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
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
收藏
页码:2047 / 2049
页数:3
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