Cobalt-Catalyzed Reductive Coupling of Saturated Alkyl Halides with Activated Alkenes

Paritosh Shukla, Yun-Chu Hsu, and Chien-Hong Cheng*
Department of Chemistry, National Tsing Hua University, Hsinchu 30043, Taiwan
J. Org. Chem., 2006, 71 (2), pp 655–658
DOI: 10.1021/jo052065w
Publication Date (Web): December 15, 2005
Copyright © 2006 American Chemical Society
*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, chcheng@mx.nthu.edu.tw

Abstract

Abstract Image

An efficient cobalt-catalyzed reductive coupling reaction of alkyl halides with electron-withdrawing alkenes (CH2CR1EWG, EWG = electron-withdrawing group) in the presence of water and zinc powder in acetonitrile to give the corresponding Michael-type addition product (RCH2CR1EWG) was described. The methodology is versatile such that unactivated primary, secondary, and tertiary alkyl bromides and iodides and various conjugated alkenes including acrylates, acrylonitrile, methyl vinyl ketone, and vinyl sulfone all successfully participate in this coupling reaction. For the alkyl halides used in the reaction, the iodides generally gave better yields compared to those of the corresponding bromides. It is a unique method employing CoI2dppe, zinc, and alkyl halides, affording conjugate addition products in high yields. Mechanistically, the reaction appears to follow an oxidative addition driven route rather than the previously reported radical route.

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History

  • Published In Issue January 20, 2006
  • Received October 3, 2005

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