勝清
  日本化学会第96春季年会予稿集, Mar. 2016, [Domestic conference]
• パラジウム触媒とヘキサメチルジシランによるアルケニルエポキシドの開環的シリル化　　　　　　　　　　　　　　　
  太田和希,木下英典,三浦勝清
  日本化学会第95春季年会予稿集, Mar. 2015, [Domestic conference]
• ヒドロアルミニウム化を利用するシリル置換 1,3-ジエン-5-インの多置換ベンゼンへの環化反応　　　　　　　　　　　　　　　
  遠島隆行,木下英典,三浦勝清
  日本化学会第95春季年会予稿集, Mar. 2015, [Domestic conference]
• ヒドロアルミニウム化を利用するo-(シリルエチニル)スチレン類の置換ナフタレンへの環化反応　　　　　　　　　　　　　　　
  矢口和樹,木下英典,三浦勝清
  日本化学会第95春季年会予稿集, Mar. 2015, [Domestic conference]
• ヒドロアルミニウム化を利用するo-(シリルエチニル)ベンジルエーテル類の置換インデンへの環化反応　　　　　　　　　　　　　　　
  福本宏暉,木下英典,三浦勝清
  日本化学会第95春季年会予稿集, Mar. 2015, [Domestic conference]
• 三臭化インジウムと求電子剤を用いるアルキンとシリルエノラートの分子内反応　　　　　　　　　　　　　　　
  根岸研太,木下英典,三浦勝清
  日本化学会第95春季年会予稿集, Mar. 2015, [Domestic conference]
• 白金触媒とアルケニルシランを用いるアセタールのアルケニル化　　　　　　　　　　　　　　　
  福田大貴,木下英典,三浦勝清
  日本化学会第95春季年会予稿集, Mar. 2015, [Domestic conference]
• Hydroalumination-Triggered Cyclization of Silylated 1,3-Dien-5-ynes to Polysubstituted Benzenes　　　　　　　　　　　　　　　
  T. Tohjima, H. Kinoshita, and K. Miura
  XXVI International Conference on Organometallic Chemistry, Jul. 2014, [International conference]
• Diisobutylaluminum Hydride-Promoted Cyclization of Silylated Enynes: Efficient Synthesis of Indenes　　　　　　　　　　　　　　　
  H. Kinoshita, N. Hirai, and K. Miura
  XXVI International Conference on Organometallic Chemistry, Jul. 2014, [International conference]
• インジウム触媒とギ酸ナトリウムを用いるハロアルカンの還元反応　　　　　　　　　　　　　　　
  牧野洋平,木下英典,三浦勝清
  日本化学会第94春季年会, Mar. 2014, [Domestic conference]
• 白金触媒によるアルケニルシランの加アルコール分解　　　　　　　　　　　　　　　
  川村訓史,木下英典,三浦勝清
  日本化学会第94春季年会, Mar. 2014, [Domestic conference]
• 三臭化インジウムを触媒とするシリルエノラートのアルキンに対する分子内付加反応　　　　　　　　　　　　　　　
  根岸研太,木下英典,三浦勝清
  日本化学会第94春季年会, Mar. 2014, [Domestic conference]
• 白金触媒、アルキン、ヒドロシランを用いるアルデヒドのワンポット・アルケニル化　　　　　　　　　　　　　　　
  福田大貴,木下英典,三浦勝清
  日本化学会第94春季年会, Mar. 2014, [Domestic conference]
• 白金触媒によるアルキニルシランからα,β-不飽和ケトンへの水和二量化反応　　　　　　　　　　　　　　　
  菊地香澄美,木下英典,三浦勝清
  第60回有機金属化学討論会, Sep. 2013, [Domestic conference]
• 水素化ジイソブチルアルミニウムによるシリル置換1,3-ジエン-5-インの環化反応：多置換ベンゼンの位置選択的合成　　　　　　　　　　　　　　　
  遠島隆行,木下英典,三浦勝清
  第60回有機金属化学討論会, Sep. 2013, [Domestic conference]
• 水素化ジイソブチルアルミニウムを用いたシリル置換エンイン類の環化反応によるインデンおよびベンゾフルベンの効率的合成　　　　　　　　　　　　　　　
  平井信義,木下英典,三浦勝清
  第60回有機金属化学討論会, Sep. 2013, [Domestic conference]
• 白金触媒とアルケニルシランを用いる炭素求電子剤のワンポット-アリル化反応　　　　　　　　　　　　　　　
  木津亮介,木下英典,三浦勝清
  日本化学会第93春季年会, Mar. 2013, [Domestic conference]
• 白金触媒によるアルキニルシランの水和二量化反応: 反応の効率化と反応機構の検討　　　　　　　　　　　　　　　
  菊地香澄美,木下英典,三浦勝清
  日本化学会第93春季年会, Mar. 2013, [Domestic conference]
• シリル置換ジエンインのヒドロアルミニウム化と6π-電子環状反応を経る多置換ベンゼンの位置選択的合成　　　　　　　　　　　　　　　
  遠島隆行,木下英典,三浦勝清
  日本化学会第93春季年会, Mar. 2013, [Domestic conference]
• 水素化ジイソブチルアルミニウムを用いたシリル置換-1,3-エンイン類の交差反応による多置換ベンゼンの位置選択的合成　　　　　　　　　　　　　　　
  斉藤正浩,木下英典,三浦勝清
  日本化学会第93春季年会, Mar. 2013, [Domestic conference]
• 水素化ジイソブチルアルミニウムによるシリル置換エンイン類の環化反応：インデン及びベンゾフルベン類の効率的合成　　　　　　　　　　　　　　　
  平井信義,木下英典,三浦勝清
  日本化学会第93春季年会, Mar. 2013, [Domestic conference]
• パラジウム触媒とヘキサメチルジシランによるビニルシクロプロパンの開環的シリル化　　　　　　　　　　　　　　　
  菊池洋匡,木下英典,三浦勝清
  日本化学会第93春季年会, Mar. 2013, [Domestic conference]
• 1-ヨード-1-シリルアルケンと末端アルキンのパラジウム触媒反応を利用する多置換ベンゼンの位置選択的合成　　　　　　　　　　　　　　　
  高橋博俊,木下英典,三浦勝清
  日本化学会第93春季年会, Mar. 2013, [Domestic conference]
• α-ジメチルシリルニトリルのカルボニル化合物への求核付加反応　　　　　　　　　　　　　　　
  陣崎孝明,木下英典,三浦勝清
  有機金属化学討論会, Sep. 2012, [Domestic conference]
• ヨウ化アルケニルとアルキニルシランとのパラジウム触媒分子間反応によるシリル置換ベンゼン類の位置選択的合成　　　　　　　　　　　　　　　
  高橋博俊、木下英典,三浦勝清
  有機金属化学討論会, Sep. 2012, [Domestic conference]
• 水素化アルミニウムを用いるシリル置換1,3-エンインおよびアルキンからの四置換ベンゼンの位置選択的合成　　　　　　　　　　　　　　　
  木下英典,三浦勝清
  有機金属化学討論会, Sep. 2012, [Domestic conference]
• 白金触媒によるアルデヒドのワンポット-ビニル化とp-ベンゾキノンの添加効果　　　　　　　　　　　　　　　
  上村亮輔、木下英典、三浦勝清
  日本化学会第92春季年会(2012)講演予稿集, Mar. 2012, [Domestic conference]
• 白金触媒によるアルキニルシランの水和二量化反応　　　　　　　　　　　　　　　
  菊地香澄美、木下英典、三浦勝清
  日本化学会第92春季年会(2012)講演予稿集, Mar. 2012, [Domestic conference]
• 白金触媒とビニルシランを用いるアミナールのワンポット-アリル化反応　　　　　　　　　　　　　　　
  木津亮介、木下英典、三浦勝清
  日本化学会第92春季年会(2012)講演予稿集, Mar. 2012, [Domestic conference]
• 連続的カルボパラジウム化による多置換ベンゼン類の位置選択的合成　　　　　　　　　　　　　　　
  高橋博俊、木下英典、三浦勝清
  日本化学会第92春季年会(2012)講演予稿集, Mar. 2012, [Domestic conference]
• ジメチルシリルアセトニトリルの合成とカルボニル化合物へ付加反応　　　　　　　　　　　　　　　
  陣崎孝明、木下英典、三浦勝清
  日本化学会第92春季年会(2012)講演予稿集, Mar. 2012, [Domestic conference]
• トリベンジルスタンナンによるアルキン類のヒドロスタンニル化と有機合成への利用　　　　　　　　　　　　　　　
  山川健、木下英典、三浦勝清
  日本化学会第92春季年会(2012)講演予稿集, Mar. 2012, [Domestic conference]
• インジウム触媒、ヨードアルカン、ヒドロシランを用いる含窒素芳香族複素環のアルキル化　　　　　　　　　　　　　　　
  小川哲弥、木下英典、三浦勝清
  日本化学会第92春季年会(2012)講演予稿集, Mar. 2012, [Domestic conference]
• インジウムトリフラートを用いる5-ヘキシニルケトン類の環化反応　　　　　　　　　　　　　　　
  宮間千佳、木下英典、三浦勝清
  日本化学会第92春季年会(2012)講演予稿集, Mar. 2012, [Domestic conference]
• Platinum-Catalyzed Vinylation and Allylation of Carbon Electrophiles with Vinylsilanes　　　　　　　　　　　　　　　
  三浦勝清
  14th Asian Chemical Congress, Sep. 2011, [Invited], [International conference]
• インジウムトリフラートとトリフリルイミドを用いるアルキニルケトン類のConia型環化反応　　　　　　　　　　　　　　　
  宮間千佳、木下英典、三浦勝清
  第58回有機金属化学討論会, Sep. 2011, [Domestic conference]
• シリル置換1,3-エンイン類の骨格転位を経由する環化二量化：o,o-ビスシリルスチルベンの合成と光学的特性　　　　　　　　　　　　　　　
  木下英典、三浦勝清
  第58回有機金属化学討論会, Sep. 2011, [Domestic conference]
• 水素化ジイソブチルアルミニウムを用いるシリル置換1,3-エンイン類の骨格転位を伴う環化二量化　　　　　　　　　　　　　　　
  木下英典,三浦勝清
  日本化学会第91春季年会(2011)講演予稿集, Mar. 2011, [Domestic conference]
• インジウム触媒とハロアルカンを用いるピリジン類のアルキル化　　　　　　　　　　　　　　　
  小川哲弥、木下英典、三浦勝清
  日本化学会第91春季年会(2011)講演予稿集, Mar. 2011, [Domestic conference]
• トリベンジルスタンナンを用いるハロアルカンやアルキンのラジカル反応　　　　　　　　　　　　　　　
  山川健、木下英典、三浦勝清
  日本化学会第91春季年会(2011)講演予稿集, Mar. 2011, [Domestic conference]
• α-ジメチルシリル置換ニトリルを用いるカルボニル化合物のアルキル化とアルケン化　　　　　　　　　　　　　　　
  陣崎孝明、木下英典、三浦勝清
  日本化学会第91春季年会(2011)講演予稿集, Mar. 2011, [Domestic conference]
• 白金触媒を用いるワンポットでのアルキンのヒドロシリル化とアルデヒドのビニル化　　　　　　　　　　　　　　　
  上村亮輔、木下英典、三浦勝清
  日本化学会第91春季年会(2011)講演予稿集, Mar. 2011, [Domestic conference]
• 酸触媒を用いる5-ヘキシニルケトン類の環化反応　　　　　　　　　　　　　　　
  宮間千佳、山本清代美、木下英典、市川淳士、三浦勝清
  日本化学会第91春季年会(2011)講演予稿集, Mar. 2011, [Domestic conference]
• シリル置換1,3-エンイン類と水素化ジイソブチルアルミニウムを用いる四置換ベンゼン環の位置選択的合成　　　　　　　　　　　　　　　
  木下英典、石河智之、三浦勝清
  第57回有機金属化学討論会, Sep. 2010, [Domestic conference]
• 白金触媒,アルキン,ヒドロシランを用いるアルデヒドのワンポットビニル化反応　　　　　　　　　　　　　　　
  上村亮輔,木下英典,三浦勝清
  第57回有機金属化学討論会, Sep. 2010, [Domestic conference]
• 白金触媒とビニルシランを用いるアミナールのアリル化　　　　　　　　　　　　　　　
  堀越正裕,藤本真之,木下英典,市川淳士,三浦勝清
  日本化学会第90春季年会（2010）講演予稿集, Mar. 2010, [Domestic conference]
• 白金触媒、アルキン、ヒドロシランを用いるアルデヒドのワンポットビニル化反応　　　　　　　　　　　　　　　
  上村亮輔,木下英典,三浦勝清
  日本化学会第90春季年会（2010）講演予稿集, Mar. 2010, [Domestic conference]
• 酸触媒を用いるアルキニルケトンのConia反応　　　　　　　　　　　　　　　
  宮間千佳,山本清代美,木下英典,市川淳士,三浦勝清
  日本化学会第90春季年会（2010）講演予稿集, Mar. 2010, [Domestic conference]
• トリベンジルスズ化合物の合成と有機合成への利用　　　　　　　　　　　　　　　
  山川健,木下英典,三浦勝清
  日本化学会第90春季年会（2010）講演予稿集, Mar. 2010, [Domestic conference]
• アルデヒドおよびケトンに対するα-(ジメチルシリル)ニトリルの求核付加反応　　　　　　　　　　　　　　　
  荒川充,木下英典,市川淳士,三浦勝清
  日本化学会第90春季年会（2010）講演予稿集, Mar. 2010, [Domestic conference]
• Platinum(II)-Catalyzed Carbon?Carbon Bond-Forming Reactions with Vinylsilanes　　　　　　　　　　　　　　　
  三浦勝清
  特定研究領域「元素相乗系化合物の化学」第5回公開シンポジウム, Mar. 2010, [Domestic conference]
• Platinum-Catalyzed Allylation of Carbon Electrophiles with Vinylsilanes　　　　　　　　　　　　　　　
  2009
  Poster presentation
• Platinum(II)-Catalyzed Allylation of Acetals and Aminals with Vinylsilanes　　　　　　　　　　　　　　　
  2009
  Poster presentation
• Alkenation of Aldehydes and Ketones with α,α-Bis(dimethylsilyl)esters　　　　　　　　　　　　　　　
  2009
  Poster presentation
• インジウム触媒によるシリルエノラートとアルキンの分子内反応　　　　　　　　　　　　　　　
  三浦勝清,山本清代美,市川淳士,細見彰
  日本化学会第89春季年会（2009）講演予稿集, 2009, [Domestic conference]
• インジウム触媒とアリルスタンナンを用いる末端アルキンのアリル化　　　　　　　　　　　　　　　
  三浦勝清,伊藤啓佑,市川淳士,細見彰
  日本化学会第89春季年会（2009）講演予稿集, 2009, [Domestic conference]
• 白金触媒とビニルシランを用いるアルデヒドの連続的アセタール化-アリル化反応　　　　　　　　　　　　　　　
  三浦勝清,藤本真之,市川淳士,細見彰
  日本化学会第89春季年会（2009）講演予稿集, 2009, [Domestic conference]
• Platinum-Catalyzed Vinylation and Allylation of Carbon Electrophiles with Vinylsilanes　　　　　　　　　　　　　　　
  2009
• Platinum-Catalyzed Allylation of Carbon Electrophiles with Vinylsilanes　　　　　　　　　　　　　　　
  三浦勝清,藤本真之,堀越正裕、市川淳士,細見彰
  第56回有機金属化学討論会, 2009, [Domestic conference]
  Poster presentation
• Platinum(II)-Catalyzed Allylation of Acetals and Aminals with Vinylsilanes　　　　　　　　　　　　　　　
  三浦勝清,藤本真之,市川淳士,細見彰
  The 3rd International Symposium on Synergy of Elements, 2009, [International conference]
  Poster presentation
• Alkenation of Aldehydes and Ketones with α,α-Bis(dimethylsilyl)esters　　　　　　　　　　　　　　　
  三浦勝清、海老根大、大塚和則、市川淳士、細見彰
  The 15th IUPAC Symposium on Organometallic Chemistry Directed towards Organic Synthesis, 2009, [International conference]
  Poster presentation
• インジウム触媒によるシリルエノラートとアルキンの分子内反応　　　　　　　　　　　　　　　
  日本化学会第89春季年会（2009）講演予稿集, 2009
• インジウム触媒とアリルスタンナンを用いる末端アルキンのアリル化　　　　　　　　　　　　　　　
  日本化学会第89春季年会（2009）講演予稿集, 2009
• 白金触媒とビニルシランを用いるアルデヒドの連続的アセタール化-アリル化反応　　　　　　　　　　　　　　　
  日本化学会第89春季年会（2009）講演予稿集, 2009
• Platinum-Catalyzed Vinylation and Allylation of Carbon Electrophiles with Vinylsilanes　　　　　　　　　　　　　　　
  三浦勝清
  Second Japan-Singapore Bilateral Symposium on Catalysis, 2009, [International conference]
• Efficient Synthesis of α,β-Unsaturated Esters from Aldehydes and Ketones with α,α-Bis(dimethylsilyl)esters　　　　　　　　　　　　　　　
  2008
  Poster presentation
• 白金塩を触媒とするビニルシラン類の求核反応　　　　　　　　　　　　　　　
  三浦勝清
  平成20年度文部科学省科学研究費補助金特定領域研究「元素相乗系化合物の化学」第4回公開若手コロキウム, 2008, [Domestic conference]
• Platinum(II)-Catalyzed Nucleophilic Addition of Vinylsilanes at the β-Position　　　　　　　　　　　　　　　
  2008
  Poster presentation
• α,α-ビス（ジメチルシリル）エステルとカルボニル化合物との反応によるα,β-不飽和エステルの合成　　　　　　　　　　　　　　　
  三浦勝清、海老根大、市川淳士、細見彰
  日本化学会第88春季年会（2008）講演予稿集, 2008, [Domestic conference]
• ２価白金触媒を用いるビニルシランとアルデヒドの反応：適用範囲と反応機構の検討　　　　　　　　　　　　　　　
  三浦勝清、井上玄、市川淳士、細見彰
  日本化学会第88春季年会（2008）講演予稿集, 2008, [Domestic conference]
• Efficient Synthesis of α,β-Unsaturated Esters from Aldehydes and Ketones with α,α-Bis(dimethylsilyl)esters　　　　　　　　　　　　　　　
  三浦勝清、海老根大、市川淳士、細見彰
  第55回有機金属化学討論会, 2008, [Domestic conference]
  Poster presentation
• 白金塩を触媒とするビニルシラン類の求核反応　　　　　　　　　　　　　　　
  平成20年度文部科学省科学研究費補助金特定領域研究「元素相乗系化合物の化学」第4回公開若手コロキウム, 2008
• Platinum(II)-Catalyzed Nucleophilic Addition of Vinylsilanes at the β-Position　　　　　　　　　　　　　　　
  三浦勝清、井上玄、藤本真之、市川淳士、細見彰
  ICOMC2008, Book of Abstracts, 2008, [International conference]
  Poster presentation
• α,α-ビス（ジメチルシリル）エステルとカルボニル化合物との反応によるα,β-不飽和エステルの合成　　　　　　　　　　　　　　　
  日本化学会第88春季年会（2008）講演予稿集, 2008
• ２価白金触媒を用いるビニルシランとアルデヒドの反応：適用範囲と反応機構の検討　　　　　　　　　　　　　　　
  日本化学会第88春季年会（2008）講演予稿集, 2008

• Advanced Chemistry of Synthetic Organic Reactions, 講義
• Reading Circle on Molecular Chemistry IV, 講義
• Reading Circle on Molecular Chemistry III, 講義
• Reading Circle on Applied Chemistry, 講義
• Experiments in Applied Chemistry IV, 実習・実験
• Organic Chemistry II, 講義
• Synthetic Organic Chemistry I, 講義
• Organomolecular Engineering I, 講義
• Exercise of Organic Chemistry II, 演習
• Experiments in Applied Chemistry IV, 実習・実験
• Exercise of Organic Chemistry II, 演習
• Organomolecular Engineering II, 講義

• 2011
• 2011

• Sep. 2014, The Society of Silicon Chemistry, Japan
• Jan. 1998, American Chemical Society
• Jan. 1996, The Kinki Chemical Society, Japan
• Jan. 1994, The Society of Synthetic Organic Chemistry, Japan
• Jan. 1988, The Chemical Society of Japan

• Development of Green Methods for Organic Synthesis Based on New Reaction Systems for Carbon Radical Generation　　　　　　　　　　　　　　　
  Japan Society for the Promotion of Science, Grants-in-Aid for Scientific Research, Grant-in-Aid for Challenging Exploratory Research, 01 Apr. 2012 - 31 Mar. 2015
  MIURA Katsukiyo, Saitama University
  Grant amount(Total)：4030000, Direct funding：3100000, Indirect funding：930000
  Reactions of carbon radicals are valuable for fine organic synthesis. The reduction of organic halides with metal hydrides and low-valent metals has frequently been used for carbon radical generation. We herein report a new method for carbon radical generation from organic halides using sodium formate, a readily available, less toxic reductant. We found that the indium(III) salt-catalyzed reaction of organic halides with sodium formate in diethylene glycol diethyl ether gave dehalogenated products efficiently. Experimental results suggested that the present reduction should involve a radical mechanism. The radical cyclization of iodoalkynes by this catalytic system also proceeded successfully, and it demonstrated that the present method for carbon radical generation is useful for carbon-carbon bond formation.
  Grant number：24655074
• 有機ケイ素化合物を利用する多置換ベンゼン類の高位置選択的合成　　　　　　　　　　　　　　　
  旭硝子財団, 01 Apr. 2011 - 31 Mar. 2013
  三浦勝清
  Grant amount(Total)：2000000, Direct funding：2000000
• 低毒性スズ反応剤の設計と創製に基づく環境調和型有機合成法の開発　　　　　　　　　　　　　　　
  2008 - 2011
  Competitive research funding
• Development of Environmetally Friendly Organic Synthetic Methods by Design and Preparation of Less Toxic Organotin Reagents　　　　　　　　　　　　　　　
  Grant-in-Aid for Scientific Research, 2008 - 2011
  Development of easily decomposable organotin reagents is intended for environmenntally benign organic synthesis, easy purification process and new synthetic methods.
  Competitive research funding
• 有機14族元素化合物と金属触媒からなる元素相乗系の構築と精密有機合成への利用　　　　　　　　　　　　　　　
  文部科学省, 2006 - 2009
  三浦勝清
  Competitive research funding, Grant number：20036010
• Design of New Catalytic Systems Using Organosilicon and Organotin Reagents and Its Application to Fine Organic Synthesis　　　　　　　　　　　　　　　
  Grant-in-Aid for Scientific Research, 2006 - 2009
  Effective activaton of organosilicon and organotin compounds by metal catalysts has been studied for highly selective C-C bond formation.
  Competitive research funding
• ケイ素置換炭素小分子の設計・創製に基づく効率的有機合成法の開発　　　　　　　　　　　　　　　
  2005 - 2008
  三浦勝清
  Competitive research funding, Grant number：19020010
• Development of Efficient Synthetic Organic Reactions by Design and Preparation of Silicon-substituted Small Organic Molecules　　　　　　　　　　　　　　　
  Grant-in-Aid for Scientific Research, 2005 - 2008
  Organosilicon reagents bearing a dimethylsilyl group were designed and prepared for environmentally friendly organic synthesis.
  Competitive research funding
• 金属交換反応に基づく複合型元素化合物の創製と触媒的有機合成反応への利用　　　　　　　　　　　　　　　
  2007 - 2007
  三浦勝清
  Grant amount(Total)：2500000, Direct funding：2500000
  Grant number：19027010
• 白金およびインジウム触媒を利用する環境調和型有機合成法の開発　　　　　　　　　　　　　　　
  2005 - 2007
  Competitive research funding
• Development of Environmetally Friendly Organic Synthetic Methods Using Platinum and Indium Catalysts　　　　　　　　　　　　　　　
  Grant-in-Aid for Scientific Research, 2005 - 2007
  Platinum-catalyzed C-C bond forming reactions and indium-catalyzed radical reactions were developed.
  Competitive research funding
• ケイ素-炭素結合の活性化に基づく効率的分子変換法の開発　　　　　　　　　　　　　　　
  2006 - 2006
  三浦勝清
  Grant amount(Total)：2500000, Direct funding：2500000
  Grant number：18037007
• Organic Syntheses using Highly Reactive and Functional Organometallics　　　　　　　　　　　　　　　
  Japan Society for the Promotion of Science, Grants-in-Aid for Scientific Research, Grant-in-Aid for Scientific Research (B), 2004 - 2006
  HOSOMI Akira; HOJO Makoto; MIURA Katsukiyo, University of Tsukuba
  Grant amount(Total)：15600000, Direct funding：15600000
  1. Preparation of Dimethylsilyl-Protected Nucleophiles and Their Use for Organic Synthesis :
  Most of organosilicon reagents have a trimethylsilyl (TMS) group or a more bulky triorganosilyl group. Synthetic utility of silicon reagents bearing a less bulky silyl group has remained unexplored. We have found that dimethylsilyl (DMS)-protected nucleophiles are more reactive than TMS-protected nucleophiles. For example, in the presence of CaCl_2, ketone DMS enolates added smoothly to aldehydes at 30 ℃ in DMF to give aldols in high yield. In the reaction of DMS enolates, CaCl_2 would serve as Lewis base to activate the enolates by nucleophilic attack of the silicon by the chloride ion. DMS enolates are useful for the Mannich-type reaction of N-tosylimines and the Michael reaction of α-enones. Similarly, α-DMS-esters are more reactive than the corresponding TMS-based reagents. In the presence of metal chlorides (LiCl, MgCl_2, etc.), aldehydes and ketones underwent efficient aldol reactions of a-DMS-esters.
  We have developed the tandem aldol-reduction reaction of aldehydes with DMS enolates, which directly forms 1,3-diols stereoselectively. In this case, DMS enolates play two roles of carbon nucleophile and reductant. We have also demonstrated that DMS ethers and amines are valuable for reductive etherification and amination of carbonyls in the presence of a Lewis acid.
  2. Reduction and Carbon-Carbon Bond Formation under Catalysis by Indium Salts :
  We have found that PhSiH_3 reacts with haloalkanes in the presence of In(OAc)_3 to form the dehalogenated alkanes. This reduction would involve a radical chain mediated by indium hydride species. The PhSiH_3-In(OAc)_3 system is applicable to intermolecular radical addition of haloalkanes to electron-deficient alkenes. Additionally, it is valuable also for reductive aldol reaction of a-enones with aldehydes.
  We have succeeded in indium salt-promoted intramolecular addition of allylstannanes, allylsilanes, and silyl enolates to unactivated alkynes. The addition of allylstannanes proceeds probably by Sn-In transmetalation and subsequent allylindation, while the addition of allylsilanes and silyl enolates would involve electrophilic activation of the triple bond with the indium salts followed by nucleophilic addition of these silyl-protected nucleophiles. In the reaction of silyl enolates, the resultant vinylindium species can be used for further reaction with heteroatom and carbon electrophiles.
  Grant number：16350050
• Development of New Organosiiicon Reagents and Its Application to Environmentally Benign Organic Synthesis　　　　　　　　　　　　　　　
  Japan Society for the Promotion of Science, Grants-in-Aid for Scientific Research, Grant-in-Aid for Scientific Research (C), 2001 - 2003
  MIURA Katsukiyo; HOSOMI Akira, University of Tsukuba
  Grant amount(Total)：4100000, Direct funding：4100000
  1. Development of Synthetic Reagents Bearing a Dimethylsilyl Group and Its Application
  The aldol reaction of dimethylsilyl (DMS) enolates with aldehydes proceeded efficiently in the presence of alkali or alkali earth metal salts. As the result of reactions using various metal salts, it was found that metal chlorides show high activity and the reaction mechanism involves nucleophilic activation of silyl enolates. Interestingly, the aldol reaction proceeded even in the presence of water, and an aqueous solution of formaldehyde was usable. In the presence of magnesium chloride, DMS enolates reacted with α-mopes to give Michael adducts in good to high yields. Under similar conditions, DMS enolates also added to N-tosylimines. The Mannich-type reaction was effectively induced by the combined use of water and a catalytic amount of diisopropylamine. The base-catalyzed Mannich-type reaction showed high levels of diastereoselectivity. The aldol reactions of α-DMS-esters with aldehydes and ketones were effectively accelerated by alkali or alkali earth metal salts. The reaction with α-enones afforded aldol adducts in preference to Michael adducts. DMS ethers and DMS amines were found to be effective in the Lewis acid-catalyzed reductive etherification and amination of carbonyl compounds
  2. Radical Reactions Using Indium Catalysts and Hydrosilanes
  In the presence of a catalytic amount of indium(III) acetate, alkyl halides underwent reduction with phenylsilane to give alkanes in good yield. This reduction is tolerant to polar functionalities such as ether and ester groups. The reaction mechanism probably involves radical reduction with indium hydride species generated from indium(III) acetate and phenylsilane. The reduction system was applicable to an efficient intermolecular radical addition of alkyl halides to electron-deficient alkenes
  Grant number：13650910
• New Syntheses of Highly Reactive and Functional Organometallic Compounds and its Application to Organic Syntheses　　　　　　　　　　　　　　　
  Japan Society for the Promotion of Science, Grants-in-Aid for Scientific Research, Grant-in-Aid for Scientific Research (B), 2001 - 2003
  HOSOMI Akira; MIURA Katsukiyo, University of Tsukuba
  Grant amount(Total)：15100000, Direct funding：15100000
  The following results are obtained in this research project
  1.New Reactivity of a Reducing Reagent Generated from a Copper(I) Salt and a Hydrosilane : Selective Reduction of Ketones and Olefins Conjugated with an Aromatic Group
  Aromatic ketones and olefins were selectively converted to the corresponding alcohols and alkanes by a reagent prepared from a copper(I) salt and a hydrosilane. Excess use of the hydrosilane is most important to attain the high reactivities. One-electron transfer process as well as nucleophilic reaction of hydride would contribute the selectivity
  2.First Gold Complex-catalysed Selective Hydrosilylation of Organic Compounds
  The first example of the hydrosilylation of organic compounds such as aldehydes and an aldimine using a catalytic amount of a gold complex, which accomplished versatile regio-and chemoselective reduction of carbonyl compounds, is described
  3.Convenient Methods for Conjugate Silylation of α,β-Enones Using a Disilane Mediated by a Copper(I) Salt
  The β-Silylation of α,β-enones using disilanes smoothly proceeds with a stoichiometric and catalytic amount of a readily available copper(I) salt by easy manipulation. At elevated temperature, a stoichiometric amount of CuCl is effective for the silylation. In the presence of a silyl triflate, use of a catalytic amount of Cu_2O affords the product even at lower temperature. These procedures offer convenient tools for the synthesis of b-silylated ketones.
  4.New Method for Introduction of a Silyl Group into α,β-Enones Using a Disilane Catalyzed by a Copper(I) Salt
  This paper describes that the reaction of a disilane with a Cu(I) salt efficiently induces cleavage of the Si-Si bond cc generate a silyl nucleophile in an aprotic polar solvent and its 1,4-addition to a,(3-unsaturated enones smoothly proceed' with a catalytic amount of a Cu(I) salt. 1,1,2,2-Tetramethyl-l,2-diphenyldisilane reacts with (CuOTf)_2◇C_6H_6 to give 1,1,2,2-tetramethyl-1,2-diphenyldisiloxane at room temperature in DMI. In the presence of a,b-enones, the conjugate silylation smoothly proceeds to give the corresponding 3-silylated product in good yields (up to 100%) even with 5 mol% (10 mol% for Cu(I)) of (CuOTf)_2◇C_6H_6 and tributylphosphine (11 mol%) in DMF, DMI and diglyme. This reaction is successfully applied to hexamethyldisilane to generate a trimethylsilyl nucleophile, hitherto not easily accessible. A plausible reaction mechanism via the regeneration of CuOTf in a catalytic cycle is proposed
  5.Boration of an α,β-enone using a diboron promoted by a copper(I)-phosphine mixture catalyst
  The Cu(I)-catalyzed boration of an a,(3-enone using a diboron is described. Combination of a Cu(I) salt and tributylphosphine is an effective catalyst system, though the individual use of Cu(I) and tributylphosphine is not active far the reaction
  6.An Unprecedented Catalytic Reaction Using Gold(I) Complexes
  This paper describes that Au complexes efficiently catalyze dehydrogenative dimerization of trialkylstannanes and its catalytic activity is extensively high (0.1 mol%, 48 h) as comparable to the Pd catalysts
  Grant number：13450362
• 11族金属錯体を用いた新規触媒反応の設計と有機合成反応の探索　　　　　　　　　　　　　　　
  2000 - 2001
  Grant amount(Total)：1800000, Direct funding：1800000
  Grant number：12875174
• New Syntheses of Highly Reactive and Functional Organometallic Compounds and its Application to Organic Syntheses　　　　　　　　　　　　　　　
  Japan Society for the Promotion of Science, Grants-in-Aid for Scientific Research, Grant-in-Aid for Scientific Research (B), 1999 - 2001
  HOSOMI Akira; ITO Hajime; MIURA Katsukiyo; HOJO Makoto; TOMINAGA Yoshiori; TATEIWA Jun-ichi, University of Tsukuba
  Grant amount(Total)：14100000, Direct funding：14100000
  The following results are obtained in this research project.
  Acid-Catalyzed Cyclization ofVinylsilanes Bearing an Amino Group. Stereoselective Synthesis ofPyrrolidines
  In the presence of an acid catalyst, vinylsilanes bearing an amino group protected by an electron-withdrawing group were smoothly bychzed to 2-(silylmethyl) pyrrolidines. This cyclization was utilized for the Stereoselective synthesis of 2 ndisubstituted pyrrqlidines (n = 3-5).
  Radical Cyclization of 1-6-Enynes Using Allylstannanes and New Radical Reactions Using Stannyl Enolates as Radical Transfer Agents
  In the presence of AEBN, allyltributylstannanes bearing a radical-stabilizing group at the β-position smoothly reacted with 1,6-enynes to give cyclized products incorporated with the stannyl and allyl groups in moderate to good yields This cyclization is valuable for the synthesis of highly functionalized 5-membered carbocycles and heterocycles The reactions with β-cyanoallylstannane formed a certain amount of bicyclo[4.3.0]non-l-enes along with monocyclized products. The radicaHmtiated reactions of α-halo-esters, -nitriles, and -ketones with stannyl enolates gave the corresponding γ-keto denvatives in moderate to high yields. This homolytic process was applied to the three-component coupling reaction among stannyl enolates, haloalkanes, and electron-deficient alkenes.
  Silicon-directed Cyclization of Vinylysilanes : Stereoselective Synthesis of Tetrahydrofurans and Tetrahydropyrans
  Silicon-directed Stereoselective syn addition of hydroxy group to olefmic double bond occurs intramolecularly in an acid-catalyzed cyclization of vinylsilanes bearing hydroxy group. The cyclization proceeds by stereospecific syn addition of the hydroxy group Vinylsilanes, (Z)-5-silyl-4-penten-l-ols bearing a substituent on the methylene tether, smoothly undergo the acid-catalyzed cyclization to give trans-2,5-, cis-2,4-, and trans-2,3-disubstituted tetrahydrofurans respectively, with moderate to high stereoselectivitv.
  Manganese Ate Species: Generation,and Reactions with Electrophiles
  Trialkylmanganese (II) ate reagents, "RMnLi" reacted with iodomethylsulfides to produce thiomethylmanganese reagents, where the manganate serves as a reductant not an alkylation agent. The reductive behavior of trialkylmanganese (II) ate reagents provides a protocol for the direct generation of a new class of reagents thiomethylmanganese reagents with structural variety, and the generated thiomethylmanganese reagents reacted with allyl bromides, enones and aldehydes.
  New Method for Introduction of a Silyl Group into α,β-Enones Using a Disilane Catalyzed by a Copper(I) salt.
  The reaction of a disilane with a Cu(I) salt efficiently induces cleavage of the Si-Si bond to generate a silyl nucleophile in aprotic polar solvent and its 1,4-addition to α,β-unsaturated enones smoothly proceeds with a catalytic amount of a Cu(I) salt were found. This reaction is successfully applied to hexamethyldisilane to generate a trimethylsilyl nucleophile hitherto not easily accessible.
  Unprecedented Manganese-Mediated Reactions : Generation of Non-Stabilized Carbonyl Ylids.
  Activated manganese generates nonstabilized carbonyl ylides from bis (chloromethyl) ethers as a precursor, and using this system with manganese as a reductant, the reactions of the ylides with electron-deficient dipolarophiles can be attained without the direct reduction of dipolarophiles by the reductant.
  Grant number：11554029
• New Syntheses of Highly Reactive and Functional Organometallic Compounds and its Application to Organic Syntheses　　　　　　　　　　　　　　　
  Japan Society for the Promotion of Science, Grants-in-Aid for Scientific Research, Grant-in-Aid for Scientific Research (B)., 1998 - 2000
  HOSOMI Akira; ITO Hajime; MIURA Katsukiyo; HOJO Makoto; TATEIWA Jun-ichi, University of Tsukuba
  Grant amount(Total)：14200000, Direct funding：14200000
  The following results are obtained in this research project.
  1. Silicon-directed Cyclization of Vinylysilanes : Stereoselective Synthesis of Tetrahydrofurans and Tetrahydropyrans
  Silicon-directed stereoselective syn addition of hydroxy group to olefinic double bond occurs intramolecularly in an acid-catalyzed cyclization of vinylsilanes bearing hydroxy group. The cyclization proceeds by stereospecific syn addition of the hydroxy group. Vinylsilanes, (Z)-5-silyl-4-penten-1-ols bearing a substituent on the methylene tether, smoothly undergo the acid-catalyzed cyclization to give trans-2,5-, cis-2,4-, and trans-2,3-disubstituted tetrahydrofurans, respectively, with moderate to high stereoselectivity.
  2. Acid-Catalyzed Cyclization of Vinylsilanes Bearing an Amino Group. Stereoselective Synthesis of Pyrrolidines
  In the presence of an acid catalyst, vinylsilanes bearing an amino group protected by an electron-withdrawing group were smoothly cyclized to 2-(silylmethyl) pyrrolidines. This cyclization was utilized for the stereoselective synthesis of 2, n-disubstituted pyrrolidines (n=3-5).
  3. Unprecedented Manganese-Mediated Reactions : Generation of Non-Stabilized Carbonyl Ylids
  Activated manganese generates nonstabilized carbonyl ylides from bis (chloromethyl) ethers as a precursor, and using this system with manganese as a reductant, the reactions of the ylides with electron-deficient dipolarophiles can be attained without the direct reduction of dipolarophiles by the reductant.
  4. Manganese Ate Species : Generation and Reactions with Electrophiles
  Trialkylmanganese (II) ate reagents, "R_3MnLi" reacted with iodomethylsulfides to produce thiomethylmanganese reagents, where the manganate serves as a reductant not an alkylation agent.
  The reductive behavior of trialkylmanganese (II) ate reagents provides aprotocol for the direct generation of a new class of reagents, thiomethylmanganese reagents with structural variety, and the generated thiomethylmanganese reagents reacted with allyl bromides, enones and aldehydes.
  5. Radical Cyclization of 1,6-Enynes Using Allylstannanes and New Radical Reactions Using Stannyl Enolates as Radical Transfer Agents
  In the presence of AIBN, allyltributylstannanes bearing a radical-stabilizing group at the β-position smoothly reacted with 1,6-enynes to give cyclized products incorporated with the stannyl and allyl groups in moderate to good yields. This cyclization is valuable for the synthesis of highly functionalized 5-membered carbocycles and heterocycles. The reactions with β-cyanoallylstannane formed a certain amount of bicyclo [4.3.0] non-1-enes along with monocyclized products. The radical-initiated reactions of α-halo-esters, -nitriles, and -ketones with stannyl enolates gave the corresponding γ-keto derivatives in moderate to high yields. This homolytic process was applied to the three-component coupling reaction among stannyl enolates, haloalkanes, and electron-deficient alkenes.
  6. New Method for Introduction of a Silyl Group into α, β-Enones Using a Disilane Catalyzed by a Copper (I) salt.
  The reaction of a disilane with a Cu (I) salt efficiently induces cleavage of the Si-Si bond to generate a silyl nucleophile in an aprotic polar solvent and its 1,4-addition to α, β-unsaturated enones smoothly proceeds with a catalytic amount of a Cu (I) salt were found. This reaction is successfully applied to hexamethyldisilane to generate a trimethylsilyl nucleophile, hitherto not easily accessible.
  Grant number：10450334
• New Generation of Reactive 1,3-Dipole and Radical Reagents and Dynamic Sterocontrol　　　　　　　　　　　　　　　
  Japan Society for the Promotion of Science, Grants-in-Aid for Scientific Research, Grant-in-Aid for Scientific Research on Priority Areas (B), 1998 - 2000
  HOSOMI Akira; OKU Akira; MIURA Katsukiyo; HOJO Makoto; NAOTA Ken; IWASAWA Shinji, University of Tsukuba
  Grant amount(Total)：55700000, Direct funding：55700000
  1. Silicon-directed Cyclization of Vinylysilanes : Stereoselective Synthesis of Tetrahydrofurans and Tetrahydropyrans
  Silicon-directed stereoselective syn addition of hydroxy group to olefinic double bond occurs intramolecularly in an acid-catalyzed cyclization of vinylsilanes bearing hydroxy group. The cyclization proceeds by stereospecific syn addition of the hydroxy group. Vinylsilanes, (Z)-5-silyl-4-penten-1-ols bearing a substituent on the methylene tether, smoothly undergo the acid-catalyzed cyclization to give trans-2,5-, cis-2,4-, and trans-2,3-disubstituted tetrahydrofurans, respectively, with moderate to high stereoselectivity.
  2. Acid-Catalyzed Cyclization of Vinylsilanes Bearing an Amino Group. Stereoselective Synthesis of Pyrrolidines
  In the presence of an acid catalyst, vinylsilanes bearing an amino group protected by an electron-withdrawing group were smoothly cyclized to 2-(silylmethyl)pyrrolidines. This cyclization was utilized for the stereoselective synthesis of 2,n-disubstituted pyrrolidines (n=3-5).
  3. Unprecedented Manganese-Mediated Reactions : Generation of Non-Stabilized Carbonyl Ylids
  Activated manganese generates nonstabilized carbonyl ylides from bis(chloromethyl) ethers as a precursor, and using this system with manganese as a reductant, the reactions of the ylides with electron-deficient dipolarophiles can be attained without the direct reduction of dipolarophiles by the reductant.
  4. Manganese Ate Species : Generation and Reactions with Electrophiles
  Trialkylmanganese(II) ate reagents, "R_3MnLi" reacted with iodomethylsulfides to produce thiomethylmanganese reagents, where the manganate serves as a reductant not an alkylation agent. The reductive behavior of trialkylmanganese(II) ate reagents provides a protocol for the direct generation of a new class of reagents, thiomethylmanganese reagents with structural variety, and the generated thiomethylmanganese reagents reacted with allyl bromides, enones and aldehydes.
  5. Radical Cyclization of 1,6-Enynes Using Allylstannanes and New Radical Reactions Using Stannyl Enolates as Radical Transfer Agents
  6. New Method for Introduction of a Silyl Group into α,β-Enones Using a Disilane Catalyzed by a Copper(I) salt.
  The reaction of a disilane with a Cu(I) salt efficiently induces cleavage of the Si-Si bond to generate a silyl nucleophile in an aprotic polar solvent and its 1,4-addition to α,β-unsaturated enones smoothly proceeds with a catalytic amount of a Cu(I) salt were found. This reaction is successfully applied to hexamethyldisilane to generate a trimethylsilyl nucleophile, hitherto not easily accessible.
  7. The first systematic studies on the structure and reactivities of C-and N-bound isomers of transition metal a-cyanocarbanions have been carried out. Strong contribution of stereochemistry of ligands to their reactivities and catalysis has been clarified in view of structural analysis, organometallic transformations, and mechanistic investigations
  8. Dynamic control of the reaction pathways in the pentacarbonyltungsten catalyzed cyclization of ω-acetylenic silyl enol ethers is achieved giving either exo or endo cyclized product selectively by the appropriate choice of the reaction conditions.
  Grant number：10208203
• 高配位遷移金属化合物の新規生成と関連化合物を用いる新反応の開発　　　　　　　　　　　　　　　
  1998 - 1999
  Grant amount(Total)：1800000, Direct funding：1800000
  Grant number：10874106
• マンガンアート錯体および関連有機金属化合物を用いる新反応の展開　　　　　　　　　　　　　　　
  1997 - 1997
  Grant amount(Total)：2100000, Direct funding：2100000
  Grant number：09875224
• 実践的有機金属反応剤の開発と天然物指向有機合成への新展開　　　　　　　　　　　　　　　
  1997 - 1997
  Grant amount(Total)：2200000, Direct funding：2200000
  Grant number：09231206
• 高配位構造を有する金属活性種と高次触媒体の構築に関する合成化学研究　　　　　　　　　　　　　　　
  1997 - 1997
  Grant amount(Total)：1600000, Direct funding：1600000
  Grant number：09218209
• New Reactions Using Highly Functional Organometallic Compounds and its Application to Synthetic Chemistry　　　　　　　　　　　　　　　
  Japan Society for the Promotion of Science, Grants-in-Aid for Scientific Research, Grant-in-Aid for Scientific Research (B), 1996 - 1997
  HOSOMI Akira; ITO Hajime; MIURA Katsukiyo; HOJO Makoto, University of Tsukuba
  Grant amount(Total)：7900000, Direct funding：7900000
  The following results are obtained in this research project.
  1.Silicon-directed Cyclization of Vinylysilanes : Stereoselective Synthesis of Tetrahydrofuranes and Tetrahydropyranes
  Silicon-directed stereoselective syn addition of hydroxy group to olefinic double bond occurs intramolecularly in an acid-catalyzed cyclization of vinylsilanes bearing hydroxy group. Thus 5-dimethylphenylsilyl-4-penten-1-ol is smoothly cyclized to 2- (dimethylphenylsilyl) methyltetrahydrofuran upon the treatment of a catalytic amount of p-toluenesulfonic acid (TsOH) or TiCl_4.
  2.Unprecedented Samarium-Mediated Reactions : Generation of Non-Stabilized Carbonyl Ylids
  Samarium reveals a strong reducing ability and by virtue of this character together with its oxophilicity, is widely applied to organic synthesis in the formation of carbon-carbon bonds and transformation of a variety of functionalities with high selectivities. In the course of our study on the generation and reactions of reactive species, we report herein the generation of novel active species, non-stabilized carbonyl ylids from iodomethyl silyl ethers mediated by samarium, otherwise inaccessible, and their [3+2] cycloadditions to a variety of unsaturated compounds such as aldehydes, alkenes, allenes, and alkynes.
  3.Manganese AteSpecies : Generation and Reactions with Electrophiles
  Tetrabutylmanganese ate complex 'Bu_4MnLi_2' reacts with allylic and prop-2-ynylic bromides to generate the corresponding allyl-and prop-2-ynyl-manganese species which further react with electrophiles such as aldehydes, ketones, epoxide, and chlorosilanes to afford the corresponding allylated and prop-2-ynylated and/or allenylated products in high yields.
  4.Allylstannylation of Alkynes and Alkenes via a Radical Process : Stereoselective Synthesis of Di-and Tri-Substituted Vinylstannanes
  In the presence of AIBN,allylstannanes bearing an electron-withdrawing group at the beta-position easily reacted with terminal and electron-deficient internal alkynes to give beta-allyl-substituted vinylstannanes in moderate to good yields. The allylstannylation proceeds with anti addition exclusively. Allylstannanes bearing an electron-withdrawing group at the beta-position easily reacted with various electron-deficient alkenes to introduce both the allyl and stannyl groups.
  Grant number：08454228
• Creation of Highly Functional Reagents and its Application to Novel Organic Synthesis　　　　　　　　　　　　　　　
  Japan Society for the Promotion of Science, Grants-in-Aid for Scientific Research, Grant-in-Aid for Scientific Research (A), 1995 - 1997
  HOSOMI Akira; TOMINAGA Yoshinori; HAYASHI Nobuyuki; ITO Hajime; MIURA Katsukiyo; HOJO Makoto; DHOGANE Iwao, University of Tsukuba
  Grant amount(Total)：9700000, Direct funding：9700000
  The following results are obtained in this research project.
  1.Manganese Ate Complexes as a New Reducing Agent : Perfectly Regiocontrolled Generation and Reactions of the Mn-Enolates with Electrophiles
  Manganese (II) ate complexes cleanly react with carbonyl compounds bearing a leaving group at the alpha position to generate the enolates of the original ketones, esters, and amides, irrespective of their structure, where the manganate serves as a reductant not an alkylation agent. In this reductive generation of the enolates based on the novel reactivity of the manganese ate complexes, a kind of oxidative addition of a substrate to the ate complex and the reductive elimination of the ligands on manganese are possibly involved as the key processes, while the process equivalent to "metal-halogen exchange" does not seem to be significant. The generality of this reaction was demonstrated in the generation of the enolates of not only aromatic ketones and aliphatic ketones but also an aliphatic ester and amide. As for the synthetic value, this reaction was successfully applied to the perfectly regiospecific generation and reactions of a pair of the regioisomeric enolates corresponding to the unsymmetrical and non-branched aliphatic ketones.
  2.Unprecedented Samarium-Mediated Reactions : Generation of Non-Stabilized Carbonyl Ylids
  Samarium reveals a strong reducing ability and by virtue of this character together with its oxophilicity, is widely applied to organic synthesis in the formation of carbon-carbon bonds and transformation of a variety of functionalities with high selectivities. In the course of our study on the generation and reactions of reactive species, we report herein the generation of novel active species, non-stabilized carbonyl ylids from iodomethyl silyl ethers mediated by samarium, otherwise inaccessible, and their [3+2] cycloadditions to a variety of unsaturated compounds such as aldehydes, alkenes, allenes, and alkynes.
  3.Silicon-Directed Cyclization of Vinylsilanes Bearing Hydroxy Group Catalyzed by an Acid
  The acid-catalyzed cyclization of vinylsilanes bearing a hydroxy group took place cleanly to give tetrahydrofurans and tetrahydropyrans, and the addition of hydroxy group to vinylsilane proceeded in a syn stereoselective fashion.
  Grant number：07555276
• 有機ケイ素化合物を用いる含酸素ヘテロ環合成法の開発　　　　　　　　　　　　　　　
  1996 - 1996
  Grant amount(Total)：1000000, Direct funding：1000000
  Grant number：08750982
• 実践的有機金属反応剤の開発と天然物指向有機合成への新展開　　　　　　　　　　　　　　　
  1996 - 1996
  Grant amount(Total)：2300000, Direct funding：2300000
  Grant number：08245207
• 高配位構造を有する金属活性種と高次触媒系の構築に関する合成化学研究　　　　　　　　　　　　　　　
  1996 - 1996
  Grant amount(Total)：2200000, Direct funding：2200000
  Grant number：08232213
• 希土類錯体を用いる反応活性種の生成と有機合成へ応用　　　　　　　　　　　　　　　
  1996 - 1996
  Grant amount(Total)：1500000, Direct funding：1500000
  Grant number：08220209
• ラジカル的アリルスタニル化反応の開発とその有機合成への応用　　　　　　　　　　　　　　　
  1995 - 1995
  Grant amount(Total)：900000, Direct funding：900000
  Grant number：07750945
• 高配位構造を有する金属活性種と高次触媒系の構築に関する合成化学的研究　　　　　　　　　　　　　　　
  1995 - 1995
  Grant amount(Total)：2200000, Direct funding：2200000
  Grant number：07242211
• 有機銅及び関連化合物の関与する電子移動系の構築　　　　　　　　　　　　　　　
  1995 - 1995
  Grant amount(Total)：2000000, Direct funding：2000000
  Grant number：07215213
• Synthesis of Highly Reactive Organometallic Compounds and its Application to Highly Selective Organic Synthesis　　　　　　　　　　　　　　　
  Japan Society for the Promotion of Science, Grants-in-Aid for Scientific Research, Grant-in-Aid for General Scientific Research (B), 1994 - 1995
  HOSOMI Akira; MIURA Katsukiyo; HOJO Makoto, University of Tsukuba
  Grant amount(Total)：7400000, Direct funding：7400000
  The following results are obtained in this research project.
  1. Creation and Reactions of Carbonyl Ylides and Related 1,3-Dipolar Reagents
  1,3-Dipolar reagents are important and interesting chemical species from both synthetic and theoretical points of view. The novel findings that simple carbonyl ylides, otherwise inaccessible, were indeed expediently generated by the silicon-based 1,3-elimination from alpha-aryl-substituted chloromethyl trimethylsilylmethyl ether under mild and neutral conditions which provided the powerful one-step synthesis of dihydrofurans and tetrahydrofurans and related heterocylesvia [3+2] cycloadditions to a variety of multiple pi-bonds including C=C,C=C,C=O,C=S,C=N,N=N.
  2. Unprecedented Samarium-Mediated Reactions : Generation of Non-Stabilized Carbonyl Ylids
  Samarium reveals a strong reducing ability and by virue of this character together with its oxophilicity, is widely applied to organic synthesis in the formation of carbon-carbon bonds and transformation of a variety of functionalities with high selectivities. In the course of our study on the generation and reactions of reactive species, we report herein the generation of novel active species, nonstabilized carbonyl ylids from iodomethyl silyl ethers mediated by samarium, otherwise inaccessible, and their [3+2] cycloadditions to a variety of unsaturated compounds such as aldehydes, alkenes, allenes, and alkynes.
  3. Direct Generation and Reactions of Sulfur-Substituted Allylcopper Reagents by a Novel Reduction Reaction Using Organocuprate
  Ketene dithioacetals bearing a chlorine atom at an allylic position are cleanly reduced to generate the corresponding allylcopper reagents by treatment with two equimolar amounts of dimethylcuprate derived from cuprous cyanide (Me_2Cu (CN) Li_2). This reaction displays remarkable contrast to hitherto known reactions of cuprates in a sense of highly chemoselective reduction (only metal-halogen exchange reaction occurs) toward substitution reactions and is formally a new type of reaction for the generation of allylcopper species.
  4. Silicon-Directed Cyclization of Vinylsilanes Bearing Hydroxy Group Catalyzed by an Acid
  The acid-catalyzed cyclization of vinylsilanes bearing a hydroxy group took place cleanly to give tetrahydrofurans and tetrahydropyans, and the addition of hydroxy group to vinylsilane proceeded in a syn stereoselective fashion.
  Grant number：06453131
• 希土類錯体を用いる反応活性種の発生と高選択的有機合成への新展開　　　　　　　　　　　　　　　
  1994 - 1994
  Grant amount(Total)：2500000, Direct funding：2500000
  Grant number：06241208
• 有機銅及び関連化合物の関与する電子移動系の構築　　　　　　　　　　　　　　　
  1994 - 1994
  Grant amount(Total)：2200000, Direct funding：2200000
  Grant number：06226213
• Molecular Design for Creation of Synthetic Equivalents and Reseach Development for the Application to Organic Synthesis　　　　　　　　　　　　　　　
  Japan Society for the Promotion of Science, Grants-in-Aid for Scientific Research, Grant-in-Aid for Developmental Scientific Research (B), 1993 - 1994
  HOSOMI Akira; ARATANI Tadatoshi; TOMINAGA Yoshinori; MIURA Katsukiyo; HOJO Makoto, University of Tsukuba
  Grant amount(Total)：5500000, Direct funding：5500000
  1.Synthesis of new di-exo-methylene compounds and fused isoxazoles
  We have prepared and used methyl (trimethylsilylmethyl) acetylenecarboxylate as a dipolarophile and a common key compound leading to precursors for di-exo-methylene compounds which subsequently react with olefins in [4+2] cycloaddition mode to afford fused heterocyclic compounds. We found a new and general route toward the synthesis of the precursor for di-exo-methyleneisoxazolines and their Diels-Alder reactions leading to fused isoxazoles.
  2.New access to di-exo-methylenecyclobutanes via [2+2] cycloaddition of 3-methylthio-4-trimethylsilyl-1,2-butadiene with alkenes mediated by a Lewis acid
  In the course of studies in organic synthesis using allylsilanes and propargylsilanes, we found a new and general route toward the synthesis of di-exo methylenecyclobutanes via the [2+2] cycloaddition of 3-methylthio-4-trimethylsilyl-1,2-butadiene with alkenes promoted by a Lewis acid followed by sequential reactions to sulfones by oxidation and 1,2-elimination. Di-exo-methylenecyclobutanes were also successfully applied to construct a bicyclo [5.2.0] nonane ring system by the [4+3] cycloaddition with an 2-oxyallyl cation. The title compound can be viewed formally as a synthetic equivalent of 1,2,3-butatriene or 1,3-butadien-2,3-diyl.
  3.Creation and Reactions of Carbonyl Ylides and Related 1,3-Dipolar Reagents
  1,3-Dipolar reagents are important and interesting chemical species from both synthetic and theoretical points of view. We found that the novel findings that simple carbonyl ylides, otherwise inaccessible, were indeed expediently generated by the silicon-based 1,3-elimination from alpha-aryl-substituted chloromethyl trimethylsilylmethyl ether under mild and neutral conditions which provided the powerful one-step synthesis of dihydrofurans and tetrahydrofurans and related heterocylesvia[3+2]cycloadditions to a vareity of multiple pi-bonds including C=C,C*C,C=O,C=S,C=N,N=N.
  Grant number：05554022
• 有機ランタノイド及び関連化合物の関与する電子移動系の構築　　　　　　　　　　　　　　　
  1993 - 1993
  Grant amount(Total)：2000000, Direct funding：2000000
  Grant number：05235207
• 有機金属反応剤を利用した有機合成に関する研究　　　　　　　　　　　　　　　
  1993
  Competitive research funding
• Study on Organic Synthesis Using Organosilicon Reagents　　　　　　　　　　　　　　　
  1993
  New organic reactions using organometallics such as organosilicon compounds have been developed for fine oraganic synthesis.
  Competitive research funding