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Improving Robustness: In Situ Generation of a Pd(0) Catalyst for the Cyanation of Aryl Bromides

John R. Coombs, Kenneth J. Fraunhoffer, Eric M. Simmons, Jason M. Stevens, Steven R. Wisniewski* and Miao Yu

*Chemical & Synthetic Development, Bristol-Myers Squibb, 1 Squibb Drive, New Brunswick, New Jersey 08903, United States, Email: steven.wisniewskibms.com

J. R. Coombs, K. J. Fraunhoffer, E. M. Simmons, J. M. Stevens, S. R. Wisniewski, Miao Yu, J. Org. Chem., 2017, 82, 7040-7044.

DOI: 10.1021/acs.joc.7b01003 (free Supporting Information)



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Abstract

In the palladium-catalyzed cyanation of aryl bromides utilizing the air-stable XantPhos-PdCl2 precatalyst, DIPEA as a reducing agent generates the active Pd(0) species in situ. Twenty-two substituted benzonitriles have been synthesized.

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Key Words

cyanation


ID: J42-Y2017