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dc.contributor.authorBello, Davide
dc.contributor.authorO'Hagan, David
dc.date.accessioned2015-11-03T10:10:02Z
dc.date.available2015-11-03T10:10:02Z
dc.date.issued2015-10-14
dc.identifier.citationBello , 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.11.205en
dc.identifier.issn1860-5397
dc.identifier.otherPURE: 228184866
dc.identifier.otherPURE UUID: f796ea37-bb37-4529-adf9-3a273949e619
dc.identifier.otherWOS: 000362807300001
dc.identifier.otherScopus: 84962200811
dc.identifier.otherWOS: 000362807300001
dc.identifier.otherORCID: /0000-0002-0510-5552/work/68281293
dc.identifier.urihttp://hdl.handle.net/10023/7731
dc.descriptionThe authors thank EPSRC for supporting this work and DO’H is grateful for a Royal Society Wolfson Research Merit Award.en
dc.description.abstractA 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.extent8
dc.language.isoeng
dc.relation.ispartofBeilstein Journal of Organic Chemistryen
dc.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.en
dc.subjectAlkynyl sulfidesen
dc.subjectAlpha-fluorovinyl thioethersen
dc.subjectHydrofluorinationen
dc.subjectLewis acidsen
dc.subjectOrganofluorineen
dc.subjectEfficient catalysten
dc.subjectVinyl sulfidesen
dc.subjectThiolsen
dc.subjectSubstrateen
dc.subjectMimeticsen
dc.subjectFlourideen
dc.subjectQD Chemistryen
dc.subjectNDASen
dc.subject.lccQDen
dc.titleLewis acid-promoted hydrofluorination of alkynyl sulfides to generate α-fluorovinyl thioethersen
dc.typeJournal articleen
dc.description.versionPublisher PDFen
dc.contributor.institutionUniversity of St Andrews.School of Chemistryen
dc.contributor.institutionUniversity of St Andrews.EaSTCHEMen
dc.contributor.institutionUniversity of St Andrews.Biomedical Sciences Research Complexen
dc.identifier.doihttps://doi.org/10.3762/bjoc.11.205
dc.description.statusPeer revieweden
dc.identifier.urlhttp://www.beilstein-journals.org/bjoc/single/articleFullText.htm?publicId=1860-5397-11-205#supporting-infoen


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