title: Lewis acid-promoted hydrofluorination of alkynyl sulfides to generate α-fluorovinyl thioethers.
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.
authors.affiliation: University of St Andrews, School of Chemistry, North Haugh, St Andrews, Fife, KY16 9ST, UK.
authors.forename: Davide
authors.initials: D
authors.lastname: Bello
authors.affiliation: University of St Andrews, School of Chemistry, North Haugh, St Andrews, Fife, KY16 9ST, UK.
authors.forename: David
authors.initials: D
authors.lastname: O'Hagan
keywords: Lewis acids; alkynyl sulfides; hydrofluorination; organofluorine; α-fluorovinyl thioethers