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

Research output: Contribution to journalArticle

6 Citations (Scopus)
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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.
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

Keywords

  • boronic acid
  • halodeboronation
  • fluorodeboronation

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