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Paper | Special issue | Vol 90, No. 1, 2015, pp.271-297
Published online, 28th May, 2014
DOI: 10.3987/COM-14-S(K)18
■ Copper Mediated Formation of Carbon-Heteroatom Bonds Using Organoboron Reagents and Ultrasound

Bryan J. Musolino and George W. Kabalka*

*Chemistry Department, University of Tennessee, Knoxville, Tennessee, 37996-1600, U.S.A.

Abstract

This report summarizes research efforts focused on copper acetate mediated reactions to form new carbon-heteroatom bonds using organoboron reagents under ultrasound irradiation. The method involves the application of ultrasound irradiation to the Chan-Evans-Lam reaction to achieve O-arylation of phenols, N-arylation of anilines and indoles, and S-arylation of thiols. Ultrasound irradiation was found to decrease reaction times from 72 hours to 4 hours while improving the product yields an average of 20%.1 Representative C-O, C-N, and C-S coupling reactions were successfully scaled-up from the milligram to gram levels while maintaining good product yields offering potential applications in industrial processes.