Henry, M. C., McGrory, R., Faggyas, R. J., Mostafa, M. A.B. and Sutherland, A. (2019) One-pot ortho-amination of aryl C-H bonds using consecutive iron and copper catalysis: late-stage structural diversification of 3,4-dihydroquinolin-2-one. Organic and Biomolecular Chemistry, 17(18), pp. 4629-4639. (doi: 10.1039/C9OB00712A) (PMID:31020305)
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Abstract
A one-pot approach for ortho-coupling of arenes with non-actived N-nucleophiles has been developed using sequential iron and copper catalysis. Regioselective ortho-activation of anisoles, anilines and phenols was achieved through iron(III) triflimide catalysed iodination, followed by a copper(I)-catalysed, ligand-assisted coupling reaction with N-heterocycle, amide and sulfonamide-based nucleophiles. The synthetic utility of this one-pot, two-step method for the direct amination of ortho-aryl C–H bonds was demonstrated with the late-stage functionalisation of 3,4-dihydroquinolin-2-ones. This allowed the preparation of a TRIM24 bromodomain inhibitor and a series of novel analogues.
Item Type: | Articles |
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Status: | Published |
Refereed: | Yes |
Glasgow Author(s) Enlighten ID: | Henry, Mr Martyn and Mostafa, Mohamed and Sutherland, Professor Andrew and Faggyas, Réka |
Authors: | Henry, M. C., McGrory, R., Faggyas, R. J., Mostafa, M. A.B., and Sutherland, A. |
College/School: | College of Science and Engineering > School of Chemistry |
Journal Name: | Organic and Biomolecular Chemistry |
Publisher: | Royal Society of Chemistry |
ISSN: | 1477-0520 |
ISSN (Online): | 1477-0539 |
Published Online: | 18 April 2019 |
Copyright Holders: | Copyright © 2019 The Authors |
First Published: | First published in Organic and Biomolecular Chemistry 17(18):4629-4639 |
Publisher Policy: | Reproduced under a Creative Commons License |
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