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Issue 11, 2014
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Amine α-heteroarylation via photoredox catalysis: a homolytic aromatic substitution pathway

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Abstract

The direct α-heteroarylation of tertiary amines has been accomplished via photoredox catalysis to generate valuable benzylic amine pharmacophores. A variety of five- and six-membered chloroheteroarenes are shown to function as viable coupling partners for the α-arylation of a diverse range of cyclic and acyclic amines. Evidence is provided for a homolytic aromatic substitution mechanism, in which a catalytically-generated α-amino radical undergoes direct addition to an electrophilic chloroarene.

Graphical abstract: Amine α-heteroarylation via photoredox catalysis: a homolytic aromatic substitution pathway

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Supplementary files

Article information


Submitted
19 Jul 2014
Accepted
04 Aug 2014
First published
04 Aug 2014

Chem. Sci., 2014,5, 4173-4178
Article type
Edge Article
Author version available

Amine α-heteroarylation via photoredox catalysis: a homolytic aromatic substitution pathway

C. K. Prier and D. W. C. MacMillan, Chem. Sci., 2014, 5, 4173
DOI: 10.1039/C4SC02155J

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