Zn/CuI-Mediated Coupling of Alkyl Halides with Vinyl Sulfones, Vinyl Sulfonates, and Vinyl Sulfonamides

Matthew M. Zhao,* Chuanxing Qu, and Joseph E. Lynch
Process Research, Merck Research Laboratories, Merck & Co., Inc., P.O. Box 2000, Rahway, New Jersey 07065 matthew_zhao@merck.com
J. Org. Chem., 2005, 70 (17), pp 6944–6947
DOI: 10.1021/jo050500g
Publication Date (Web): July 20, 2005
Copyright © 2005 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.

Abstract

Abstract Image

A novel high-yielding Zn/CuI-mediated coupling method of alkyl halides with vinyl sulfones, vinyl sulfonates, and vinyl sulfonamides is described. This protocol is applicable for primary, secondary, and tertiary alkyl iodides and bromides. Alkyl chlorides and aryl and vinyl halides were unreactive under the reaction conditions. Formamide was found to be a superior solvent for obtaining high yields.

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History

  • Published In Issue August 19, 2005
  • Received March 11, 2005

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