Regioselective Synthesis of <i>N</i>-Vinyl Pyrazoles from Vinyl Sulfonium Salts with Diazo Compounds
Shichong Wang, Huayan Xu, Ruoyu Zhang, Siyu Zhang, Yun Chai, Bingchuan Yang, Jingjing Zhao, Yuanqing Xu, Pan Li
Abstract
Herein, we develop a base-promoted regioselective synthesis of N -vinyl pyrazoles from vinyl sulfonium salts with diazo compounds. This metal-free synthetic protocol provides an efficient and practical approach to diverse N -vinyl pyrazoles in good to excellent yields under mild conditions. The reaction appears to experience a [3 + 2] annulation of vinyl sulfonium salts and diazo anions rather than diazo compounds, followed by N -vinylation.
Topics & Concepts
SulfoniumDiazoChemistryRegioselectivityAnnulationOrganic chemistryCombinatorial chemistrySalt (chemistry)CatalysisCyclopropane Reaction MechanismsCatalytic C–H Functionalization MethodsSulfur-Based Synthesis Techniques