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Aryl boronic acid-catalysed dehydrative substitution of benzylic alcohols for C-O bond formation

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dc.contributor.authorEstopiñá-Durán, Susana
dc.contributor.authorDonnelly, Liam J.
dc.contributor.authorMclean, Euan B.
dc.contributor.authorHockin, Bryony M.
dc.contributor.authorSlawin, Alexandra M. Z.
dc.contributor.authorTaylor, James
dc.date.accessioned2020-02-11T00:34:45Z
dc.date.available2020-02-11T00:34:45Z
dc.date.issued2019-02-11
dc.identifier257381401
dc.identifier90a49199-94ed-4224-bca0-7a23d7d68b83
dc.identifier85061377765
dc.identifier000461713000033
dc.identifier.citationEstopiñá-Durán , S , Donnelly , L J , Mclean , E B , Hockin , B M , Slawin , A M Z & Taylor , J 2019 , ' Aryl boronic acid-catalysed dehydrative substitution of benzylic alcohols for C-O bond formation ' , Chemistry - A European Journal , vol. Early View . https://doi.org/10.1002/chem.201806057en
dc.identifier.issn0947-6539
dc.identifier.otherRIS: urn:5FACE1504E72F9B10D452596591ED4CA
dc.identifier.otherORCID: /0000-0002-9527-6418/work/56861530
dc.identifier.urihttps://hdl.handle.net/10023/19441
dc.descriptionWe thank the University of St Andrews and the EPSRC for the award of a DTA studentship (S.E.-D.). We would also like to thank the EPSRC, University of St Andrews, and CRITICAT Centre for Doctoral Training for financial support [Ph.D. studentships to B.M.H, E.B.M and L.J.D; Grant code: EP/L016419/1]. J.E.T thanks the Leverhulme Trust for the award of an Early Career Fellowship (Grant code: ECF-2014-005).en
dc.description.abstractA combination of pentafluorophenylboronic acid and oxalic acid catalyses the dehydrative substitution of benzylic alcohols with a second alcohol to form new C-O bonds. This method has been applied to the intermolecular substitution of benzylic alcohols to form symmetrical ethers, intramolecular cyclisations of diols to form aryl-substituted tetrahydrofuran and tetrahydropyran derivatives, and intermolecular crossed-etherification reactions between two different alcohols. Mechanistic control experiments have identified a potential catalytic intermediate formed between the arylboronic acid and oxalic acid.
dc.format.extent2048120
dc.language.isoeng
dc.relation.ispartofChemistry - A European Journalen
dc.subjectAlcoholsen
dc.subjectHomogeneous catalysisen
dc.subjectBoronic acidsen
dc.subjectEtherificationen
dc.subjectSubstitutionen
dc.subjectQD Chemistryen
dc.subjectDASen
dc.subject.lccQDen
dc.titleAryl boronic acid-catalysed dehydrative substitution of benzylic alcohols for C-O bond formationen
dc.typeJournal articleen
dc.contributor.sponsorEPSRCen
dc.contributor.sponsorThe Leverhulme Trusten
dc.contributor.institutionUniversity of St Andrews. School of Chemistryen
dc.contributor.institutionUniversity of St Andrews. EaSTCHEMen
dc.identifier.doi10.1002/chem.201806057
dc.description.statusPeer revieweden
dc.date.embargoedUntil2020-02-11
dc.identifier.grantnumberEP/L016419/1en
dc.identifier.grantnumberECF-2014-005en


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