Friedel-Crafts-Type Intermolecular C-H Silylation of Electron-Rich Arenes Initiated by Base-Metal Salts

被引：82
|
作者：
Yin, Qin [1 ]
Klare, Hendrik F. T. [1 ]
Oestreich, Martin [1 ]
机构：
[1] Tech Univ Berlin, Inst Chem, Str 17 Juni 115, D-10623 Berlin, Germany
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2016年 / 55卷 / 09期
关键词：
C-H activation; electrophilic substitution; hydrosilanes; Lewis acids; Si-H activation; BOND-CLEAVAGE; CATALYZED SILYLATION; N-SILYLATION; HYDROSILANES; ACTIVATION; BENZENE; INDOLES; FUNCTIONALIZATION; MECHANISM; COMPLEX;
D O I：
10.1002/anie.201510469
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
An electrophilic aromatic substitution (SEAr) with a catalytically generated silicon electrophile is reported. Essentially any commercially available base-metal salt acts as an initiator/catalyst when activated with NaBAr4F. The thus-generated Lewis acid then promotes the SEAr of electron-rich arenes with hydrosilanes but not halosilanes. This new C-H silylation was optimized for FeCl2/NaBAr4F, affording good yields at catalyst loadings as low as 0.5mol%. The procedure is exceedingly straightforward and comes close to typical Friedel-Crafts methods, where no added base is needed to absorb the released protons.
引用
收藏
页码：3204 / 3207
页数：4
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