Work

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

Year: 2016

Type: article

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.

Source: Angewandte Chemie International Edition

DOI: 10.1002/anie.201511438

Authors: Candice L. Joe, Abigail G. Doyle

Institution: Princeton University

Language: English

Topic: Radical Photochemical Reactions

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funders: Amgen, National Institute of General Medical Sciences

Award: Metal-Catalyzed Cross Coupling with N,O-Acetals and Acetals