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Issue 12, 2016
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C–H functionalization of amines with aryl halides by nickel-photoredox catalysis

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Abstract

We describe the functionalization of α-amino C–H bonds with aryl halides using a combination of nickel and photoredox catalysis. This direct C–H, C–X coupling uses inexpensive and readily available starting materials to generate benzylic amines, an important class of bioactive molecules. Mechanistically, this method features the direct arylation of α-amino radicals mediated by a nickel catalyst. This reactivity is demonstrated for a range of aryl halides and N-aryl amines, with orthogonal scope to existing C–H activation and photoredox methodologies. We also report reactions with several complex aryl halides, demonstrating the potential utility of this approach in late-stage functionalization.

Graphical abstract: C–H functionalization of amines with aryl halides by nickel-photoredox catalysis

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Publication details

The article was received on 25 Jun 2016, accepted on 28 Jul 2016 and first published on 28 Jul 2016


Article type: Edge Article
DOI: 10.1039/C6SC02815B
Citation: Chem. Sci., 2016,7, 7002-7006
  • Open access: Creative Commons BY license
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    C–H functionalization of amines with aryl halides by nickel-photoredox catalysis

    D. T. Ahneman and A. G. Doyle, Chem. Sci., 2016, 7, 7002
    DOI: 10.1039/C6SC02815B

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