C–H Fluoroalkylsulfinylation/Intramolecular Rearrangement for Precise Synthesis of Fluoroalkyl Sulfoxides
Shuya Xing, Yu-Yi Zhu, Wen Liu, Yong Liu, Jing Zhang, Huarong Zhang, Yan Wang, Shao‐Fei Ni, Xinxin Shao
Abstract
-functionalized amine scaffolds from arylhydroxylamines is described. The transformation was featured with new electrophilic trifluoromethylthiolated reagents, good functional group tolerance, and late-stage modification of complex bioactive scaffolds, providing a rapid access to prepare numerous trifluoromethyl- and difluoromethyl-substituted sulfoxides. Mechanism studies and density functional theory calculations suggest this reaction goes through a nucleophilic trifluoromethylthiolation of arylhydroxylamine and subsequent internal 2,3-sigmatropic rearrangement involving a sulfur and oxygen transfer process.
Topics & Concepts
ChemistryElectrophileIntramolecular forceNucleophileTrifluoromethylFunctional groupReagentSigmatropic reactionCombinatorial chemistryAmine gas treatingDensity functional theorySulfurMedicinal chemistryStereochemistryOrganic chemistryComputational chemistryCatalysisPolymerAlkylFluorine in Organic ChemistrySulfur-Based Synthesis TechniquesCyclopropane Reaction Mechanisms