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

页码：3204 / 3207

页数：4

共 32 条

[31] Friedel-Crafts Arylation Reactions of N-Sulfonyl Aldimines or Sulfonamidesulfones with Electron-Rich Arenes Catalyzed by FeCl3•6H2O: Synthesis of Triarylmethanes and Bis-heteroarylarylmethanes
Thirupathi, Ponnaboina
Kim, Sung Soo
JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (15): : 5240 - 5249
[32] Metal-ligand cooperation in C-H and H2 activation by an electron-rich PNPIr(I) system:: Facile ligand dearomatization-aromatization as key steps
Ben-Ari, Eyal
Leitus, Gregory
Shimon, Linda J. W.
Milstein, David
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (48) : 15390 - 15391

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