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

Organic & Biomolecular Chemistry Pub Date: 2019-04-18 DOI: 10.1039/C9OB00712A

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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