Beilstein J. Org. Chem.2015,11, 1902–1909, doi:10.3762/bjoc.11.205
Davide Bello David O'Hagan University of St Andrews, School of Chemistry, North Haugh, St Andrews, Fife, KY16 9ST, UK 10.3762/bjoc.11.205 Abstract A new method for the preparation of α-fluorovinylthioethers 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-fluorovinylthioethers, 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.
Keywords: alkynyl sulfides; α-fluorovinylthioethers; hydrofluorination; Lewis acids; organofluorine; Introduction
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Graphical Abstract
Figure 1:
Some spacial and electronic mimetics with fluorine as a design feature [3-6].