Late-Stage Trifluoromethylation
<p>This thesis is concerned with the development of methodology for late-stage trifluoromethylation of complex molecules.</p> <p><strong>Chapter 1</strong> introduces the concept of late-stage trifluoromethylations and details the effect that substitution of a CF<sub...
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| Format: | Abschlussarbeit |
| Sprache: | English |
| Veröffentlicht: |
2016
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| Zusammenfassung: | <p>This thesis is concerned with the development of methodology for late-stage trifluoromethylation of complex molecules.</p> <p><strong>Chapter 1</strong> introduces the concept of late-stage trifluoromethylations and details the effect that substitution of a CF<sub>3</sub> group can have on the properties of organic molecules. Methods for generating reactive trifluoromethylating intermediates for use in allylic and aliphatic trifluoromethylation are also discussed.</p> <p><strong>Chapter 2</strong> examines the photoredox catalysis as a mechanistic manifold for the trifluoromethylation of allylsilanes for the synthesis of branched allylic trifluoromethylated compounds. The stereogenic trifluoromethylation of enantio-enriched allylsilanes through chirality transfer is explored, and mechanistic experiments are performed to investigate the formation of the CF<sub>3</sub> radical intermediate.</p> <p><strong>Chapter 3</strong> details the development of hydrotrifluoromethylation of terminal alkenes for the synthesis of aliphatic trifluoromethylated compounds under mild conditions using photoredox catalysis. This methodology tolerates a wide range of functional groups and is applicable to the late-stage trifluoromethylation of complex organic compounds.</p> <p><strong>Chapter 4</strong> explores the synthesis and isolation of <sup>18</sup>F-labelled aryl -SCF<sub>3</sub>, -OCF<sub>3</sub> and - OCF2H compounds from high specific activity [<sup>18</sup>F]fluoride, using Ag(I) mediated halogen exchange as a mode of activation. This methodology can be used for the synthesis and isolation of <sup>18</sup>F labelled radiotracers containing new functional groups that have interesting biological and pharmacological properties.</p> <p><strong>Chapter 5</strong> contains full experimental procedures and characterisation data for compounds synthesised in chapters 2, 3 and 4.</p> |
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