Copper-Catalyzed Domino Halide Exchange-Cyanation of Aryl Bromides

Jacopo Zanon, Artis Klapars, and Stephen L. Buchwald*
Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139
J. Am. Chem. Soc., 2003, 125 (10), pp 2890–2891
DOI: 10.1021/ja0299708
Publication Date (Web): February 15, 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

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An efficient copper-catalyzed domino halogen exchange-cyanation procedure for aryl bromides was developed utilizing 10 mol % CuI, 20 mol % KI, 1.0 equiv of the inexpensive N,N‘-dimethylethylenediamine as ligand, and 1.2 equiv of NaCN in toluene at 110 °C. The new method represents a significant improvement over the traditional Rosenmund−von Braun reaction:  the reaction conditions are much milder, and the use of stoichiometric amounts of copper(I) cyanide and polar solvents is avoided; therefore the isolation and purification of the aromatic nitrile products is greatly simplified. In addition, the new method exhibits excellent functional group compatibility comparable to that of the analogous Pd-catalyzed cyanation methodology.

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History

  • Published In Issue March 12, 2003
  • Received December 31, 2002

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