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Title: Late-stage fluorination and perfluoroalkylation
Author: Ó Dúill, Miriam Leslie
ISNI:       0000 0004 6062 3373
Awarding Body: University of Oxford
Current Institution: University of Oxford
Date of Award: 2015
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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 C–F 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.
Supervisor: Gouverneur, Veronique Sponsor: Biotechnology and Biological Sciences Research Council
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available
Keywords: Chemistry, Organic ; Fluorine ; Photocatalysis ; Trifluoromethylation ; 18F Radiochemistry ; Transition Metal Catalysis ; Perfluoroalkylation ; Fluorination