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Issue 18, 2019
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One-pot ortho-amination of aryl C–H bonds using consecutive iron and copper catalysis

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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.

Graphical abstract: One-pot ortho-amination of aryl C–H bonds using consecutive iron and copper catalysis

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Publication details

The article was received on 28 Mar 2019, accepted on 18 Apr 2019 and first published on 18 Apr 2019


Article type: Paper
DOI: 10.1039/C9OB00712A
Org. Biomol. Chem., 2019,17, 4629-4639
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    One-pot ortho-amination of aryl C–H bonds using consecutive iron and copper catalysis

    M. C. Henry, R. McGrory, R. J. Faggyas, M. A. B. Mostafa and A. Sutherland, Org. Biomol. Chem., 2019, 17, 4629
    DOI: 10.1039/C9OB00712A

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