Copper-Catalyzed Double N-Alkenylation of Amides:  An Efficient Synthesis of Di- or Trisubstituted N-Acylpyrroles

Xiyuan Yuan, Xiaobing Xu, Xiaobo Zhou, Jiwei Yuan, Lugen Mai, and Yanzhong Li*
Department of Chemistry and Shanghai Key Laboratory of Green Chemistry and Chemical Processes, East China Normal University, 3663 North Zhongshan Road, Shanghai 200062, P. R. China %yzli@chem.ecnu.edu.cn
J. Org. Chem., 2007, 72 (4), pp 1510–1513
DOI: 10.1021/jo062194s
Publication Date (Web): January 24, 2007
Copyright © 2007 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

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An efficient copper-catalyzed double alkenylation of amides with (1Z,3Z)-1,4-diiodo-1,3-dienes is reported for the first time. The reactions proceed to afford di- or trisubstituted N-acylpyrroles in good to excellent yields using CuI as the catalyst, Cs2CO3 as the base, and rac-trans-N,N‘-dimethylcyclohexane-1,2-diamine as the ligand.

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History

  • Published In Issue February 16, 2007
  • Received October 22, 2006

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