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Chapter 1 – Introduction briefly introduces the fundamental principles of positron emission tomography (PET). The different isotopes commonly employed in PET are compared, before examples of fluorine-18 (F-18) radiotracers are presented. Various concepts in F-18 radiochemistry are then discussed, including methods for the production of F-18. Key developments in methods for 18F-labelling small molecules are then presented. Finally, the aims of this thesis are summarised. Chapter 2 – Palladium-Catalysed C–O Cross-Coupling and Applications in 18F-Radiochemistry presents the optimisation and scope of a palladium-catalysed C–O cross-coupling between aryl halides and fluorinated alcohols to prepare fluorinated alkyl aryl ethers. Application of the reaction in 18F-radiochemistry is also presented, including a novel radiosynthesis of [18F]trifluoroethanol, and subsequent palladium-mediated cross-coupling with aryl bromides. Chapter 3 – Preparation of [18F]Selectfluor from [18F]Fluoride presents work aimed at preparing [18F]Selectfluor bis(triflate) from [18F]fluoride. This research comprises studies of the synthesis of [18F]xenon difluoride from [18F]fluoride, and subsequent reaction with monoquaternised 1,4-diazabicyclo[2.2.2]octane salts to afford [18F]Selectfluor bis(triflate) and related F-TEDA reagents. The characterisation of [18F]Selectfluor bis(triflate) and a preliminary application of the reagent are also described. Chapter 4 – 18F-Fluorodecarboxylation for Preparing 18F-Labelled Geminal-Difluoro Compounds presents the preliminary investigations into use of [18F]Selectfluor bis (triflate) and [18F]xenon difluoride for the 18F-fluorodecarboxylation of α-fluorinated carboxylic acids to prepare 18F-labelled geminal-difluoro compounds. The development of a more efficient method using [18F]fluoride and a manganese mediator is then presented, along with a preliminary reaction scope.