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Palladium-catalyzed carbene insertion into vinyl halides and trapping with amines
被引:106
作者:

Devine, Sean K. J.
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Calif Irvine, Dept Chem, Irvine, CA 92697 USA Univ Calif Irvine, Dept Chem, Irvine, CA 92697 USA

Van Vranken, David L.
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Calif Irvine, Dept Chem, Irvine, CA 92697 USA Univ Calif Irvine, Dept Chem, Irvine, CA 92697 USA
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.
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页码:2047 / 2049
页数:3
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