Beilstein J. Org. Chem.2018,14, 54–83, doi:10.3762/bjoc.14.4
reactive substrates in the method of Oderinde and Johannes [56] (Scheme 22) [57].
Recently, the laboratory of Collins reported the photochemical dual-catalytic cross-coupling of thiols with bromoalkynes, yielding alkynylsulfides (Scheme 23) [58]. Applying 4CzIPN (1,2,3,5-tetrakis(carbazol-9-yl)-4,6
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Graphical Abstract
Scheme 1:
General overview over the sulfur-based substrates and reactive intermediates that are discussed in ...
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-fluorovinyl thioethers is reported which involves the hydrofluorination of alkynylsulfides with 3HF·Et3N, a
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: alkynylsulfides; α-fluorovinyl thioethers; hydrofluorination; Lewis acids; organofluorine; Introduction
, have a spatial and electrostatic profile consistent with the potential to mimic these enzyme intermediates.
There is limited literature for preparing such analogues. We have previously described the preparation of α-fluorovinyl thioethers by hydrofluorination of the corresponding alkynylsulfides using
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Graphical Abstract
Figure 1:
Some spacial and electronic mimetics with fluorine as a design feature [3-6].