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

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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

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Publication details

The article was received on 17 Apr 2018, accepted on 10 Jul 2018 and first published on 11 Jul 2018


Article type: Edge Article
DOI: 10.1039/C8SC01747F
Citation: Chem. Sci., 2018, Advance Article
  • Open access: Creative Commons BY license
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    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, Advance Article , DOI: 10.1039/C8SC01747F

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