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Lewis acid-promoted hydrofluorination of alkynyl sulfides to generate α-fluorovinyl thioethers
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dc.contributor.author | Bello, Davide | |
dc.contributor.author | O'Hagan, David | |
dc.date.accessioned | 2015-11-03T10:10:02Z | |
dc.date.available | 2015-11-03T10:10:02Z | |
dc.date.issued | 2015-10-14 | |
dc.identifier | 228184866 | |
dc.identifier | f796ea37-bb37-4529-adf9-3a273949e619 | |
dc.identifier | 000362807300001 | |
dc.identifier | 84962200811 | |
dc.identifier | 000362807300001 | |
dc.identifier.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 | en |
dc.identifier.issn | 1860-5397 | |
dc.identifier.other | ORCID: /0000-0002-0510-5552/work/68281293 | |
dc.identifier.uri | https://hdl.handle.net/10023/7731 | |
dc.description | The authors thank EPSRC for supporting this work and DO’H is grateful for a Royal Society Wolfson Research Merit Award. | en |
dc.description.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. | |
dc.format.extent | 8 | |
dc.format.extent | 314941 | |
dc.language.iso | eng | |
dc.relation.ispartof | Beilstein Journal of Organic Chemistry | en |
dc.subject | Alkynyl sulfides | en |
dc.subject | Alpha-fluorovinyl thioethers | en |
dc.subject | Hydrofluorination | en |
dc.subject | Lewis acids | en |
dc.subject | Organofluorine | en |
dc.subject | Efficient catalyst | en |
dc.subject | Vinyl sulfides | en |
dc.subject | Thiols | en |
dc.subject | Substrate | en |
dc.subject | Mimetics | en |
dc.subject | Flouride | en |
dc.subject | QD Chemistry | en |
dc.subject | NDAS | en |
dc.subject.lcc | QD | en |
dc.title | Lewis acid-promoted hydrofluorination of alkynyl sulfides to generate α-fluorovinyl thioethers | en |
dc.type | Journal article | en |
dc.contributor.institution | University of St Andrews. School of Chemistry | en |
dc.contributor.institution | University of St Andrews. EaSTCHEM | en |
dc.contributor.institution | University of St Andrews. Biomedical Sciences Research Complex | en |
dc.identifier.doi | 10.3762/bjoc.11.205 | |
dc.description.status | Peer reviewed | en |
dc.identifier.url | http://www.beilstein-journals.org/bjoc/single/articleFullText.htm?publicId=1860-5397-11-205#supporting-info | en |
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