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MIURA Katsukiyo
| Material Science Division | Professor |
| Department of Applied Chemistry |
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Researcher information
■ Degree■ Research Keyword
- Organosilicon Chemistry, Substituted Benzenes, Functional Molecule, Regioselective Synthesis
- Organotin Chemistry, Environmentally Friendly Synthesis, Radical Reaction
- Organosilicon Chemistry, Organotin Chemistry, Metal Catalyst, Fine Organic Synthesis
- Organosilicon Chemistry, Environmentally Friendly Synthesis
- Platinum, Indium, Environmentally Friendly Synthesis
- Organosilicon Chemistry, Fine Organic Synthesis, Highly Selective Synthesis, Organometallic Chemistry
- Organic Reaction
- Organic Synthesis
- Nanotechnology/Materials, Synthetic organic chemistry
- Life sciences, Bioorganic chemistry
- Nanotechnology/Materials, Structural/physical organic chemistry
- 01 Oct. 2008
- 01 Oct. 2008, - ,Professor, Saitama University Organic Chemistry
- 01 Oct. 2008, Professor, Saitama University
- 01 Apr. 2007 - 30 Sep. 2008
- 01 Apr. 2007 - 30 Sep. 2008, ,Associate Professor, University of Tsukuba Organic Chemistry
- 01 Apr. 2007 - 30 Sep. 2008, Associate Professor, University of Tsukuba
- 01 Apr. 2004 - 31 Mar. 2007
- 01 Apr. 2004 - 31 Mar. 2007, ,Associate Professor, University of Tsukuba Organic Chemistry
- 01 Apr. 2004 - 31 Mar. 2007, Associate Professor, University of Tsukuba
- 01 Jun. 1997 - 31 Mar. 2004
- 01 Jun. 1997 - 31 Mar. 2004, ,Lecturer, University of Tsukuba Organic Chemistry
- 01 Jun. 1997 - 31 Mar. 2004, Lecturer, University of Tsukuba
- 01 May 1998 - 31 Oct. 1998, California Institute of Technology
- 01 Apr. 1993 - 31 May 1997
- 01 Apr. 1993 - 31 May 1997, ,Research Associate, University of Tsukuba Organic Chemistry
- 01 Apr. 1993 - 31 May 1997, Research Associate, University of Tsukuba
- 01 Apr. 1991 - 31 Mar. 1993
- 01 Apr. 1991 - 31 Mar. 1993, ,Fellowships of the Japan Society for the Promotion of Science for Japanese Junior Scientists
- 01 Apr. 1991 - 31 Mar. 1993, Fellowships of the Japan Society for the Promotion of Science for Japanese Junior Scientists
- Apr. 1990 - Mar. 1993, Kyoto University, Graduate School of Engineering, Department of Industrial Chemistry, Japan
- 1993, Kyoto University, Japan
- 1993, Kyoto University, Graduate School of Engineering, Department of Industrial Chemistry, Japan
- Apr. 1988 - Mar. 1990, Kyoto University, Graduate School of Engineering, Department of Industrial Chemistry, Japan
- 1990, Kyoto University, Japan
- 1990, Kyoto University, Graduate School of Engineering, Department of Industrial Chemistry, Japan
- Apr. 1984 - 1988, Kyoto University, Faculty of Engineering, School of Industrial Chemistry, Japan
- 1988, Kyoto University, Faculty of Engineering, Department of Industrial Chemistry, Japan
Performance information
■ Paper- 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］
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]
English, Scientific journal
DOI：https://doi.org/10.1016/j.tet.2022.132687
Scopus：https://www.scopus.com/inward/record.uri?partnerID=HzOxMe3b&scp=85125436506&origin=inward
Scopus Citedby：https://www.scopus.com/inward/citedby.uri?partnerID=HzOxMe3b&scp=85125436506&origin=inward
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］
English, Scientific journal
DOI：https://doi.org/10.1021/acs.joc.1c02133
Scopus：https://www.scopus.com/inward/record.uri?partnerID=HzOxMe3b&scp=85121901069&origin=inward
Scopus Citedby：https://www.scopus.com/inward/citedby.uri?partnerID=HzOxMe3b&scp=85121901069&origin=inward
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]
Scientific journal
DOI：https://doi.org/10.1021/acs.orglett.1c01314
Scopus：https://www.scopus.com/inward/record.uri?partnerID=HzOxMe3b&scp=85108438077&origin=inward
Scopus Citedby：https://www.scopus.com/inward/citedby.uri?partnerID=HzOxMe3b&scp=85108438077&origin=inward
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 Et
2 AlCl and DIBAL-H
Yuma Nonoyama; Kazuki Yaguchi; Hidenori Kinoshita; Katsukiyo Miura
Tetrahedron Letters, Volume：62, Jan. 2021
Scientific journal
DOI：https://doi.org/10.1016/j.tetlet.2020.152682
Scopus：https://www.scopus.com/inward/record.uri?partnerID=HzOxMe3b&scp=85097782886&origin=inward
Scopus Citedby：https://www.scopus.com/inward/citedby.uri?partnerID=HzOxMe3b&scp=85097782886&origin=inward
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
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
Scientific journal
DOI：https://doi.org/10.1021/acs.orglett.0c00884
Scopus：https://www.scopus.com/inward/record.uri?partnerID=HzOxMe3b&scp=85082799009&origin=inward
Scopus Citedby：https://www.scopus.com/inward/citedby.uri?partnerID=HzOxMe3b&scp=85082799009&origin=inward
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
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
Scientific journal
DOI：https://doi.org/10.1016/j.tetlet.2019.05.055
Scopus：https://www.scopus.com/inward/record.uri?partnerID=HzOxMe3b&scp=85066404597&origin=inward
Scopus Citedby：https://www.scopus.com/inward/citedby.uri?partnerID=HzOxMe3b&scp=85066404597&origin=inward
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
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
Scientific journal
DOI：https://doi.org/10.1021/acs.orglett.9b00144
Scopus：https://www.scopus.com/inward/record.uri?partnerID=HzOxMe3b&scp=85062369069&origin=inward
Scopus Citedby：https://www.scopus.com/inward/citedby.uri?partnerID=HzOxMe3b&scp=85062369069&origin=inward
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
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
Scientific journal
DOI：https://doi.org/10.5059/yukigoseikyokaishi.77.58
Scopus：https://www.scopus.com/inward/record.uri?partnerID=HzOxMe3b&scp=85060898262&origin=inward
Scopus Citedby：https://www.scopus.com/inward/citedby.uri?partnerID=HzOxMe3b&scp=85060898262&origin=inward
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
Scientific journal
DOI：https://doi.org/10.1016/j.tet.2018.02.011
Scopus：https://www.scopus.com/inward/record.uri?partnerID=HzOxMe3b&scp=85041948541&origin=inward
Scopus Citedby：https://www.scopus.com/inward/citedby.uri?partnerID=HzOxMe3b&scp=85041948541&origin=inward
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
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]
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]
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]
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]
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]
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]
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]
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]
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]
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
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
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]
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]
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]
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]
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]
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]
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]
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]
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
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
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
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]
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]
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]
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]
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]
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]
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
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
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]
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
■ Thesis Guidance
■ Affiliated academic society
- 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