Silver(I)-catalyzed iodination of Arenes: Tuning the Lewis acidity of N-iodosuccinimide activation

Racys, D. T., Sharif, S. A.I., Pimlott, S. L. and Sutherland, A. (2016) Silver(I)-catalyzed iodination of Arenes: Tuning the Lewis acidity of N-iodosuccinimide activation. Journal of Organic Chemistry, 81(3), pp. 772-780. (doi: 10.1021/acs.joc.5b02761) (PMID:26795534)

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Abstract

A mild and rapid method for the iodination of arenes that utilizes silver(I) triflimide as a catalyst for activation of N-iodosuccinimide has been developed. The transformation was found to be general for a wide range of anisole, aniline, acetanilide, and phenol derivatives and allowed the late-stage iodination of biologically active compounds such as PIMBA, a SPECT imaging agent of breast cancer, and (−)-IBZM, a dopamine D2 receptor antagonist. The method was also modified for the radioiodination of arenes using a one-pot procedure involving the in situ generation of [125I]-N-iodosuccinimide followed by the silver(I)-catalyzed iodination.

Item Type:Articles
Status:Published
Refereed:Yes
Glasgow Author(s) Enlighten ID:Pimlott, Dr Sally and Racys, Dr Daugirdas and Sutherland, Professor Andrew
Authors: Racys, D. T., Sharif, S. A.I., Pimlott, S. L., and Sutherland, A.
College/School:College of Science and Engineering > School of Chemistry
Journal Name:Journal of Organic Chemistry
Publisher:American Chemical Society
ISSN:0022-3263
ISSN (Online):1520-6904
Copyright Holders:Copyright © 2016 The Authors
First Published:First published in Journal of Organic Chemistry 81(3):772-780
Publisher Policy:Reproduced under a Creative Commons License

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Project CodeAward NoProject NamePrincipal InvestigatorFunder's NameFunder RefLead Dept
618711Impact Acceleration Account (IAA - EPSRC)Jonathan CooperEngineering & Physical Sciences Research Council (EPSRC)EP/K503903/1VICE PRINCIPAL RESEARCH & ENTERPRISE