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Synfacts 2007(8): 0798-0798  
DOI: 10.1055/s-2007-968798
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart · New York

Palladium-Catalyzed Cyanation of Aryl and Heteroaryl Chlorides

Contributor(s): Victor Snieckus, Jignesh J. Patel
A. Littke*, M. Soumeillant, R. F. Kaltenbach, III, R. J. Cherney, C. M. Tarby, S. Kiau
Bristol-Myers Squibb Pharmaceutical Research Institutes, New Brunswick and Princeton, USA
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Publication History

Publication Date:
24 July 2007 (online)

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Significance

Demonstrated here is a general and very mild method for Pd-catalyzed cyanation of aryl and heteroaryl chlorides using sterically demanding and electron-rich phosphine ligands. Many Pd sources and ligands were screened using Zn flakes as cocatalyst and Zn(CN)2 as the cyanating agent; catalysts A and B were found to be the optimized systems. Electronically rich, neutral and deficient aryl chlorides were efficiently cyanated. Significantly, chloro indoles as well as several types of π-deficient chloro heterocycles were effectively converted into their corresponding nitriles.