The arylation of 2-pyrones and related heterocycles

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dc.check.embargoformatApply the embargo to the e-thesis on CORA (If you have submitted an e-thesis and want to embargo it on CORA)en
dc.check.entireThesisEntire Thesis Restricted
dc.check.opt-outNoen
dc.check.reasonNot applicableen
dc.contributor.advisorMcglacken, Gerard P.en
dc.contributor.authorPrendergast, Aisling M.
dc.contributor.funderScience Foundation Irelanden
dc.date.accessioned2018-05-10T10:34:49Z
dc.date.issued2018
dc.date.submitted2018
dc.description.abstract2-Pyrones, and related heterocycles such as 2-pyridones, 2-coumarins and 2- quinolones, are useful model substrates to test a novel methodology due to their varied chemical properties. In addition, these moieties possess broad spectrum biological activity. Chapter 1 provides a review of C–H activation methodology as it has been applied to 2-pyrones and related heterocycles. Direct arylation via C–H activation of 2-pyrone, 2-pyridone and 2-coumarin compounds is described in Chapter 2. Protocols for the palladium-catalysed direct arylation of these molecules were developed and applied to a library of substrates. C–H activation at both the C–3 and C–5 positions of the 2-pyrone scaffold was achieved. The C–5 direct arylation methodology proceeded with retention of a C–Cl bond to give a cyclised 3-chloro-2-pyrone. In Chapter 3, the development of cross-coupling conditions for the cyclised 3-chloro-2-pyrone is discussed. Following on from this, more generally applicable, environmentally friendly cross-coupling conditions evolved to allow the application of green chemistry principles to the Suzuki-Miyaura cross-coupling of 2-coumarins, 2-pyrones, 2-pyridones and 2-quinolones, with yields of up to 99%. In parallel to the synthetic aspects of this project, investigations were also performed to understand the mechanisms through which 2-coumarins and related heterocycles undergo C–H activation and direct arylation reactions. In Chapter 4 the experiments which were performed as part of these investigations are described, and the results are presented. Based upon these results from three different sets of reaction conditions, it was proposed that C–H activation of these substrates occurs via concerted metallation-deprotonation.en
dc.description.statusNot peer revieweden
dc.description.versionAccepted Version
dc.format.mimetypeapplication/pdfen
dc.identifier.citationPrendergast, A. M. 2018. The arylation of 2-pyrones and related heterocycles. PhD Thesis, University College Cork.en
dc.identifier.endpage275en
dc.identifier.urihttps://hdl.handle.net/10468/6056
dc.language.isoenen
dc.publisherUniversity College Corken
dc.relation.projectinfo:eu-repo/grantAgreement/SFI/SFI Investigator Programme/12/IP/1315/IE/The Direct Arylation of Pyrones, Coumarins, Pyridones and Quinolones/en
dc.rights© 2018, Aisling M. Prendergast.en
dc.rights.urihttp://creativecommons.org/licenses/by-nc-nd/3.0/en
dc.subject2-pyronesen
dc.subject2-pyridonesen
dc.subject2-quinolonesen
dc.subjectC-H activationen
dc.subjectSuzuki-Miyauraen
dc.subjectOrganic chemistryen
dc.subjectDirect arylationen
dc.subjectCoumarinsen
dc.thesis.opt-outfalse
dc.titleThe arylation of 2-pyrones and related heterocyclesen
dc.typeDoctoral thesisen
dc.type.qualificationlevelDoctoralen
dc.type.qualificationnamePhDen
ucc.workflow.supervisorg.mcglacken@ucc.ie
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