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dc.contributor.authorLancefield, Christopher S.
dc.contributor.authorFölker, Bart
dc.contributor.authorCioc, Razvan C.
dc.contributor.authorStanciakova, Katarina
dc.contributor.authorBulo, Rosa E.
dc.contributor.authorLutz, Martin
dc.contributor.authorCrockatt, Marc
dc.contributor.authorBruijnincx, Pieter C.A.
dc.date.accessioned2020-11-02T10:30:07Z
dc.date.available2020-11-02T10:30:07Z
dc.date.issued2020-10-15
dc.identifier.citationLancefield , C S , Fölker , B , Cioc , R C , Stanciakova , K , Bulo , R E , Lutz , M , Crockatt , M & Bruijnincx , P C A 2020 , ' Dynamic trapping as a selective route to renewable phthalide from biomass-derived furfuryl alcohol ' , Angewandte Chemie - International Edition , vol. Early View . https://doi.org/10.1002/anie.202009001en
dc.identifier.issn1433-7851
dc.identifier.otherPURE: 270929770
dc.identifier.otherPURE UUID: 0537fb7c-e5d2-4fbf-9a21-6df3f4a44c8f
dc.identifier.otherScopus: 85092551544
dc.identifier.urihttp://hdl.handle.net/10023/20875
dc.descriptionR.B. acknowledges the Netherlands Organization for Scientific Research (NWO) (Vidi 723.012.104). C.S.L. thanks the Leverhulme Trust Early Career Fellowship (ECF‐2018‐480). We also acknowledge the NWO for funding the X‐ray diffractometer used in this study. K.S. acknowledges financial support from The Netherlands Centre for Multiscale Catalytic Energy Conversion (MCEC).en
dc.description.abstractA novel route for the production of the versatile chemical building block phthalide from biorenewable furfuryl alcohol and acrylate esters is presented. Two challenges that limit sustainable aromatics production via Diels–Alder (DA) aromatisation—an unfavourable equilibrium position and undesired regioselectivity when using asymmetric addends—were addressed using a dynamic kinetic trapping strategy. Activated acrylates were used to speed up the forward and reverse DA reactions, allowing for one of the four DA adducts to undergo a selective intramolecular lactonisation reaction in the presence of a weak base. The adduct is removed from the equilibrium pool, pulling the system completely to the product with a fixed, desired regiochemistry. A single 1,2-regioisomeric lactone product was formed in up to 86 % yield and the acrylate activating agent liberated for reuse. The lactone was aromatised to give phthalide in almost quantitative yield in the presence of Ac2O and a catalytic amount of strong acid, or in 79 % using only catalytic acid.
dc.format.extent6
dc.language.isoeng
dc.relation.ispartofAngewandte Chemie - International Editionen
dc.rightsCopyright © 2020 The Authors. Published by Wiley-VCH GmbH. This is an open access article under the terms of the Creative Commons Attribution‐NonCommercial‐NoDerivs License, which permits use and distribution in any medium, provided the original work is properly cited, the use is non‐commercial and no modifications or adaptations are made.en
dc.subjectBiomassen
dc.subjectDehydrationen
dc.subjectDiels–Alder reactionsen
dc.subjectLactonisationen
dc.subjectSustainable chemistryen
dc.subjectQD Chemistryen
dc.subjectCatalysisen
dc.subjectChemistry(all)en
dc.subjectDASen
dc.subject.lccQDen
dc.titleDynamic trapping as a selective route to renewable phthalide from biomass-derived furfuryl alcoholen
dc.typeJournal articleen
dc.description.versionPublisher PDFen
dc.contributor.institutionUniversity of St Andrews.School of Chemistryen
dc.identifier.doihttps://doi.org/10.1002/anie.202009001
dc.description.statusPeer revieweden


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