Iridium-Catalyzed Silylation of Aryl C-H Bonds

被引：195

作者：

Cheng, Chen ^{[1
]}

Hartwig, John F. ^{[1
]}

机构：

[1] Univ Calif Berkeley, Dept Chem, Berkeley, CA 94720 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2015年 / 137卷 / 02期

基金：

美国国家科学基金会;

关键词：

DEHYDROGENATIVE SILYLATION; ARENES; BORYLATION; FUNCTIONALIZATION; ACTIVATION; ARYLNITRILES; COMPLEXES; CYANO;

D O I：

10.1021/ja511352u

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A method for the iridium-catalyzed silylation of aryl C-H bonds is described. The reaction of HSiMe(OSiMe3)(2) with arenes and heteroarenes catalyzed by the combination of [Ir(cod)(OMe)](2) and 2,4,7-trimethylphenanthroline occurs with the aromatic compound as the limiting reagent and with high levels of sterically derived regioselectivity. This new catalytic system occurs with a much higher tolerance for functional groups than the previously reported rhodium-catalyzed silylation of aryl C-H bonds and occurs with a wide range of heteroarenes. The silylarene products are suitable for further transformations, such as oxidation, halogenation, and cross-coupling. Late-stage functionalization of complex pharmaceutical compounds was demonstrated.

引用

页码：592 / 595

页数：4

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