Issue 32, 2018

Radical-mediated direct C–H amination of arenes with secondary amines

Abstract

Aryl dialkyl amines, valuable subunits of a wide range of effect chemicals, are accessed by intramolecular amination of aromatic C–H bonds employing UV photolysis of N-chloroamines. The reactions show good functional group tolerance and allow access to a range of fused and bridged polycyclic structures. The homogeneous reaction conditions allow for the one-pot conversion of secondary amines to their arylated derivatives. Experimental and theoretical evidence supports the involvement of electrophilic aminium radicals which react via direct ortho-attack on the arene.

Graphical abstract: Radical-mediated direct C–H amination of arenes with secondary amines

Supplementary files

Article information

Article type
Edge Article
Submitted
17 Apr 2018
Accepted
10 Jul 2018
First published
11 Jul 2018
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2018,9, 6647-6652

Radical-mediated direct C–H amination of arenes with secondary amines

S. C. Cosgrove, J. M. C. Plane and S. P. Marsden, Chem. Sci., 2018, 9, 6647 DOI: 10.1039/C8SC01747F

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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