Chemodivergent Synthesis of Sulfonamide and Sulfones from N-Tosylhydrazones by Switching Catalyst and Temperature.

Abstract

A catalyst- and temperature-controlled selective synthesis of sulfonamide and sulfones from N-tosylhydrazones and MBH carbonates has been developed. The use of palladium catalysts exclusively leads to sulfonamide products at room temperature, whereas the selective synthesis of sulfones is dominant for a temperature-controlled coupling reaction without palladium catalysis. Importantly, the catalyst- or temperature-controlled reaction exhibits high nucleophilicity rather than carbene reactivity in these transformations.