Intermolecular Aryl C-H amination using sequential iron and copper catalysis

Mostafa, M. A.B., Calder, E. D.D., Sutherland, A. and Racys, D. T. (2016) Intermolecular Aryl C-H amination using sequential iron and copper catalysis. Chemistry: A European Journal, 23(5), pp. 1044-1047. (doi: 10.1002/chem.201605671) (PMID:27918637)

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Abstract

A mild, efficient and regioselective method for para-amination of activated arenes has been developed through a combination of iron and copper catalysis. A diverse range of products were obtained from an operationally simple one-pot, two-step procedure involving bromination of the aryl substrate with the powerful Lewis acid iron(III) triflimide, followed by a copper(I)-catalysed N-arylation reaction. This two-step dehydrogenative process for the regioselective coupling of aromatic C−H bonds with non-activated amines was applicable to anisole-, phenol-, aniline- and acetanilide-type aryl compounds. Importantly, the arene substrates were used as the limiting reagent and required no protecting-group manipulations during the transformation.

Item Type:Articles
Status:Published
Refereed:Yes
Glasgow Author(s) Enlighten ID:Calder, Mr Ewen and Racys, Dr Daugirdas and Mostafa, Mohamed and Sutherland, Dr Andrew
Authors: Mostafa, M. A.B., Calder, E. D.D., Sutherland, A., and Racys, D. T.
College/School:College of Medical Veterinary and Life Sciences > Institute of Biodiversity Animal Health and Comparative Medicine
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:05 December 2016
Copyright Holders:Copyright © 2017 The Authors
First Published:First published in Chemistry: A European Journal 23(5):1044-1047
Publisher Policy:Reproduced under a Creative Commons License

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Project CodeAward NoProject NamePrincipal InvestigatorFunder's NameFunder RefLead Dept
554791EPSRC Doctoral Training Grant 2010-14Mary Beth KneafseyEngineering & Physical Sciences Research Council (EPSRC)EP/P505534/1VPO VICE PRINCIPAL RESEARCH & ENTERPRISE
618711Impact Acceleration Account (IAA - EPSRC)Jonathan CooperEngineering & Physical Sciences Research Council (EPSRC)EP/K503903/1VPO VICE PRINCIPAL RESEARCH & ENTERPRISE