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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| Formato: | Tesis |
| Lenguaje: | English |
| Publicado: |
2016
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| _version_ | 1826306962331009024 |
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| author | Verhoog, S |
| author2 | Gouverneur, V |
| author_facet | Gouverneur, V Verhoog, S |
| author_sort | Verhoog, S |
| collection | OXFORD |
| description | <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> |
| first_indexed | 2024-03-07T06:55:52Z |
| format | Thesis |
| id | oxford-uuid:fe1f95b5-502e-4bf8-b12c-6c2fb1bc03c0 |
| institution | University of Oxford |
| language | English |
| last_indexed | 2024-03-07T06:55:52Z |
| publishDate | 2016 |
| record_format | dspace |
| spelling | oxford-uuid:fe1f95b5-502e-4bf8-b12c-6c2fb1bc03c02022-03-27T13:33:58ZLate-Stage TrifluoromethylationThesishttp://purl.org/coar/resource_type/c_db06uuid:fe1f95b5-502e-4bf8-b12c-6c2fb1bc03c0EnglishORA Deposit2016Verhoog, SGouverneur, V<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> |
| spellingShingle | Verhoog, S Late-Stage Trifluoromethylation |
| title | Late-Stage Trifluoromethylation |
| title_full | Late-Stage Trifluoromethylation |
| title_fullStr | Late-Stage Trifluoromethylation |
| title_full_unstemmed | Late-Stage Trifluoromethylation |
| title_short | Late-Stage Trifluoromethylation |
| title_sort | late stage trifluoromethylation |
| work_keys_str_mv | AT verhoogs latestagetrifluoromethylation |