Ni-Catalyzed Deoxygenative Cross-Coupling of Alcohols with Aryl Chlorides via an Organic Photoredox Process

Cross-electrophile coupling from naturally abundant materials is of significant value in organic synthesis. Herein, we established a highly efficient deoxygenative cross-coupling reaction using alcohols and industrial preferred aryl chlorides as coupling partners by the merging of photoredox and nickel catalysis with diaryl ketone as a photocatalyst. This methodology features a broad substrate scope and high functional group tolerance, with straightforward application of scale-up synthesis and late-stage modification of structurally complex natural products and pharmaceuticals, including C-4 alkylated pyridines. This protocol most likely proceeds via a HAT and β-scission process to form alkyl radicals from benzoxazolium salt-alcohol adducts.