Palladium-catalyzed carbene insertion into vinyl halides and trapping with amines

被引：106

作者：

Devine, Sean K. J. ^{[1
]}

Van Vranken, David L. ^{[1
]}

机构：

[1] Univ Calif Irvine, Dept Chem, Irvine, CA 92697 USA

来源：

ORGANIC LETTERS | 2007年 / 9卷 / 10期

关键词：

D O I：

10.1021/ol070758o

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Palladium is shown to catalyze the three- component coupling of vinyl halides, trimethylsilyldiazomethane, and amines to generate allylamines. The mechanism is believed to involve formation of an R-Pd=CHSiMe3 intermediate that undergoes migration of the vinyl ligand to the empty p-orbital of the carbene ligand. The resulting eta(1)-allylpalladium species forms an eta(3)-allylpalladium intermediate that is trapped by the amine nucleophile. Under the conditions tested, cyclic secondary amines and terminal vinyl iodides give the best results.

引用

页码：2047 / 2049

页数：3

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