Asymmetric Copper Hydride-Catalyzed Markovnikov Hydrosilylation of Vinylarenes and Vinyl Heterocycles

被引：140

作者：

Gribble, Michael W., Jr. ^{[1
]}

Pirnot, Michael T. ^{[1
]}

Bandar, Jeffrey S. ^{[1
]}

Liu, Richard Y. ^{[1
]}

Buchwald, Stephen L. ^{[1
]}

机构：

[1] MIT, Dept Chem, Cambridge, MA 02139 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2017年 / 139卷 / 06期

基金：

美国国家卫生研究院;

关键词：

ALKENE HYDROSILYLATION; TERTIARY SILANES; ORGANIC-SYNTHESIS; STYRENES; OLEFINS; LIGAND; IRON; HYDROAMINATION; HYDROSILATION; HYDROBORATION;

D O I：

10.1021/jacs.6b13029

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

We report a highly enantioselective CuH-catalyzed Markovnikov hydrosilylation of vinylarenes and vinyl heterocycles. This method has a broad scope and enables both the synthesis of isolable silanes and the conversion of crude products to chiral alcohols. Density functional theory calculations support a mechanism proceeding by hydrocupration followed by sigma-bond metathesis with a hydrosilane.

引用

页码：2192 / 2195

页数：4

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Auner N., 2005, ORGANOSILICON CHEM M