Iron(III)-catalyzed chlorination of activated arenes

Mostafa, M. A.B., Bowley, R. M., Racys, D. T., Henry, M. C. and Sutherland, A. (2017) Iron(III)-catalyzed chlorination of activated arenes. Journal of Organic Chemistry, 82(14), pp. 7529-7537. (doi: 10.1021/acs.joc.7b01225) (PMID:28661157)

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Abstract

A general and regioselective method for the chlorination of activated arenes has been developed. The transformation uses iron(III) triflimide as a powerful Lewis acid for the activation of N-chlorosuccinimide and the subsequent chlorination of a wide range of anisole, aniline, acetanilide and phenol derivatives. The reaction was utilized for the late-stage mono- and di-chlorination of a range of target compounds such as the natural product nitrofungin, the antibacterial agent chloroxylenol and the herbicide chloroxynil. The facile nature of this transformation was demonstrated with the development of one-pot tandem iron-catalyzed dihalogenation processes allowing highly regioselective formation of different carbon-halogen bonds. The synthetic utility of the resulting dihalogenated aryl compounds as building blocks was established with the synthesis of natural products and pharmaceutically relevant targets.

Item Type:Articles
Status:Published
Refereed:Yes
Glasgow Author(s) Enlighten ID:Henry, Mr Martyn and Racys, Dr Daugirdas and Mostafa, Mohamed and Sutherland, Dr Andrew
Authors: Mostafa, M. A.B., Bowley, R. M., Racys, D. T., Henry, M. C., 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
Published Online:29 June 2017
Copyright Holders:Copyright © 2017 American Chemical Society
First Published:First published in Journal of Organic Chemistry 82(14): 7529-7537
Publisher Policy:Reproduced in accordance with the copyright policy of the publisher

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Project CodeAward NoProject NamePrincipal InvestigatorFunder's NameFunder RefLead Dept
618713Impact Acceleration Account (IAA - EPSRC)Jonathan CooperEngineering and Physical Sciences Research Council (EPSRC)EP/K503903/1VPO VICE PRINCIPAL RESEARCH & ENTERPRISE