S<sup>VI</sup>–C Linkage for Allylsulfonximines via BF<sub>3</sub>-Mediated Allylation
Daming Zeng, Suqin Zhao, Wei‐Ping Deng, Xuefeng Jiang
Abstract
A SuFEx linkage reaction between sulfonimidoyl fluoride and allyltrimethylsilane was achieved for the construction of N -modified allylsulfoximines in minutes with BF 3 as a nonmetal difunctional activator enabling the activation of both S–F and C–Si bonds to forge the S–C allyl (sp 3 ) bond swiftly. Mechanistic studies and DFT calculations indicated that the linkage was initiated with the activation of sulfonimidoyl fluoride and then followed with the transfer of the fluoride anion to the TMS group.
Topics & Concepts
ChemistryFluorideLinkage (software)Linkage isomerismActivator (genetics)Medicinal chemistryNonmetalIonStereochemistryInorganic chemistryOrganic chemistryMetalBiochemistryGeneSynthesis and Catalytic ReactionsFluorine in Organic ChemistryChemical Synthesis and Analysis