Regiodivergent and Stereoselective Hydrosilylation of 1,3-Disubstituted Allenes

被引：69

作者：

Miller, Zachary D. ^{[1
]}

Dorel, Ruth ^{[1
]}

Montgomery, John ^{[1
]}

机构：

[1] Univ Michigan, Dept Chem, Ann Arbor, MI 48109 USA

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2015年 / 54卷 / 31期

基金：

美国国家科学基金会;

关键词：

hydrosilylation; regioselectivity; silanes; stereoselectivity; transition-metal catalysis; SILYL-HECK REACTION; HETEROCYCLIC CARBENE LIGANDS; REDUCTIVE COUPLINGS; INTERNAL ALKYNES; REGIOSELECTIVE HYDROSILYLATION; ASYMMETRIC-SYNTHESIS; CHIRAL ALLYLSILANES; ORGANIC-SYNTHESIS; 1ST EXAMPLE; PALLADIUM;

D O I：

10.1002/anie.201503521

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Methods for the highly stereoselective and regiodivergent hydrosilylation of 1,3-disubstituted allenes have been developed. The synthesis of Eallylsilanes is accomplished with palladium NHC catalysts, and trisubstituted Zalkenylsilanes are accessed with nickel NHC catalysts. Unsymmetrically substituted allenes are well tolerated with nickel catalysis and afford Zalkenylsilanes. Evidence for a plausible mechanism was obtained through an isotopic double-labeling crossover study.

引用

页码：9088 / 9091

页数：4

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