A phosphane-free catalyst system for the Heck arylation of disubstituted alkenes:: Application to the synthesis of trisubstituted olefins

被引：0

作者：

Gürtler, C ^{[1
]}

Buchwald, SL ^{[1
]}

机构：

[1] MIT, Dept Chem, Cambridge, MA 02139 USA

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 1999年 / 5卷 / 11期

关键词：

alkenes; base effects; Heck reaction; palladium; phase-transfer catalysis;

D O I：

10.1002/(SICI)1521-3765(19991105)5:11<3107::AID-CHEM3107>3.0.CO;2-#

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A new general procedure for the Heck arylation of disubstituted olefins is described. This procedure allows, in many instances, the stereoselective synthesis of trisubstituted olefins. Trisubstituted olefins are easily accessible under mild reaction conditions using a new catalyst system consisting of dicyclohexylamine or methyl-(dicyclohexyl)amine and a phase-transfer catalyst. The choice of base was found to be crucial for the rate and stereoselectivity of the Heck arylation reactions. This method is applicable to the coupling of both electron-deficient and electron-rich aryl halides and displays good stereoselectivity and a high degree: of functional group compatibility. Labeling studies indicate that the source of this selectivity is thermodynamic in nature.

引用

页码：3107 / 3112

页数：6

共 38 条

[1] CONJUGATE ADDITION VS VINYLIC SUBSTITUTION IN PALLADIUM-CATALYZED REACTION OF ARYL HALIDES WITH BETA-SUBSTITUTED-ALPHA,BETA-ENONES AND BETA-SUBSTITUTED-ALPHA,BETA-ENALS [J].