Photoredox/Nickel Dual-Catalyzed Reductive Cross Coupling of Aryl Halides Using an Organic Reducing Agent

A successful protocol for the reductive aryl–aryl cross-coupling of polyfluorinated arenes with a broad range of aryl halides has been developed. Sequential carbon–fluorine bond cleavage and carbon–carbon bond formation are two of the important features of the reaction. Addition of an aryl radical anion to a nickel intermediate was achieved for the first time using polyfluoroarenes as radical precursors. This, in combination with the excellent para selectivity, paves the way for the synthesis of various new multifluorinated biaryl compounds.