Borenium-Catalyzed Hydroborations of Silyl-Substituted Alkenes and Alkynes with a Readily Available N-Heterocyclic Carbene-Borane

被引：61

作者：

Boussonniere, Anne ^{[1
]}

Pan, Xiangcheng ^{[1
]}

Geib, Steven J. ^{[1
]}

Curran, Dennis P. ^{[1
]}

机构：

[1] Univ Pittsburgh, Dept Chem, Pittsburgh, PA 15260 USA

来源：

ORGANOMETALLICS | 2013年 / 32卷 / 24期

基金：

美国国家科学基金会;

关键词：

CHEMISTRY; BIS(PENTAFLUOROPHENYL)BORANE; ALKENYLSILANES; COMPLEXES; SILANES; ROUTE;

D O I：

10.1021/om400932g

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Borenium-catalyzed hydroboration reactions of a stable, readily available N-heterocyclic carbene-borane with allyl-, alkenyl-, and alkynylsilane substrates provides either standard 1,2-hydroboration products or rearranged 1,1-hydroboration products, depending on the structure of the substrate. A competent catalyst can be generated in situ by addition of bis(trifluoromethane)sulfonimide or diiodine. In a typical 1,2-hydroboration, reaction of 1,3-dimethylimidazol-2-ylidine borane (diMe-Imd-BH3) with 1,2-bis(trimethylsilyl)ethene provides 1,3-dimethylimidazol-2-ylidine (1,2-bis(trimethylsilyl)ethyl)borane (diMe-Imd-BH2CH-(TMS)CH2TMS)) as a stable product. In a typical 1,1-hydroboration, the reaction of diMe-Imd-BH3 with bis(trimethylsilyl)-ethyne provides 1,3-dimethylimidazol-2-ylidine-bis(2,2-bis(trimethylsilyl)ethenyl)borane (diMe-Imd-BH(CH=C(TMS)(2))(2) again as a stable product.

引用

页码：7445 / 7450

页数：6

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