Experimental and Theoretical Studies on Cobalt-Catalyzed Regioselective Hydrosilylation of Tetrafluorinated Cyclohexa-1,3-dienes

被引：2

作者：

Nagai, Kento ^{[1
]}

Morishitabara, Suguru ^{[1
]}

Nishi, Yuji ^{[1
]}

Kajimoto, Chihiro ^{[1
]}

Yasui, Motohiro ^{[1
]}

Yumura, Takashi ^{[1
]}

Yamada, Shigeyuki ^{[1
]}

Konno, Tsutomu ^{[1
]}

机构：

[1] Kyoto Inst Technol, Fac Mol Chem & Engn, Kyoto 6068585, Japan

来源：

ORGANIC LETTERS | 2023年 / 25卷 / 38期

关键词：

FLUORINE-CONTAINING ALKYNES; CHALK-HARROD MECHANISM; ASYMMETRIC HYDROSILYLATION; COUPLING REACTION; HOMOGENEOUS CATALYSIS; LIQUID-CRYSTALS; ALKENES; ALLYLSILANES; COMPLEXES; FRAGMENT;

D O I：

10.1021/acs.orglett.3c02453

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Cyclohexa-1,3-dienes bearing a tetrafluoroethylene group underwent highly regioselective hydrosilylation in the presence of 1-10 mol % Co-2(CO)(8) in 1,2-dichloroethane under mild conditions (reflux, 3 h), which led to an abundant yield of homoallylsilanes. Mechanistic studies proved that the reaction proceeds as per the modified Chalk-Harrod mechanism; via DFT calculation, the reason for homoallylsilanes being exclusively obtained was demonstrated. The formal synthesis of a tetrafluorinated negative-type liquid crystal demonstrated the synthetic utility of such hydrosilylation.

引用

页码：6975 / 6981

页数：7

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