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dc.contributor.authorKringlen, Hilde Dalshov
dc.date.accessioned2016-08-17T15:16:29Z
dc.date.available2016-08-17T15:16:29Z
dc.date.issued2016-06-02
dc.date.submitted2016-06-02eng
dc.identifier.urihttps://hdl.handle.net/1956/12624
dc.description.abstractRecently disclosed silver N-heterocyclic carbene complexes holding 4-alkylated imidazoles have been proved to hold cytotoxic properties. In this work, derivatives of such alkylated imidazoles were synthesised to be complexed with silver(I). N,N-diphenyl-4-methylimidazolium teterafluoroborate was synthesised by means of a two step synthetic pathway. The synthesis involved a selective N1-arylation of 4-methyl-1H- imidazole using the palladium-catalysed Buchwald N-arylation method, followed by a direct quaternisation using phenylboronic acid. A 2^2 factorial design was initiated to investigate how the reaction temperature and reaction time influenced the conversion of the starting material. No clear correlation was found, and a full conversion of the starting material was not obtained. The formation of the product was confirmed by LC-MS, but a successful isolation was not achieved. A N,N-diphenyl-4-heptylimidazolium tetrafluoroborate synthesis was attempted by means of a seven/eight step synthetic pathway. The synthesis involved a selective iodination of an imidazole backbone, followed by an altering of the electronic properties by the introduction of an auxiliary group. A first attempt of implementing this step using flow chemistry was successfully performed. The backbone iodide was replaced in a Sonogashira coupling reaction, in which the installed alkyne moiety was reduced using gaseous hydrogen in the presence of Pearlman's catalyst. An attempt of reducing the alkyne moiety using indium as the reducing agent was carried out, without furnishing the desired product. The palladium-catalysed Buchwald method was used to perform an N1-arylation, before phenylboronic acid was utilised in an attempt to obtain the quaternised imidazole. Only traces of the desired product were observed. It is thought that the imidazole side chain constitutes a steric hindrance that reduces the conversion of the starting material.en_US
dc.format.extent2999984 byteseng
dc.format.mimetypeapplication/pdfeng
dc.language.isoengeng
dc.publisherThe University of Bergenen_US
dc.subjectNHCeng
dc.subjectcarbeneeng
dc.subjectcytotoxiceng
dc.subjectimidazoleeng
dc.subject4-iodoimidazoleeng
dc.subjectSonogashiraeng
dc.subjectN-arylationeng
dc.titleDevelopment of Methodology for the Synthesis of Cytotoxic NHC-Ag-Complexesen_US
dc.typeMaster thesis
dc.rights.holderCopyright the Author. All rights reserveden_US
dc.description.localcodeMAMN-KJEM
dc.description.localcodeKJEM399K
dc.subject.nus752299eng
fs.subjectcodeKJEM399K


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