Mechanism of Cu-catalyzed aryl boronic acid halodeboronation using electrophilic halogen : development of a base-catalyzed iododeboronation for radiolabeling applications

Molloy, John J. and O'rourke, Kerry M. and Frias, Carolina P. and Sloan, Nikki L. and West, Matthew J. and Pimlott, Sally L. and Sutherland, Andrew and Watson, Allan J.B. (2019) Mechanism of Cu-catalyzed aryl boronic acid halodeboronation using electrophilic halogen : development of a base-catalyzed iododeboronation for radiolabeling applications. Organic Letters, 21 (7). pp. 2488-2492. ISSN 1523-7060

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    Abstract

    An investigation into the mechanism of Cu-catalyzed aryl boronic acid halodeboronation using electrophilic halogen reagents is reported. Evidence is provided to show that this takes place via a boronate-driven ipso-substitution pathway and that 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 that is amenable to the preparation of 125I-labeled products for SPECT applications.