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; Miao Yu

doi:10.1021/acs.joc.7b01003

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

J Org Chem. 2017 Jul 7;82(13):7040-7044. doi: 10.1021/acs.joc.7b01003. Epub 2017 Jun 22.

Authors

John R Coombs¹, Kenneth J Fraunhoffer¹, Eric M Simmons¹, Jason M Stevens¹, Steven R Wisniewski¹, Miao Yu¹

Affiliation

¹ Chemical & Synthetic Development, Bristol-Myers Squibb, 1 Squibb Drive, New Brunswick, New Jersey 08903, United States.

PMID: 28594174
DOI: 10.1021/acs.joc.7b01003

Abstract

Conditions have been developed for the palladium-catalyzed cyanation of aryl bromides utilizing the air-stable XantPhos-PdCl₂ precatalyst. By employing a trialkylamine as a reducing agent, the active Pd(0) species is generated in situ, alleviating the need to employ the air-sensitive Pd₂(dba)₃. Twenty-two substituted benzonitriles have been synthesized using this method.

Publication types

Research Support, Non-U.S. Gov't