Hydroboration of Arynes with N-Heterocyclic Carbene Boranes

被引：40
|
作者：
Taniguchi, Tsuyoshi [1 ]
Curran, Dennis P. [2 ]
机构：
[1] Kanazawa Univ, Sch Pharmaceut Sci, Inst Med Pharmaceut & Hlth Sci, Kanazawa, Ishikawa 9201192, Japan
[2] Univ Pittsburgh, Dept Chem, Pittsburgh, PA 15260 USA
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2014年 / 53卷 / 48期
基金：
美国国家科学基金会;
关键词：
arynes; boranes; hydroboration; main-group chemistry; N-heterocyclic carbenes; CROSS-COUPLING REACTIONS; CARBON-CARBON; ALKENES; BONDS; REDUCTIONS; BORYLATION; ALKYNES;
D O I：
10.1002/anie.201408345
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Arynes were generated in situ from ortho-silyl aryl triflates and fluoride ions in the presence of stable N-heterocyclic carbene boranes (NHC-BH3). Spontaneous hydroboration ensued to provide stable B-aryl-substituted NHC-boranes (NHC-BH2Ar). The reaction shows good scope in terms of both the NHC-borane and aryne components and provides direct access to mono-and disubstituted NHC-boranes. The formation of unusual ortho regioisomers in the hydroboration of arynes with an electron-withdrawing group supports a hydroboration process with hydride-transfer character.
引用
收藏
页码：13150 / 13154
页数：5
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