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. 2016 Dec 1;7(12):7002-7006.
doi: 10.1039/C6SC02815B. Epub 2016 Jul 28.

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

Derek T Ahneman  1 , Abigail G Doyle  1
Affiliations

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

Derek T Ahneman et al. Chem Sci. .

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.

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Figures

Scheme 1
Scheme 1. Strategies for α-amino C–H arylation where transition metals engage distinct intermediates.
Fig. 1
Fig. 1. Proposed mechanism for α-amino C–H functionalization with aryl halides.
See this image and copyright information in PMC

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