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...

وصف كامل

التفاصيل البيبلوغرافية
المؤلف الرئيسي: Verhoog, S
مؤلفون آخرون: Gouverneur, V
التنسيق: أطروحة
اللغة:English
منشور في: 2016
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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>
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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