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镍催化未活化卤代烃的Sonogashira偶联反应:碘代烃、溴代烃和氯代烃的正交官能团化反应

Ni-catalyzed Sonogashira coupling of nonactivated alkyl halides: orthogonal functionalization of alkyl iodides, bromides, and chlorides.

作者信息

Vechorkin Oleg, Barmaz Delphine, Proust Valérie, Hu Xile

机构信息

Laboratory of Inorganic Synthesis and Catalysis, Institute of Chemical Sciences and Engineering, Ecole Polytechnique Fédérale de Lausanne, SB-ISIC-LSCI, BCH 3305, Lausanne CH 1015, Switzerland.

出版信息

J Am Chem Soc. 2009 Sep 2;131(34):12078-9. doi: 10.1021/ja906040t.

Abstract

Ni-catalyzed Sonogashira coupling of nonactivated, beta-H-containing alkyl halides, including chlorides, is reported. The coupling is tolerant to a wide range of functional groups, including ether, ester, amide, nitrile, keto, heterocycle, acetal, and aryl halide, in both coupling partners. The coupling can be selective for a specific C-X bond (X = I, Br, Cl) and allows for orthogonal functionalization of alkyl halides with multiple reactive sites.

摘要

据报道,镍催化未活化的含β-氢烷基卤化物(包括氯化物)的Sonogashira偶联反应。该偶联反应对两种偶联底物中广泛的官能团具有耐受性,包括醚、酯、酰胺、腈、酮、杂环、缩醛和芳基卤化物。该偶联反应可以对特定的C-X键(X = I、Br、Cl)具有选择性,并允许对具有多个反应位点的烷基卤化物进行正交官能化。

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