Electrophotocatalytic Thiocyanation and Sulfonylation Cyclization of Unactivated Alkenes
Yingchun Ma, Ping Yu, Ruoyu Qin, Run He, Li Zeng, Lou Shi, Shaoguang Sun, Deqiang Liang
Abstract
We report an electrophotocatalytic process that enables the thiocyanation and sulfonylation/cyclization of alkenes. It is applicable to a wide range of unactivated alkenes, using the inexpensive photocatalyst 2,4,6-triphenylpyrylium tetrafluoroborate (TPPT) to produce a diverse array of heterocycles containing sulfonyl and thiocyano groups with good functional group tolerance. The protocol operates under mild, chemical oxidant- and transition-metal-free, with a broad scope of substrates. Preliminary mechanistic studies suggest that the reaction involves a combination of electrolysis and the reductive quenching photocatalytic cycle of TPPT.
Topics & Concepts
ChemistryFunctional groupTetrafluoroborateQuenching (fluorescence)SulfonylElectrolysisCombinatorial chemistryPhotocatalysisOrganic chemistryCatalysisAlkylIonic liquidPhysicsPhysical chemistryElectrolytePolymerElectrodeFluorescenceQuantum mechanicsSulfur-Based Synthesis TechniquesRadical Photochemical ReactionsCatalytic C–H Functionalization Methods