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

Derek T. Ahneman, Abigail G. Doyle

Research output: Contribution to journalArticlepeer-review

73 Scopus citations

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.

Original languageEnglish (US)
Pages (from-to)7002-7006
Number of pages5
JournalChemical Science
Volume7
Issue number12
DOIs
StatePublished - 2016

All Science Journal Classification (ASJC) codes

  • Chemistry(all)

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