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dc.contributor.authorIsmael, Aya
dc.contributor.authorSkrydstrup, Troels
dc.contributor.authorBayer, Annette
dc.date.accessioned2020-05-06T06:49:02Z
dc.date.available2020-05-06T06:49:02Z
dc.date.issued2020-02-10
dc.description.abstractWe have developed a carbonylative approach to the synthesis of diversely substituted 2-aroylbenzoate esters featuring a new protocol for the carbonylative coupling of aryl bromides with boronic acids and a new strategy to favour carbonylative over non-carbonylative reactions. Two different synthetic pathways – (i) the alkoxycarbonylation of 2-bromo benzophenones and (ii) the carbonylative Suzuki–Miyaura coupling of 2-bromobenzoate esters – were evaluated. The latter approach provided a broader substrate tolerance, and thus was the preferred pathway. We observed that 2-substituted aryl bromides were challenging substrates for carbonylative chemistry favouring the non-carbonylative pathway. However, we found that carbonylative Suzuki–Miyaura couplings can be improved by slow addition of the boronic acid, suppressing the unwanted direct Suzuki coupling and, thus increasing the yield of the carbonylative reaction.en_US
dc.identifier.citationIsmael A, Skrydstrup T, Bayer A. Carbonylative Suzuki-Miyaura couplings of sterically hindered aryl halides: Synthesis of 2-aroylbenzoate derivatives. Organic and biomolecular chemistry. 2020en_US
dc.identifier.cristinIDFRIDAID 1790483
dc.identifier.doi10.1039/D0OB00044B
dc.identifier.issn1477-0520
dc.identifier.issn1477-0539
dc.identifier.urihttps://hdl.handle.net/10037/18225
dc.language.isoengen_US
dc.publisherRoyal Society of Chemistryen_US
dc.relation.ispartofIsmael, A. (2020). Method development towards synthesis of carbapenemase inhibitors. (Doctoral thesis). <a href=https://hdl.handle.net/10037/19594>https://hdl.handle.net/10037/19594</a>.
dc.relation.journalOrganic and biomolecular chemistry
dc.relation.projectIDNordforsk: 85378en_US
dc.rights.accessRightsopenAccessen_US
dc.rights.holder© The Royal Society of Chemistry 2020en_US
dc.subjectVDP::Mathematics and natural science: 400::Chemistry: 440en_US
dc.subjectVDP::Matematikk og Naturvitenskap: 400::Kjemi: 440en_US
dc.titleCarbonylative Suzuki-Miyaura couplings of sterically hindered aryl halides: Synthesis of 2-aroylbenzoate derivativesen_US
dc.type.versionacceptedVersionen_US
dc.typeJournal articleen_US
dc.typeTidsskriftartikkelen_US
dc.typePeer revieweden_US


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