Use this URL to cite or link to this record in EThOS: | https://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.712045 |
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Title: | Late-stage fluorination and perfluoroalkylation | ||||||
Author: | Ó Dúill, Miriam Leslie |
ISNI:
0000 0004 6062 3373
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Awarding Body: | University of Oxford | ||||||
Current Institution: | University of Oxford | ||||||
Date of Award: | 2015 | ||||||
Availability of Full Text: |
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Abstract: | |||||||
In this thesis new synthetic routes towards perfluorinated compounds are described, as well as their radiolabelling with fluorine-18, with the aim of application in pharmaceutically interesting targets. Part A investigates late-stage fluorination, i.e. retrosynthetic CâF bond disconnections. A silver catalysed electrophilic fluorodecarboxylation of fluorinated carboxylic acids for the formation of difluoromethyl-, trifluoromethyl-, and pentafluoroethylarenes is developed and transferred to a radiochemistry setting using [18F]Selectfluor bis(triflate). Part B explores late-stage perfluoroalkylation via cross-coupling strategies. The use of visible light-mediated ruthenium catalysis is investigated for the radical trifluoromethylation and pentafluoroethylation of vinyl- and alkynylsilanes and alkynes. Finally, the first generally applicable copper-mediated cross-coupling of Ruppert-Prakash-like aryl(tetrafluoroethyl)trimethylsilanes (ArCF2CF2SiMe3) is presented.
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Supervisor: | Gouverneur, Veronique | Sponsor: | Biotechnology and Biological Sciences Research Council | ||||
Qualification Name: | Thesis (Ph.D.) | Qualification Level: | Doctoral | ||||
EThOS ID: | uk.bl.ethos.712045 | DOI: | Not available | ||||
Keywords: | Chemistry, Organic ; Fluorine ; Photocatalysis ; Trifluoromethylation ; 18F Radiochemistry ; Transition Metal Catalysis ; Perfluoroalkylation ; Fluorination | ||||||
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