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

2016; Royal Society of Chemistry; Volume: 7; Issue: 12 Linguagem: Inglês

10.1039/c6sc02815b

2041-6539

Derek T. Ahneman, Abigail G. Doyle,

Sulfur-Based Synthesis Techniques

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.