Related Experiment Video
Updated: Mar 28, 2026

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
Published on: January 19, 2016
Lewis acid-promoted hydrofluorination of alkynyl sulfides to generate α-fluorovinyl thioethers
1University of St Andrews, School of Chemistry, North Haugh, St Andrews, Fife, KY16 9ST, UK.
Abstract:
A new method for the preparation of α-fluorovinyl thioethers is reported which involves the hydrofluorination of alkynyl sulfides with 3HF·Et3N, a process that requires Lewis acid activation using BF3·Et2O and TiF4. The method gives access to a range of α-fluorovinyl thioethers, some in high stereoselectivity with the Z-isomer predominating over the E-isomer. The α-fluorovinyl thioether motif has prospects as a steric and electronic mimetic of thioester enols and enolates, important intermediates in enzymatic C-C bond forming reactions. The method opens access to appropriate analogues for investigations in this direction.
More Related Videos
10:42Preparation of N-2-alkoxyvinylsulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines
Published on: January 3, 2018
10:10Application of Elemental Lanthanides in the Selective C-F Activation of Trifluoromethylated Benzofulvenes Providing Access to Various Difluoroalkenes
Published on: July 28, 2018
Related Concept Videos
Preparation and Reactions of Sulfides
Preparation and Reactions of Thiols
Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene
Electrophilic Addition to Alkynes: Hydrohalogenation
Conversion of Alcohols to Alkyl Halides
Acid Halides to Esters: Alcoholysis