Chemodivergent Synthesis of Sulfonamide and Sulfones from <i>N</i>-Tosylhydrazones by Switching Catalyst and Temperature
Jingru Jin, Chunyan Li, Rui Wang, Zhimin Xia, Qiongjiao Yan, Wei Wang, Shuang‐Xi Gu, Haifeng Wang, Fen‐Er Chen
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.
Topics & Concepts
SulfonamideChemistryCatalysisPalladiumNucleophileCarbeneReactivity (psychology)Combinatorial chemistryOrganic chemistryPolymer chemistryAlternative medicinePathologyMedicineCyclopropane Reaction MechanismsCatalytic C–H Functionalization MethodsSulfur-Based Synthesis Techniques