Mechanism of Cu-Catalyzed Aryl Boronic Acid Halodeboronation Using Electrophilic Halogen: Development of a Base-Catalyzed Iododeboronation for Radiolabeling Applications

John J. Molloy, Kerry M. O'Rourke, Carolina P. Frias, Nikki L. Sloan, Matthew J. West, Sally L. Pimlott, Andrew Sutherland*, Allan J. B. Watson*

*University of Glasgow, Joseph Black Building, University Avenue, Glasgow, G12 8QQ; University of St Andrews, North Haugh, St Andrews, Fife, KY16 9ST, U.K., Email: andrew.sutherlandglasgow.ac.uk, aw260st-andrews.ac.uk

J. J. Molloy, K. M. O'Rourke, C. P. Frias, N. L. Sloan, M. J. West, S. L. Pimlott, A. Sutherland, A. J. B. Watson, Org. Lett., 2019, 21, 2488-2492.

DOI: 10.1021/acs.orglett.9b00942

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Abstract

Cu-catalyzed aryl boronic acid halodeboronation takes place via a boronate-driven ipso-substitution pathway. Cu is not required for these processes to operate: general Lewis base catalysis is operational. This in turn allows the rational development of a general, simple, and effective base-catalyzed halodeboronation.

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Key Words

aryl iodides, NIS

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ID: J54-Y2019