Mechanism of Cu-catalyzed aryl boronic acid halode-boronation using electrophilic halogen: development of a base-catalyzed Iododeboronation for radiolabeling applications

John Molloy, Kerry O’Rourke, Carolina Frias, Nikki Sloan, Matthew West, Sally Pimlott, Andrew Sutherland, Allan J. B. Watson

Research output: Contribution to journalArticlepeer-review

10 Citations (Scopus)

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.
Original languageEnglish
Pages (from-to)2488-2492
Number of pages5
JournalOrganic Letters
Volume21
Issue number7
Early online date25 Mar 2019
DOIs
Publication statusPublished - 5 Apr 2019

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