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KINOSHITA Hidenori
| Material Science Division | Associate Professor |
| Department of Applied Chemistry |
Researcher information
■ Degree■ Research Keyword
■ Field Of Study
- Nanotechnology/Materials, Synthetic organic chemistry
- Life sciences, Bioorganic chemistry
- Nanotechnology/Materials, Structural/physical organic chemistry
- 2005, Japan
- 2005, Graduate School of Engineering Kyoto University, Graduate School of Engineering, Material Chemistry
- 2002, Japan
- 2002, Graduate School of Engineering Kyoto University, Graduate School of Engineering, Material Chemistry
- 2000, Kyoto University, Faculty of Engineering, School of Industrial Chemistry, Japan
- 2000, Kyoto University, Faculty of Engineering, Industrial Chemistry
Performance information
■ Paper- Palladium-Catalyzed Synthesis of Silylated 3,3′-Bi(3,8-dihydrocyclopenta[a]indenyls) from Silylacetylenes
Taiga Motoyama; Hidenori Kinoshita; Katsukiyo Miura
Organic Letters, Apr. 2025, [Reviewed], [Corresponding]
Scientific journal
DOI：https://doi.org/10.1021/acs.orglett.5c01024
DOI ID：10.1021/acs.orglett.5c01024, ORCID：182540245 - Platinum-Catalyzed Alkenylation of Acetals with Alkenylsilanes
Toma Hattori; Juri Matsuda-Komuro; Yuji Sakurazawa; Naoto Chijiwa; Daiki Fukuda; Hidenori Kinoshita; Katsukiyo Miura
Organic Letters, Apr. 2025, [Reviewed]
Scientific journal
DOI：https://doi.org/10.1021/acs.orglett.5c01096
DOI ID：10.1021/acs.orglett.5c01096, ORCID：181557331 - 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：3, First page：284, Last page：288, Feb. 2025, [Reviewed], [Corresponding]
Scientific journal
DOI：https://doi.org/10.1055/A-2330-0874
DOI ID：10.1055/A-2330-0874, ORCID：166768983, Web of Science ID：WOS:001237508500002 - 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, Jul. 2024, [Reviewed]
Scientific journal
DOI：https://doi.org/10.1021/acs.orglett.4c01735
DOI ID：10.1021/acs.orglett.4c01735, ORCID：162806260 - Synthetic Route to Benzostannoles via Al−Li‐dimetal Intermediate and Their Application to Dibenzofulvene Synthesis
Rei Kurokawa; Hidenori Kinoshita; Katsukiyo Miura
Advanced Synthesis & Catalysis, Volume：366, First page：1523, Last page：1530, Apr. 2024, [Reviewed], [Corresponding]
Scientific journal
DOI：https://doi.org/10.1002/adsc.202301373
DOI ID：10.1002/adsc.202301373, ORCID：153710604 - 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], [Corresponding]
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], [Corresponding]
ABSTRACT: We propose one-pot synthesis of siloles from readily available starting materials. This methodology is practical for the preparation of multisubstituted siloles in good to excellent yields with complete regioselectivity. Sequential reactions, such as lithiation, silylation, and diisobutylaluminum-hydride-promoted cyclization, enable the preparation of the siloles. This transformation provides siloles through two efficient C-Si bond formations in one vessel.
AMER CHEMICAL SOC, English, Scientific journal
DOI：https://doi.org/10.1021/acs.joc.2c00847
DOI ID：10.1021/acs.joc.2c00847, ISSN：0022-3263, eISSN：1520-6904, ORCID：115586401, 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, Last page：132687, Feb. 2022, [Reviewed]
Homolytic hydrobromination of terminal and internal alkynes with a commercially available solution of hydrogen bromide in acetic acid has been investigated for regio- and stereoselective synthesis of bromoalkenes. Under an aerobic atmosphere at room temperature, the reaction of ethynylarenes with a small excess of HBr efficiently gave (2-bromoethenyl)arenes with good to high E-selectivity. (Alk-1-ynyl)arenes, or internal alkynes bearing both phenyl and alkyl groups at the sp-carbons also underwent the air-initiated hydrobromination to exhibit high Z-selectivity under kinetic conditions using a half equivalent of HBr.
Elsevier {BV}, 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, ORCID：109219580, SCOPUS ID：85125436506 - Electrochemical Properties and Electrochromism of 6-Aryl-1,3-bis(trimethylsilyl)fulvenes and Their Derivatives
Tatemura, R.; Yasutake, M.; Kinoshita, H.; Miura, K.
Journal of Organic Chemistry, Volume：87, Number：1, First page：172, Last page：183, 2022, [Reviewed], [Corresponding]
In this study, we have disclosed intriguing electrochromic properties of 6-aryl-1,3-bissilylfulvenes. The electrolyte solutions (0.1 M n-Bu4NClO4 in acetonitrile or dichloromethane) of some 6-aryl-1,3-bissilylfulvenes showed notable color changes when superimposed negative voltages were applied to the solutions. Investigation of the substituents at position 6 revealed that the solution of 1,3-bissilyl-6-anthracenylfulvene exhibited chromic changes under both applied superimposed negative and positive voltages and exhibited a three-color electrochromism. Electrochromic properties of 1,6-diarylfulvenes derived from 6-aryl-1,3-bissilylfulvenes were also investigated. The aryl group at position 1 also contributed to the electrochromism of fulvenes.
American Chemical Society ({ACS}), English, Scientific journal
DOI：https://doi.org/10.1021/acs.joc.1c02133
DOI ID：10.1021/acs.joc.1c02133, ISSN：1520-6904, eISSN：1520-6904, ORCID：109005293, SCOPUS ID：85121901069, Web of Science ID：WOS:000759551400016 - Synthesis of Polysubstituted Germoles and Benzogermoles Using a Substoichiometric Amount of Diisobutylaluminum Hydride
Kojima, K.; Uchida, S.; Kinoshita, H.; Miura, K.
Organic Letters, Volume：23, Number：12, First page：4598, Last page：4602, 2021, [Reviewed], [Corresponding]
We developed a synthetic route to unsymmetrically polysubstituted germoles bearing different substituents from 1-hydrogermyl-4-silyl-1,3-enynes. The reaction proceeded with 0.5 equiv of diisobutylaluminum hydride. Various 2-silylgermoles including benzogermoles were obtained in good to excellent yields. 2-Germylbenzogermoles could be also successfully synthesized from 1-hydrogermyl-4-germyl-1,3-enynes under the same reaction conditions.
American Chemical Society ({ACS}), English, Scientific journal
DOI：https://doi.org/10.1021/acs.orglett.1c01314
DOI ID：10.1021/acs.orglett.1c01314, ISSN：1523-7052, eISSN：1523-7052, ORCID：109005302, SCOPUS ID：85108438077, Web of Science ID：WOS:000664333200019 - Cyclization of 1-ethynyl-2-alkenylbenzenes to naphthalenes using Et2AlCl and DIBAL-H
Yuma Nonoyama; Kazuki Yaguchi; Hidenori Kinoshita; Katsukiyo Miura
Tetrahedron Letters, Volume：62, First page：152682, Last page：152682, Jan. 2021, [Reviewed], [Corresponding]
A one-pot procedure has been developed for the synthesis of substituted naphthalenes from 1-ethynyl-2-alkenylbenzenes. The successive reaction of a variety of 1-ethynyl-2-alkenylbenzenes with BuLi, Et2AlCl, and diisobutylaluminum hydride (DIBAL-H) in one pot gives the corresponding substituted naphthalenes in excellent yields. β, β-Bisaluminated styrenes, which are generated in situ, undergo an intramolecular cyclization reaction to form aluminated naphthalenes. The naphthylaluminum intermediate can be trapped with methanol‑d4 to form the deuterated product, which provides some mechanistic insight. The corresponding iodinated naphthalenes are also obtained on quenching the naphthylaluminum with N-iodosuccinimide (NIS) and iodine.
Elsevier {BV}, 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, ORCID：84686216, SCOPUS ID：85097782886 - 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, [Reviewed], [Corresponding]
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.
American Chemical Society ({ACS}), English, Scientific journal
DOI：https://doi.org/10.1021/acs.orglett.0c00884
DOI ID：10.1021/acs.orglett.0c00884, ISSN：1523-7052, eISSN：1523-7052, ORCID：71448383, SCOPUS ID：85082799009, 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, [Reviewed], [Lead]
In the presence of water and a catalytic amount of InBr3, intramolecular trans-addition of silyl enolates derived from ketones and an aldehyde to alkynes proceeded smoothly to give 4 to 7-membered carbocycles bearing an acyl group. When carboxylic anhydrides were used as electrophiles instead of water, the cyclized products could be functionalized with an additional acyl group.
Elsevier {BV}, Scientific journal
DOI：https://doi.org/10.1016/j.tetlet.2019.05.055
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：1873-3581, eISSN：1873-3581, ORCID：57912117, SCOPUS ID：85066404597 - 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, [Reviewed], [Corresponding]
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.
American Chemical Society ({ACS}), English, Scientific journal
DOI：https://doi.org/10.1021/acs.orglett.9b00144
DOI ID：10.1021/acs.orglett.9b00144, ISSN：1523-7052, eISSN：1523-7052, ORCID：54426895, SCOPUS ID：85062369069, Web of Science ID：WOS:000461843900013 - Development of intramolecular C-C and C-Si bond forming reactions promoted by diisobutylaluminum hydride
Kinoshita, H.; Miura, K.
Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry, Volume：77, Number：1, First page：62, Last page：72, 2019, [Lead, Corresponding]
Diisobutylaluminum hydride (DIBAL-H) is a common reagent in synthetic organic chemistry, and well known as a reducing agent of carbonyl groups and C-C multiple bonds. DIBAL-H is also used for modifications of alkynes. The preparation of haloalkenes via hydroalumination of alkynes and following halodemetallation of the resultant alkenylaluminums is the prime example. However, application of the alkenylaluminums to intramolecular bond formation remained largely unexplored. Recently, our attention has been focused on the reactivity and synthetic use of α - silylalkenylaluminums readly prepared from alkynylsilanes and DIBAL-H. During the course of our research, we succeeded in developing new cyclization reactions by DIBAL-H-promoted C-C and C-Si bond formation, which are valuable for regio-controlled syntheses of substituted benzenes, naphthalenes, indenes, benzosiloles, and siloles. These studies have provided not only efficient synthetic methods for carbocycles and silacycles but also novel information on the reactivity of organoaluminums.
Scientific journal
DOI：https://doi.org/10.5059/yukigoseikyokaishi.77.58
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, ORCID：109005296, 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, Feb. 2018, [Reviewed], [Corresponding]
An efficient method for preparing substituted benzosiloles and unsymmetrically substituted siloles by intramolecular C-Si bond formation has been developed. The reaction of 1-methoxysilyl-2-[2-(trimethylsilyl)ethynyl]benzenes with 1.5 equiv of diisobutylaluminium hydride (DIBAL-H) gave benzosiloles in good to high yields. Similarly 4-methoxysilyl-1-silylalk-3-en-1-ynes were cyclized to multisubstituted siloles. Mechanistic study of this transformation uncovered that the methoxysilyl group was initially converted into the corresponding hydrosilyl group by the action of DIBAL-H, and that the resultant hydrosilanes underwent the DIBAL-H-promoted cyclization to benzosiloles. When 1-hydrosilyl-2-[2-(trimethylsilyl)ethynyl]benzenes were used as substrates, a substoichiometric amount of DIBAL-H was enough for the cyclization. The DIBAL-H-promoted transformation could be applied to regio-defined synthesis of unsymmetrically substituted siloles from 4-hydrosilyl-1-silylalk-3-en-1-ynes. This pre-installation approach provides a straightforward access to multisubstituted siloles with complete regioselection.
Elsevier {BV}, Scientific journal
DOI：https://doi.org/10.1016/j.tet.2018.02.011
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, ORCID：41970399, SCOPUS ID：85041948541 - 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, Mar. 2017, [Reviewed], [Lead]
Scientific journal
DOI：https://doi.org/10.1016/j.tetlet.2017.03.022
DOI ID：10.1016/j.tetlet.2017.03.022, ORCID：31119578 - Diisobutylaluminum Hydride Promoted Cyclization of 1-Hydrosilyl-4-silyl-1,3-enynes to Polysubstituted Siloles
Hidenori Kinoshita; Akihiro Ueda; Hiroki Fukumoto; Katsukiyo Miura
Organic Letters, Volume：19, Number：4, First page：882, Last page：885, Feb. 2017, [Reviewed], [Lead], ［International magazine］
An efficient method for preparing unsymmetrically multisubstituted siloles is described. The reaction of 1-hydrosilyl-4-silyl-1,3-enynes with diisobutylaluminum hydride (DIBAL-H) gave multisubstituted siloles in good to high yields. This method could be applied to the synthesis of benzosiloles using 2-hydrosilyl-1-(silylethynyl)benzenes as substrates. The silole formation was also promoted even by a substoichiometric amount of DIBAL-H. The reaction provides a straightforward method to prepare siloles and benzosiloles.
English, Scientific journal
DOI：https://doi.org/10.1021/acs.orglett.7b00038
DOI ID：10.1021/acs.orglett.7b00038, ORCID：29989206, PubMed ID：28145717 - 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], [Lead]
Elsevier {BV}, Scientific journal
DOI：https://doi.org/10.1016/j.tetlet.2016.10.003
DOI ID：10.1016/j.tetlet.2016.10.003, ORCID：28011420 - 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], [Lead]
Elsevier {BV}, Scientific journal
DOI：https://doi.org/10.1016/j.tetlet.2016.06.123
DOI ID：10.1016/j.tetlet.2016.06.123, ORCID：25025848 - Regioselective Allylation of Carbon Electrophiles with Alkenylsilanes under Dual Catalysis by Cationic Platinum(II) Species
Kinoshita, Hidenori; Kizu, Ryosuke; Horikoshi, Masahiro; Inoue, Gen; Fujimoto, Masayuki; Saito, Masanori; Ichikawa, Junji; Hosomi, Akira; Miura, Katsukiyo
Synthesis-Stuttgart, Volume：48, Number：4, 2016, [Reviewed], [Lead]
Scientific journal
DOI：https://doi.org/10.1055/s-0035-1560380
DOI ID：10.1055/s-0035-1560380, ISSN：1437-210X, ORCID：22757622, SCOPUS ID：84957434861, Web of Science ID：WOS:000369749600005 - Diisobutylaluminum hydride-promoted cyclization of o-(trimethylsilylethynyl)styrenes to substituted naphthalenes
Kinoshita, Hidenori; Yaguchi, Kazuki; Tohjima, Takayuki; Hirai, Nobuyoshi; Miura, Katsukiyo
Tetrahedron Letters, Volume：57, Number：19, 2016, [Reviewed], [Lead]
Scientific journal
DOI：https://doi.org/10.1016/j.tetlet.2016.03.099
DOI ID：10.1016/j.tetlet.2016.03.099, ORCID：24401224, Web of Science ID：WOS:000375338700006 - 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, 2015, [Reviewed], [Lead]
Scientific journal
DOI：https://doi.org/10.1016/j.tetlet.2014.12.077
DOI ID：10.1016/j.tetlet.2014.12.077, ORCID：20026986, Web of Science ID：WOS:000348265000014 - Hydroalumination-Triggered Cyclization of Silylated 1,3-Dien-5-ynes to Polysubstituted Benzenes
Kinoshita, Hidenori; Tohjima, Takayuki; Miura, Katsukiyo
Organic Letters, Volume：16, Number：18, First page：4762, Last page：5, 2014, [Reviewed], [Lead], ［International magazine］
Regiocontrolled synthesis of polysubstituted benzenes from silylated 1,3-dien-5-ynes has been achieved by using diisobutylaluminum hydride (DIBAL-H). Hydroalumination of the alkyne moiety with DIBAL-H triggers the aromatic cyclization, which usually proceeds without rearrangement and loss of the existing substituents. The related unusual cyclizations to different types of polysubstituted benzenes are also described.
English, Scientific journal
DOI：https://doi.org/10.1021/ol5022096
DOI ID：10.1021/ol5022096, ORCID：20026988, PubMed ID：25188533, Web of Science ID：WOS:000342117600018 - Diisobutylaluminum Hydride Promoted Cyclization of o-(Trimethylsilylethynyl)styrenes to Indenes
Kinoshita, Hidenori; Hirai, Nobuyoshi; Miura, Katsukiyo
Journal of Organic Chemistry, Volume：79, Number：17, First page：8171, Last page：81, 2014, [Reviewed], [Lead], ［International magazine］
The reaction of o-(trimethylsilylethynyl)styrenes with diisobutylaluminum hydride (DIBAL-H) provides 2-trimethylsilyl-1H-indenes efficiently. The cyclization mechanism involves regioselective hydroalumination of the alkynyl moiety, geometrical isomerization of the alkenylaluminums formed, and intramolecular carboalumination. With substrates bearing a 2-(trimethylsilyl)ethenyl group (R(1) = Me3Si, R(2) = R(3) = H), bis-silylated benzofulvenes are obtained upon treatment of the reaction mixture with an excess amount of benzaldehyde.
English, Scientific journal
DOI：https://doi.org/10.1021/jo501383v
DOI ID：10.1021/jo501383v, ORCID：20026987, PubMed ID：25093271, Web of Science ID：WOS:000341345400040 - Synthetic utility of tribenzyltin hydride and its derivatives as easily accessible, removable, and decomposable organotin reagents
Yamakawa, Takeshi; Kinoshita, Hidenori; Miura, Katsukiyo
Journal of Organometallic Chemistry, Volume：724, 2013, [Reviewed]
Scientific journal
DOI：https://doi.org/10.1016/j.jorganchem.2012.11.007
DOI ID：10.1016/j.jorganchem.2012.11.007, ORCID：20026992, Web of Science ID：WOS:000314113400017 - Regioselective Synthesis of Multisubstituted Benzenes by Palladium-Catalyzed Intermolecular Reaction of beta-lodo/beta-silylstyrenes with Alkynes
Kinoshita, Hidenori; Takahashi, Hirotoshi; Miura, Katsukiyo
Organic Letters, Volume：15, Number：12, First page：2962, Last page：5, 2013, [Reviewed], [Lead], ［International magazine］
The Pd-catalyzed reaction between β-iodo-β-silylstyrenes and terminal alkynes in i-Pr2NEt gave 1,2,3,5-tetrasubstituted benzenes with complete regioselection. The use of certain silylacetylenes as alkynes enabled efficient synthesis of 1,3,5-trissilyl-2-arylbenzenes, which could be transformed into other multisubstituted benzenes by displacement of the silyl groups.
English, Scientific journal
DOI：https://doi.org/10.1021/ol4010883
DOI ID：10.1021/ol4010883, ORCID：20026991, PubMed ID：23731377, Web of Science ID：WOS:000320979000019 - Platinum-Catalyzed One-Pot Alkenylation of Aldehydes Using Alkynes and Triethylsilane: Dual Catalysis by Platinum(II) Chloride
Kinoshita, Hidenori; Uemura, Ryousuke; Fukuda, Daiki; Miura, Katsukiyo
Organic Letters, Volume：15, Number：21, First page：5538, Last page：5541, 2013, [Reviewed], [Lead]
The PtCl2-catalyzed hydrosilylation of terminal alkynes with triethylsilane and subsequent alkenylation of aldehydes with the resultant (E)-alkenylsilanes in a one-pot manner are described. By adding p-benzoquinone and Lil, the latter alkenylation step proceeds smoothly to give allyl silyl ethers in moderate to high yields. This one-pot alkenylation is tolerant to a reasonable range of functional groups. PtCl2 plays a dual role as hydrosilylation and alkenylation catalysts.
AMER CHEMICAL SOC, English, Scientific journal
DOI：https://doi.org/10.1021/ol4026952
DOI ID：10.1021/ol4026952, ISSN：1523-7060, eISSN：1523-7052, ORCID：20026990, Web of Science ID：WOS:000326615100037 - 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, 2013, [Reviewed]
alpha-Alkylated (dimethylsilyl)acetonitriles ((Me2HSiCRRCN)-R-3-C-4) react spontaneously with aldehydes in DMSO to give beta-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 alpha-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, ORCID：20026989, Web of Science ID：WOS:000322210600067 - Dialkylaluminum Hydride-Promoted Cyclodimerization of Silylated 1,3-Enynes via Skeletal Rearrangement
Kinoshita, Hidenori; Ishikawa, Tomoyuki; Miura, Katsukiyo
Organic Letters, Volume：13, Number：23, First page：6192, Last page：5, 2011, [Reviewed], [Lead], ［International magazine］
The dialkylaluminum hydride-promoted reaction of 1-silylalk-3-en-1-ynes gave symmetrical 1,2,3,5-tetrasubstituted benzenes as single regioisomers. The novel cyclodimerization via skeletal rearrangement can be rationalized by an unprecedented mechanism involving sequential hydroalumination, alkene isomerization, carboalumination, carbon-carbon bond cleavage, and retro-hydroalumination.
English, Scientific journal
DOI：https://doi.org/10.1021/ol202601s
DOI ID：10.1021/ol202601s, ORCID：20026993, PubMed ID：22043921, Web of Science ID：WOS:000297274700015 - Tandem Processes Identified from Reaction Screening: Nucleophilic Addition to Aryl N-Phosphinylimines Employing La(III)-TFAA Activation
Kinoshita, Hidenori; Ingham, Oscar J.; Ong, Winnie W.; Beeler, Aaron B.; Porco, John A., Jr.
Journal of the American Chemical Society, Volume：132, Number：18, First page：6412, Last page：8, 2010, [Reviewed], [Lead], ［International magazine］
Reaction screening of nucleophilic reaction partners for addition to N-diphenylphosphinylimines employing lanthanum(III) triflate as a catalyst and trifluoroacetic anhydride (TFAA) as an activator is reported. A number of tandem processes leading to novel chemotypes including aza-Prins/intramolecular Friedel-Crafts annulations have been identified, and both reaction scope and mechanism further investigated.
English, Scientific journal
DOI：https://doi.org/10.1021/ja100346w
DOI ID：10.1021/ja100346w, ORCID：20026995, PubMed ID：20394364, PubMed Central ID：PMC2881420, Web of Science ID：WOS:000277445400032 - Indium(III)-catalyzed Coupling between Alkynes and Aldehydes to alpha,beta-Unsaturated Ketones
Miura, Katsukiyo; Yamamoto, Kiyomi; Yamanobe, Aya; Ito, Keisuke; Kinoshita, Hidenori; Ichikawa, Junji; Hosomi, Akira
Chemistry Letters, Volume：39, Number：7, 2010, [Reviewed]
Scientific journal
DOI：https://doi.org/10.1246/cl.2010.766
DOI ID：10.1246/cl.2010.766, ORCID：20026994, Web of Science ID：WOS:000280243900044 - Platinum-Catalyzed Nucleophilic Addition of Vinylsilanes at the beta-Position
Miura, Katsukiyo; Inoue, Gen; Sasagawa, Hisashi; Kinoshita, Hidenori; Ichikawa, Junji; Hosomi, Akira
Organic Letters, Volume：11, Number：21, First page：5066, Last page：5069, 2009, [Reviewed]
In the presence of catalytic amounts of PtCl2 and metal Iodides, β-substituted vlnylsllanes reacted with aldehydes at the β-position to give allyl silyl ethers. The Pt-catalyzed addition to aromatic aldehydes proceeded efficiently in the presence of Lil. The combined use of PtCl 2 and Mnl2 was found to be effective In addition to aliphatic aldehydes. © 2009 American Chemical Society.
Scientific journal
DOI：https://doi.org/10.1021/ol902060r
Scopus：https://www.scopus.com/inward/record.uri?partnerID=HzOxMe3b&scp=70350635768&origin=inward
Scopus Citedby：https://www.scopus.com/inward/citedby.uri?partnerID=HzOxMe3b&scp=70350635768&origin=inward
DOI ID：10.1021/ol902060r, ISSN：1523-7060, ORCID：20026997, SCOPUS ID：70350635768, Web of Science ID：WOS:000271097100076 - Platinum(II)-catalyzed Acetal-Ene Reaction: Easy Access to Homoallylic Ethers
Miura, Katsukiyo; Izumi, Hiroyuki; Kinoshita, Hidenori; Ichikawa, Junji; Hosomi, Akira
Chemistry Letters, Volume：38, Number：12, 2009, [Reviewed]
Scientific journal
DOI：https://doi.org/10.1246/cl.2009.1204
DOI ID：10.1246/cl.2009.1204, ORCID：20026996, Web of Science ID：WOS:000273859200039 - Synthesis of medium- and large-sized lactones in an aqueous-organic biphasic system
Kinoshita, H.; Shinokubo, H.; Oshima, K.
Angewandte Chemie-International Edition, Volume：44, Number：16, 2005, [Reviewed], [Lead]
Scientific journal
DOI：https://doi.org/10.1002/anie.200462677
DOI ID：10.1002/anie.200462677, ORCID：20026999, Web of Science ID：WOS:000228709200020 - 1,2-Migration of phosphorus-centered anions on ate-type copper carbenoids and its application for the synthesis of new potent phosphine ligands
Kondo, J; Someya, H; Kinoshita, H; Shinokubo, H; Yorimitsu, H; Oshima, K
Organic Letters, Volume：7, Number：25, First page：5713, Last page：5, 2005, [Reviewed], ［International magazine］
[chemical reaction: see text]. Diorganophosphide anions, which usually function as nontransferable ligands on mixed cuprates, undergo smooth 1,2-migration on ate-type copper carbenoids. Phosphinodisilylmethylcoppers prepared by this protocol are converted into the corresponding phosphines, which can be used as bulky, highly basic and air-stable ligands.
English, Scientific journal
DOI：https://doi.org/10.1021/ol052520a
DOI ID：10.1021/ol052520a, ISSN：1523-7060, ORCID：20026998, PubMed ID：16321029, Web of Science ID：WOS:000233778300043 - Phosphane-free rhodium catalyst in an anionic micellar system for [4+2] annulation of dienynes
Motoda, D.; Kinoshita, H.; Shinokubo, H.; Oshima, K.
Angewandte Chemie - International Edition, Volume：43, Number：14, First page：1860, Last page：2, 2004, [Reviewed], ［International magazine］
English, Scientific journal
DOI：https://doi.org/10.1002/anie.200353123
DOI ID：10.1002/anie.200353123, ISSN：1433-7851, ORCID：109005318, PubMed ID：15054796, SCOPUS ID：3142699863 - Water enables direct use of allyl alcohol for Tsuji-Trost reaction without activators
Kinoshita, H.; Shinokubo, H.; Oshima, K.
Organic Letters, Volume：6, Number：22, 2004, [Reviewed], [Lead]
Scientific journal
DOI：https://doi.org/10.1021/ol048207a
DOI ID：10.1021/ol048207a, ORCID：20027002, Web of Science ID：WOS:000224691900052 - Hydrosilylation of alkynes with a cationic rhodium species formed in an anionic micellar system
Sato, A; Kinoshita, H; Shinokubo, H; Oshima, K
Organic Letters, Volume：6, Number：13, First page：2217, Last page：20, 2004, [Reviewed], ［International magazine］
[reaction: see text] Rhodium-catalyzed hydrosilylation of alkynes in an aqueous micellar system has been developed. A combination of [RhCl(nbd)](2) and bis(diphenylphosphino)propane (dppp) effects (E)-selective hydrosilylation in the presence of sodium dodecyl sulfate (SDS) in water. The (E)-selectivity strongly indicates the formation of a cationic rhodium species via dissociation of the Rh-Cl bond by the action of anionic micelles. The addition of sodium iodide provided (Z)-alkenylsilanes predominantly.
English, Scientific journal
DOI：https://doi.org/10.1021/ol049308b
DOI ID：10.1021/ol049308b, ISSN：1523-7060, ORCID：20027000, PubMed ID：15200324, Web of Science ID：WOS:000222119400035 - Rhodium-catalyzed [2 + 2 + 2] cyclotrimerization in an aqueous-organic biphasic system
Kinoshita, H.; Shinokubo, H.; Oshima, K.
Journal of the American Chemical Society, Volume：125, Number：26, First page：7784, Last page：5, 2003, [Reviewed], [Lead], ［International magazine］
Macrocyclization via rhodium-catalyzed intramolecular [2 + 2 + 2] annulation of triynes has been explored in an aqueous-organic biphasic system. The biphasic system controls the concentration of hydrophobic substrates in the aqueous reaction phase and offers diluted reaction conditions without the use of a slow addition technique. The system also achieves selective cross-annulation between hydrophobic diynes and hydrophilic alkynes.
English, Scientific journal
DOI：https://doi.org/10.1021/ja035438o
DOI ID：10.1021/ja035438o, ISSN：0002-7863, ORCID：109005299, PubMed ID：12822980, SCOPUS ID：0037527845 - Pd(O)-catalyzed reaction of alkynes with trifurylgermane and CO providing acylgermanes: The example of hydrometalcarbonylation of alkynes
Kinoshita, H.; Shinokubo, H.; Oshima, K.
Journal of the American Chemical Society, Volume：124, Number：16, 2002, [Reviewed], [Lead]
Scientific journal
DOI：https://doi.org/10.1021/ja0257016
DOI ID：10.1021/ja0257016, ISSN：0002-7863, ORCID：20027006, SCOPUS ID：0037165724, Web of Science ID：WOS:000175088600026 - Biaryl Synthesis from Two Different Aryl Halides with Tri(2-furyl)germane
Nakamura, T.; Kinoshita, H.; Shinokubo, H.; Oshima, K.
Organic Letters, Volume：4, Number：18, First page：3165, Last page：7, 2002, [Reviewed], ［International magazine］
[reaction: see text] The coupling reaction of germanium compounds with aryl halides has been developed. The Pd(0)-catalyzed reaction of aryl halides with tri(2-furyl)germane provides aryltri(2-furyl)germanes in good yield. The cross-coupling reaction of aryltri(2-furyl)germanes with aryl halides is achieved. This allows facile synthesis of unsymmetrical biaryls from two different aryl halides.
English, Scientific journal
DOI：https://doi.org/10.1021/ol026613t
DOI ID：10.1021/ol026613t, ISSN：1523-7060, ORCID：109005316, PubMed ID：12201743, SCOPUS ID：0012074915 - A room temperature Kharasch reaction catalyzed by Pd(0) in a heterogeneous aqueous system
Motoda, D.; Kinoshita, H.; Shinokubo, H.; Oshima, K.
Advanced Synthesis & Catalysis, Volume：344, Number：3-4, 2002, [Reviewed]
Scientific journal
DOI：https://doi.org/10.1002/1615-4169(200206)344:3/4<261::AID-ADSC261>3.0.CO;2-7
DOI ID：10.1002/1615-4169(200206)344:3/4<261::AID-ADSC261>3.0.CO;2-7, ISSN：1615-4150, ORCID：20027004, SCOPUS ID：0346638609, Web of Science ID：WOS:000176514800004 - Preparation of allylic germanes with tri(2-furyl)germane via π-allylpalladium species
Kinoshita, H.; Shinokubo, H.; Oshima, K.
Synlett, Number：11, 2002, [Reviewed], [Lead]
Scientific journal
DOI：https://doi.org/10.1055/s-2002-34872
DOI ID：10.1055/s-2002-34872, ISSN：0936-5214, ORCID：109005301, SCOPUS ID：0036428018 - Remarkable rate acceleration of Pd(0)-catalyzed hydrogermylation of alkynes and dienes in water
Kinoshita, H.; Nakamura, T.; Kakiya, H.; Shinokubo, H.; Matsubara, S.; Oshima, K.
Organic Letters, Volume：3, Number：16, 2001, [Reviewed], [Lead]
Scientific journal
DOI：https://doi.org/10.1021/ol0161817
DOI ID：10.1021/ol0161817, ISSN：1523-7060, ORCID：20027008, SCOPUS ID：0035833724, Web of Science ID：WOS:000170392300026 - Trialkylmanganate mediated radical addition of triphenylgermane to carbon-carbon multiple bonds
Kinoshita, H.; Kakiya, H.; Oshima, K.
Bulletin of the Chemical Society of Japan, Volume：73, Number：9, 2000, [Reviewed], [Lead]
Scientific journal
DOI：https://doi.org/10.1246/bcsj.73.2159
DOI ID：10.1246/bcsj.73.2159, ORCID：20027009, Web of Science ID：WOS:000089687700028
- Synthesis of functionalized amino-indanes via tandem aza-Prins and intramolecular Friedel-Crafts reactions of aryl N-phosphinylimines
Oscar J. Ingham; Hidenori Kinoshita; Aaron B. Beeler; John A. Porco
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, Volume：240, Aug. 2010
AMER CHEMICAL SOC, English, Summary international conference
ISSN：0065-7727, Web of Science ID：WOS:000208164704648
■ Research projects
- Synthesis of multisubstituted stannoles bearing different substituents and its application to electrochromic materials
Japan Society for the Promotion of Science, Grants-in-Aid for Scientific Research, Grant-in-Aid for Scientific Research (C), 01 Apr. 2023 - 31 Mar. 2026
Saitama University
Grant amount(Total)：4680000, Direct funding：3600000, Indirect funding：1080000
Grant number：23K04748 - 異なる置換基を有する多置換フルベンの合成とエレクトロクロミズム材料への応用
01 Apr. 2020 - 31 Mar. 2023
Grant amount(Total)：4420000, Direct funding：3400000, Indirect funding：1020000
Grant number：20K05505 - Regioselective Synthesis of Polysubstituted Bneznes by Cross Reaction of Silylated 1,3-Enynes Using Diisobutylaluminum Hydride: Synthesis and Application
Japan Society for the Promotion of Science, Grants-in-Aid for Scientific Research Grant-in-Aid for Young Scientists (B), Grant-in-Aid for Young Scientists (B), 01 Apr. 2012 - 31 Mar. 2014
KINOSHITA Hidenori, Saitama University
Grant amount(Total)：4680000, Direct funding：3600000, Indirect funding：1080000
Diisobutylaluminum hydride (DIBAL-H)-promoted reaction of silylated 1,3-enynes provided tetrasubstituted benzenes with complete regioselectivity. The reaction proceeds through dimerization of silylated 1,3-enynes via skeletal rearrengment. Stepwise cross-reaction between two different silylated 1,3-enynes also proceeds to give o,o-bissilylated styrenes in moderate yields. In the latter case, addition of ether enables the stepwise reaction. Silylated acetylenes could also be used instead of the 1,3-enynes. The stilbenes, which could be synthesized by the present reaction, exhibit efficient fluorescence emission in solid and crystal state. The fluorescence quantum yield of one o,o-bissilylstilbenes is 111 times larger than that of dichloromethane solution. Due to the bulky trimethylsilyl group inhibits the crystals from packing tightly to cause concentration quenching. Consequently, the crystals exhibit efficient fluorescence emission.
Grant number：24750082 - Development of Efficient Synthetic Reactions Using Unique Properties of Water
Japan Society for the Promotion of Science, Grants-in-Aid for Scientific Research Grant-in-Aid for Research Activity Start-up, Grant-in-Aid for Research Activity Start-up, 2009 - 2010
KINOSHITA Hidenori, Saitama University
Grant amount(Total)：2704000, Direct funding：2080000, Indirect funding：624000
Water has unique properties which organic solvents do not have. The use of water for organic synthesis is not only environmentally friendly but also increases the efficiency of synthetic reactions. We therefore studied Pt(II)-catalyzed cyclization of alkynyl carbonyls in water. Particularly, our interest was focused on synthetic use of the π-Lewis acidity of Pt(II) catalysts in water. After exploring a wide range of conditions, we came to the realization that the desired cyclization did not proceed. However, during this study, we found that Pt(II)-catalyzed hydrative dimerization of alkynes to α, ss-unsaturated ketones.
Grant number：21850005 - 水中での疎水性反応場における加速効果の有機合成への利用
2002 - 2004
Grant amount(Total)：3000000, Direct funding：3000000
Grant number：02J01960