Nucleophilic Vinylic Substitution (S<sub>N</sub>V) of Trisubstituted Monofluoroalkenes for the Synthesis of Stereodefined Trisubstituted Alkenes and Divinyl Ethers
Yuwei Zong, Qiao Ma, Gavin Chit Tsui
Abstract
We herein describe a nucleophilic vinylic substitution (SNV) of trisubstituted monofluoroalkenes with excellent stereocontrol (d.r. > 99:1). Starting from (E)-β-monofluoroacrylates, various trisubstituted (E)-alkenes containing O/N/S-substituent groups at the vinylic position can be obtained under simple conditions. Furthermore, (E,E)-divinyl ethers can be generated through dimerization of the monofluoroalkenes, triggered by adventitious water in the reaction mixture.
Topics & Concepts
ChemistrySubstituentNucleophilic substitutionNucleophileSubstitution (logic)Substitution reactionStereochemistryMedicinal chemistryOrganic chemistryCatalysisProgramming languageComputer scienceFluorine in Organic ChemistryCyclopropane Reaction MechanismsCatalytic C–H Functionalization Methods