Heterogeneous Carbon Nitrides Photocatalysis Multicomponent Hydrosulfonylation of Alkynes To Access β-Keto Sulfones with the Insertion of Sulfur Dioxide in Aerobic Aqueous Medium

Abstract

Although hydrosulfonylation of alkynes is an ideal process to generate β-keto sulfones, such an approach is rarely implemented. Here we reported a facile and efficient graphitic carbon nitride (p-g-C3N4) photocatalyzed hydrosulfonylation of alkynes with the insertion of sulfur dioxide in aerobic conditions. Controlled experiments and ESR results indicated both the superoxide radicals and valence band holes played an important role in the reaction. Further isotope experiments confirmed the oxygen atom of the products comes from H2O, while the O2 plays an important role in the reaction by quenching the DABCO radical cation. The metal-free heterogeneous semiconductor is fully recyclable at least 6 times without significant reducing activity. Furthermore, this reaction could be carried out under solar light irradiation and was applicable for a large-scale reaction with conserved results.