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

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)

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
• 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

Project Code	Award No	Project Name	Principal Investigator	Funder's Name	Funder Ref	Lead Dept
70110	1	EPSRC 2015 DTP	Mary Beth Kneafsey	Engineering and Physical Sciences Research Council (EPSRC)	EP/M508056/1	R&I - RESEARCH STRATEGY & INNOVATION