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-l catalyst. The photoredox and nickel catalytic cycles interact through electron transfer from the single-electron-reduced Cl-TXO ((Cl-TXO)*(-)) to the Ni-l species.

Automated summary

In this study, a photoinduced nickel-catalyzed cross-coupling reaction was achieved with moderate to excellent yields of arylsulfinates and (hetero)aryl halides. The reaction demonstrated a broad substrate scope and good functional group tolerance, leading to the formation of diarylsulfones. The mechanism involved several steps, including oxidative addition, oxidation, reductive elimination, and release of the product. The photoredox and nickel catalytic cycles interacted through electron transfer.