Lewis acid-promoted hydrofluorination of alkynyl sulfides to generate α-fluorovinyl thioethers
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A new method for the preparation of alpha-fluorovinyl thioethers is reported which involves the hydrofluorination of alkynyl sulfides with 3HF center dot Et3N, a process that requires Lewis acid activation using BF3 center dot 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.
Bello , D & O'Hagan , D 2015 , ' Lewis acid-promoted hydrofluorination of alkynyl sulfides to generate α-fluorovinyl thioethers ' Beilstein Journal of Organic Chemistry , vol 11 , pp. 1902-1909 . DOI: 10.3762/bjoc.11.205
Beilstein Journal of Organic Chemistry
© 2015 Bello and O'Hagan; licensee Beilstein-Institut. This is an Open Access article under the terms of the Creative Commons Attribution License (http://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
DescriptionThe authors thank EPSRC for supporting this work and DO’H is grateful for a Royal Society Wolfson Research Merit Award.
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