Palladium-Catalyzed Fluoroalkylation via C(sp<sup>3</sup>)–S Bond Cleavage of Vinylsulfonium Salts
Yuan He, Zilong Huang, Juan Ma, Fei Huang, Jie Lin, Hongmei Wang, Bao‐Hua Xu, Yong‐Gui Zhou, Zhengkun Yu
Abstract
An interrupted Pummerer/palladium-catalyzed fluoro-alkylation strategy was developed for alkenyl C–H fluoroalkylthiolation. Palladium-catalyzed ring-opening fluoroalkylation via aliphatic C–S bond cleavage of the vinylsulfonium salts efficiently afforded fluoroalkylthiolated alkene derivatives from readily available alkene substrates and CsF. The protocol features broad substrate scopes and good functional group tolerance under an air atmosphere. The practicability of the synthetic method was demonstrated by transforming the multisubstituted alkene products to diverse fluoroalkylthiolated N-heterocycles.
Topics & Concepts
AlkeneChemistryPalladiumCatalysisCleavage (geology)Bond cleavageAlkylationFunctional groupRing (chemistry)Medicinal chemistryCombinatorial chemistryOrganic chemistryPolymerFracture (geology)Geotechnical engineeringEngineeringFluorine in Organic ChemistrySulfur-Based Synthesis TechniquesCatalytic C–H Functionalization Methods