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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.

SUBMITTER: Cosgrove SC

PROVIDER: S-EPMC6115623 | biostudies-literature | 2018 Aug

REPOSITORIES: biostudies-literature

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

Cosgrove Sebastian C SC Plane John M C JMC Marsden Stephen P SP

Chemical science 20180711 32

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 <i>N</i>-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 el ...[more]

PMID: 30310597

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