Cyanoesterification of 1,2-Dienes Catalyzed by Nickel

被引：70

作者：

Hirata, Yasuhiro ^{[1
]}

Inui, Tomohiko ^{[1
]}

Nakao, Yoshiaki ^{[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 | 2009年 / 131卷 / 18期

关键词：

CARBON SINGLE BOND; INTERMOLECULAR ALKYNE INSERTION; BAYLIS-HILLMAN ACETATES; C-CN; SIGMA-BONDS; INTRAMOLECULAR CYANOAMIDATION; CONJUGATE ADDITION; OLEFIN INSERTION; ARYNE INSERTION; ALLYL CYANIDE;

D O I：

10.1021/ja9010282

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Cyanoformate esters add across 1,2-dienes in the presence of a nickel/PMe2Ph catalyst to afford beta-cyano-alpha-methylenealkanoates regioselectively, which are kinetically favored and readily isomerize to thermodynamically favored alpha-cyanomethyl-alpha,beta-unsaturated carboxylates at high temperature under the nickel catalysis, possibly through oxidative addition of the C-CN bond. Similar cyanoesterification products are produced from chloroformate esters, trimethylsilyl cyanide, and 1,2-dienes in the presence of a nickel/dppp catalyst. The resulting cyanoesterification products have a structure of allylic cyanide and thus undergo further allyl cyanation reaction across alkynes with the aid of a nickel/P(4-CF3-C6H4)(3) catalyst to afford highly substituted acrylonitrile derivatives.

引用

页码：6624 / 6631

页数：8

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