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Chem Sci. 2014 Nov;5(11):4173-4178.

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

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Merck Center for Catalysis at Princeton University, Princeton, New Jersey, 08544, USA.


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 catalyticallygenerated α-amino radical undergoes direct addition to an electrophilic chloroarene.

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