Copper−Carbene Complexes as Catalysts in the Synthesis of Functionalized Styrenes and Aliphatic Alkenes

Hélène Lebel,*† Michaël Davi,† Silvia Díez-González,‡§ and Steven P. Nolan‡§
Dpartement de Chimie, Universit de Montral, P.O. Box 6128, Station Downtown, Montral, Qubec, Canada, H3C 3J7, Department of Chemistry, University of New Orleans, New Orleans, Louisiana 70148, and Institute of Chemical Research of Catalonia (ICIQ), Av. Pasos Catalans 16, 43007 Tarragona, Spain
J. Org. Chem., 2007, 72 (1), pp 144–149
DOI: 10.1021/jo061781a
Publication Date (Web): December 6, 2006
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.

,
†

 Université de Montréal.

,
‡

 University of New Orleans.

,
§

 Institute of Chemical Research of Catalonia (ICIQ).

, helene.lebel@umontreal.ca

Abstract

Abstract Image

(NHC)−Cu (NHC = N-heterocyclic carbene) complexes efficiently catalyzed the methylenation of a variety of aliphatic and aromatic aldehydes and ketones in the presence of trimethylsilyldiazomethane, triphenylphosphine, and 2-propanol. The copper catalysts are not only inexpensive compared to rhodium complexes, but they also exhibit better functional group compatibility with aromatic aldehydes and ketones. Indeed very high yields were obtained for the formation of styrenes containing nitro, trifluoromethyl, amino, and ester groups, as well as for pyridine-, pyrrole-, and indole-substituted alkenes.

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History

  • Published In Issue January 05, 2007
  • Received August 29, 2006

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