Heteroatom-Directed Alkylcyanation of Alkynes

被引：111

作者：

Nakao, Yoshiaki ^{[1
]}

Yada, Akira ^{[1
]}

Hiyama, Tamejiro ^{[1
]}

机构：

[1] Kyoto Univ, Dept Chem Mat, Grad Sch Engn, Kyoto 6158510, Japan

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2010年 / 132卷 / 29期

关键词：

CARBON-CARBON BOND; C-C BOND; NICKEL-CATALYZED CARBOCYANATION; ACTIVATION; CLEAVAGE; 2-METHYL-3-BUTENENITRILE; ISOMERIZATION; ACETONITRILE; ALKENES; RHODIUM;

D O I：

10.1021/ja1017078

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Alkanenitriles having a heteroatom such as nitrogen, oxygen, and sulfur at the gamma-position are found to add across alkynes stereo- and regioselectively by nickel/Lewis acid catalysis to give highly substituted acrylonitriles. The heteroatom functionalities likely coordinate to the nickel center to make oxidative addition of the C-CN bonds of the alkyl cyanides kinetically favorable, forming a five-membered nickelacycle intermediate and, thus, preventing beta-hydride elimination to allow the alkylcyanation reaction.

引用

页码：10024 / 10026

页数：3

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