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Lewis acid-promoted hydrofluorination of alkynyl sulfides to generate α-fluorovinyl thioethers

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OHagan_2015_BJOC_Lewis_CC.pdf (307.5Kb)
Date
14/10/2015
Author
Bello, Davide
O'Hagan, David
Keywords
Alkynyl sulfides
Alpha-fluorovinyl thioethers
Hydrofluorination
Lewis acids
Organofluorine
Efficient catalyst
Vinyl sulfides
Thiols
Substrate
Mimetics
Flouride
QD Chemistry
NDAS
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Abstract
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.
Citation
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 . https://doi.org/10.3762/bjoc.11.205
Publication
Beilstein Journal of Organic Chemistry
Status
Peer reviewed
DOI
https://doi.org/10.3762/bjoc.11.205
ISSN
1860-5397
Type
Journal article
Rights
© 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.
Description
The authors thank EPSRC for supporting this work and DO’H is grateful for a Royal Society Wolfson Research Merit Award.
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  • University of St Andrews Research
URL
http://www.beilstein-journals.org/bjoc/single/articleFullText.htm?publicId=1860-5397-11-205#supporting-info
URI
http://hdl.handle.net/10023/7731

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