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C-H functionalization of amines with aryl halides by nickel-photoredox catalysis.

ABSTRACT: We describe the functionalization of ?-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 ?-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.

SUBMITTER: Ahneman DT

PROVIDER: S-EPMC5207500 | biostudies-literature | 2016 Dec

REPOSITORIES: biostudies-literature

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C-H functionalization of amines with aryl halides by nickel-photoredox catalysis.

Ahneman Derek T DT Doyle Abigail G AG

Chemical science 20160728 12

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 <i>N</i>-aryl amines, with orthogonal ...[more]

PMID: 28058105

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