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

Angewandte Chemie
Candice L Joe, Abigail G Doyle

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 α-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 α-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.

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Aug 2, 2016·The Journal of Organic Chemistry·Megan H ShawDavid W C MacMillan
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