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

Molloy, J. J., O'Rourke, K., Frias, C. P., Sloan, N., West, M. J., Pimlott, S. L., Sutherland, A. and Watson, A. 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. (doi:10.1021/acs.orglett.9b00942) (PMID:30908055)

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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.

Item Type:Articles
Additional Information:Also funded by CAPES/Science Without Borders (CAPES/SwB Proc. no. BEX5935/13-0).
Status:Published
Refereed:Yes
Glasgow Author(s) Enlighten ID:Pimlott, Dr Sally and Sloan, Miss Nikki and Sutherland, Dr Andrew and Watson, Dr Allan and O'Rourke, Kerry
Authors: Molloy, J. J., O'Rourke, K., Frias, C. P., Sloan, N., West, M. J., Pimlott, S. L., Sutherland, A., and Watson, A. J.B.
College/School:College of Medical Veterinary and Life Sciences > School of Medicine, Dentistry & Nursing
College of Science and Engineering > School of Chemistry
Journal Name:Organic Letters
Publisher:American Chemical Society
ISSN:1523-7060
ISSN (Online):1523-7052
Published Online:25 March 2019
Copyright Holders:Copyright © 2019 American Chemical Society
First Published:First published in Organic Letters 21(7):2488-2492
Publisher Policy:Reproduced under a Creative Commons License

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Project CodeAward NoProject NamePrincipal InvestigatorFunder's NameFunder RefLead Dept
3048960EPSRC-IAA: Early Stage Commercialisation of a PET Imaging Agent for the Detection of Cardiovascular Disease and CancerAndrew SutherlandEngineering and Physical Sciences Research Council (EPSRC)EP/R511705/1Chemistry
608951Engineering and Physical Sciences Doctoral Training Grant 2012-16Mary Beth KneafseyEngineering and Physical Sciences Research Council (EPSRC)EP/K503058/1VPO VICE PRINCIPAL RESEARCH & ENTERPRISE