Rapid iododeboronation with and without gold catalysis: application to radiolabelling of arenes

Webster, S., O'Rourke, K. M., Fletcher, C., Pimlott, S. L., Sutherland, A. and Lee, A.-L. (2018) Rapid iododeboronation with and without gold catalysis: application to radiolabelling of arenes. Chemistry: A European Journal, 24(4), pp. 937-943. (doi:10.1002/chem.201704534) (PMID:29105856) (PMCID:PMC5814724)

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Abstract

Radiopharmaceuticals incorporating radioactive iodine in combination with SPECT imaging play a key role in nuclear medicine, with applications in drug development and disease diagnosis. Despite this importance, there are relatively few general methods for incorporating radioiodine into small molecules. Here we describe a rapid, air- and moisture-stable ipso-iododeboronation procedure using NIS, in the non-toxic and green solvent dimethyl carbonate. The fast reaction and mild conditions of the gold-catalysed method led to the development of a highly efficient process for radiolabelling of arenes, which constitutes the first example of an application of homogenous gold catalysis to selective radiosynthesis. This has been exemplified with an effective synthesis of radiolabelled meta-[125I]iodobenzylguanidine, a radiopharmaceutical used for the imaging and therapy of human norepinephrine transporter-expressing tumours.

Item Type:Articles
Status:Published
Refereed:Yes
Glasgow Author(s) Enlighten ID:Pimlott, Dr Sally and Sutherland, Dr Andrew and O'Rourke, Kerry
Authors: Webster, S., O'Rourke, K. M., Fletcher, C., Pimlott, S. L., Sutherland, A., and Lee, A.-L.
College/School:College of Medical Veterinary and Life Sciences > School of Medicine, Dentistry & Nursing
College of Science and Engineering > School of Chemistry
Journal Name:Chemistry: A European Journal
Publisher:Wiley
ISSN:0947-6539
ISSN (Online):1521-3765
Published Online:06 November 2017
Copyright Holders:Copyright © 2018 The Authors
First Published:First published in Chemistry: A European Journal 24(4): 937-943
Publisher Policy:Reproduced under a Creative Commons License

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Project CodeAward NoProject NamePrincipal InvestigatorFunder's NameFunder RefLead Dept
608951Engineering and Physical Sciences Doctoral Training Grant 2012-16Mary Beth KneafseyEngineering and Physical Sciences Research Council (EPSRC)EP/K503058/1VPO VICE PRINCIPAL RESEARCH & ENTERPRISE