Copper-Catalyzed Coupling of Amides and Carbamates with Vinyl Halides

Lei Jiang, Gabriel E. Job, Artis Klapars, and Stephen L. Buchwald*
Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139
Org. Lett., 2003, 5 (20), pp 3667–3669
DOI: 10.1021/ol035355c
Publication Date (Web): September 9, 2003
Copyright © 2003 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.

, sbuchwal@mit.edu

Abstract

Abstract Image

A general and efficient copper-catalyzed method for the amidation of vinyl bromides and iodides has been developed. This protocol uses a combination of 5 mol % copper iodide and 20 mol % N,N-dimethyl ethylenediamine. Substrates bearing ester, silyl ether, and amino groups were successfully coupled under the reaction conditions. The double bond geometry of the vinyl halides was retained under the reaction conditions.

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History

  • Published In Issue October 02, 2003
  • Received July 21, 2003

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