This thesis focuses on the development of a novel nucleophilic <sup>18</sup>F-fluorination of (hetero)arenes and of a rapid screening experiment to facilitate the application of this reaction to complex heterocyclic targets of medicinal importance. <strong>Chapter 1</strong> introduces the use of molecules labelled with fluorine-18 as tracers in positron emission tomography and reviews methods for the preparation of [<sup>18</sup>F]fluoroarenes published prior to the start of the work in this thesis. <strong>Chapter 2</strong> describes the development of a novel method for the preparation of electronically-diverse [<sup>18</sup>F]fluoroarenes from aryl boronic esters and [<sup>18</sup>F]fluoride, mediated by a copper complex. Application of this <sup>18</sup>F-fluorodeboronation to electron-rich radiotracers is demonstrated. Methods for the preparation of [<sup>18</sup>F]fluoroarenes published after the start of the work in this thesis are reviewed. <strong>Chapter 3</strong> outlines a rapid screening experiment for assessing the tolerance of the <sup>18</sup>F-fluorodeboronation towards heterocycles, and the use of this method to guide the retro-radiosynthesis of heterocycle-rich, medicinally relevant molecules. <strong>Chapter 4</strong> contains synthetic procedures and characterisation data for compounds in Chapters 2 and 3.
| Identifer | oai:union.ndltd.org:bl.uk/oai:ethos.bl.uk:748746 |
| Date | January 2017 |
| Creators | Taylor, Nicholas J. |
| Contributors | Gouverneur, Véronique |
| Publisher | University of Oxford |
| Source Sets | Ethos UK |
| Detected Language | English |
| Type | Electronic Thesis or Dissertation |
| Source | http://ora.ox.ac.uk/objects/uuid:3fbaaf65-a9a0-4522-8310-6acf29e3ff7c |
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