Mild and General Methods for the Palladium-Catalyzed Cyanation of Aryl and Heteroaryl Chlorides

Adam Littke,*† Maxime Soumeillant,*‡ Robert F. Kaltenbach III,§ Robert J. Cherney,§ Christine M. Tarby,§ and Susanne Kiau†;
Process Research and Development, Bristol-Myers Squibb Pharmaceutical Research Institute, 1 Squibb Drive, P.O. Box 191, New Brunswick, New Jersey 08903-0191, Process Research and Development, Bristol-Myers Squibb Pharmaceutical Research Institute, P.O. Box 4000, Princeton, New Jersey 08543-4000, and Discovery Chemistry, Bristol-Myers Squibb Pharmaceutical Research Institute, P.O. Box 4000, Princeton, New Jersey 08543-4000
Org. Lett., 2007, 9 (9), pp 1711–1714
DOI: 10.1021/ol070372d
Publication Date (Web): March 27, 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.

,
†

 Process Research and Development New Brunswick.

,
‡

 Process Research and Development Princeton.

,
§

 Discovery Chemistry Princeton.

, adam.littke@bms.com, ; , maxime.soumeillant@bms.com

Abstract

Abstract Image

New methods for the palladium-catalyzed cyanation of aryl and heteroaryl chlorides have been developed, featuring sterically demanding, electron-rich phosphines. Highly challenging electron-rich aryl chlorides, in addition to electron-neutral and electron-deficient substrates, as well as nitrogen- and sulfur-containing heteroaryl chlorides can all undergo efficient cyanation under relatively mild conditions using readily available materials. In terms of substrate scope and temperature, these methods compare very favorably with the state-of-the-art cyanations of aryl chlorides.

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History

  • Published In Issue April 26, 2007
  • Received February 13, 2007

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