Visible-light mediated cross-coupling of aryl halides with sodium sulfinates via carbonyl-photoredox/nickel dual catalysis

Photoinduced nickel-catalyzed cross-coupling of arylsulfinates (ArSO2-) with (hetero)aryl halides (Ar'-X) via visible light photoexcitation of 2-chloro-thioxanthen-9-one (Cl-TXO) has been achieved in moderate to excellent yields. This photocoupling exhibited a broad substrate scope with good functional group tolerance to give diarylsulfones. The mechanism involves oxidative addition of Ar'-X to Ni(0), oxidation with ArSO2 center dot derived from single-electron-oxidation of ArSO2- by photoexcited Cl-TXO*, reductive elimination and release of the product diaryl sulfone and Ni-I catalyst. The photoredox and nickel catalytic cycles interact through electron transfer from the single-electron-reduced Cl-TXO ([Cl-TXO](center dot-)) to the Ni-I species.

Automated summary

A photoinduced nickel-catalyzed cross-coupling reaction of arylsulfinates with (hetero)aryl halides has been achieved using visible light. The reaction showed a broad substrate scope and good functional group tolerance, providing diarylsulfones in moderate to excellent yields. The mechanism involves oxidative addition, single-electron oxidation, reductive elimination, and electron transfer.