Direct Acylation of C(sp(3))-H Bonds Enabled by Nickel and Photoredox Catalysis.

ABSTRACT: Using nickel and photoredox catalysis, the direct functionalization of C(sp(3))-H bonds of N-aryl amines by acyl electrophiles is described. The method affords a diverse range of ?-amino ketones at room temperature and is amenable to late-stage coupling of complex and biologically relevant groups. C(sp(3))-H activation occurs by photoredox-mediated oxidation to generate ?-amino radicals which are intercepted by nickel in catalytic C(sp(3))-C coupling. The merger of these two modes of catalysis leverages nickel's unique properties in alkyl cross-coupling while avoiding limitations commonly associated with transition-metal-mediated C(sp(3))-H activation, including requirements for chelating directing groups and high reaction temperatures.

SUBMITTER: Joe CL 

PROVIDER: S-EPMC4807873 | biostudies-literature | 2016 Mar

REPOSITORIES: biostudies-literature