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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.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.otherPURE: 257381401
dc.identifier.otherPURE UUID: 90a49199-94ed-4224-bca0-7a23d7d68b83
dc.identifier.otherRIS: urn:5FACE1504E72F9B10D452596591ED4CA
dc.identifier.otherScopus: 85061377765
dc.identifier.otherORCID: /0000-0002-9527-6418/work/56861530
dc.identifier.otherWOS: 000461713000033
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.language.isoeng
dc.relation.ispartofChemistry - A European Journalen
dc.rightsCopyright © 2019 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim. This work has been made available online in accordance with the publisher’s policies. This is the author created, accepted version manuscript following peer review and may differ slightly from the final published version. The final published version of this work is available at https://doi.org/10.1002/chem.201806057en
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.description.versionPostprinten
dc.contributor.institutionUniversity of St Andrews. School of Chemistryen
dc.contributor.institutionUniversity of St Andrews. EaSTCHEMen
dc.identifier.doihttps://doi.org/10.1002/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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