Radical Reactions of N-Heterocyclic Carbene Boranes with Organic Nitriles: Cyanation of NHC-Boranes and Reductive Decyanation of Malononitriles

被引：107

作者：

Kawamoto, Takuji ^{[1
]}

Geib, Steven J. ^{[1
]}

Curran, Dennis P. ^{[1
]}

机构：

[1] Univ Pittsburgh, Dept Chem, Pittsburgh, PA 15260 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2015年 / 137卷 / 26期

基金：

美国国家科学基金会;

关键词：

SUBSTITUTION-REACTIONS; INITIATORS; COMPLEXES; HALIDES; GENERATION; RESONANCE; CYANO;

D O I：

10.1021/jacs.5b04677

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The observation that NHC-boryl radicals abstract cyano groups from various organic nitriles has been parlayed into two complementary transformations. In the main group chemistry aspect, reactions of various NHC-boranes with simple organic dinitriles selectively provide stable NHC-boryl mono- or dinitriles, depending on the nitrile source. In the organic synthesis aspect, reaction of malononitriles and related derivatives with readily available 1,3-dimethylimidazol-2-ylidene borane provides reductively decyanated products in good yields.

引用

页码：8617 / 8622

页数：6

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