Regioselective alkenylation of imidazoles by nickel/Lewis acid catalysis

被引：53

作者：

Kanyiva, Kyalo Stephen ^{[1
]}

Lobermann, Florian ^{[1
]}

Nakao, Yoshiaki ^{[1
]}

Hiyama, Tamejiro ^{[1
]}

机构：

[1] Kyoto Univ, Grad Sch Engn, Dept Chem Mat, Kyoto 6158510, Japan

来源：

TETRAHEDRON LETTERS | 2009年 / 50卷 / 26期

关键词：

C-H BONDS; N-HETEROCYCLIC CARBENES; OXIDATIVE ADDITION; COUPLING REACTIONS; ALKYNES; ACTIVATION; SALTS; ANNULATION; PYRROLES; HYDROHETEROARYLATION;

D O I：

10.1016/j.tetlet.2009.02.195

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Nickel/Lewis acid binary catalysis is found effective to direct regioselective alkenylation of imidazoles through C-H bond activation and stereoselective insertion of alkynes. Use of P(t-Bu)(3) as a ligand allows exclusive regioselective C(2)-alkenylation, while PCyp(3) is found effective for C(5)-alkenylation of C(2)-substituted imidazoles. The reaction demonstrates a broad scope of imidazoles and internal alkynes to give trisubstituted ethenes highly regio- and stereoselectively in modest to good yields. (C) 2009 Elsevier Ltd. All rights reserved.

引用

页码：3463 / 3466

页数：4

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