Developments in C-H oxidation methodologies

Chapter One of this thesis describes classical oxidation methodologies and the importance of the development of sustainable methodologies. The overall thesis aims are also outlined in relation to this. In Chapter Two, cross-dehydrogenative coupling reactions to form benzylic C-C bonds are investi...

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Main Author: Finney, Laura
Format: Thesis (University of Nottingham only)
Language:English
Published: 2019
Subjects:
Online Access:https://eprints.nottingham.ac.uk/56177/
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author Finney, Laura
author_facet Finney, Laura
author_sort Finney, Laura
building Nottingham Research Data Repository
collection Online Access
description Chapter One of this thesis describes classical oxidation methodologies and the importance of the development of sustainable methodologies. The overall thesis aims are also outlined in relation to this. In Chapter Two, cross-dehydrogenative coupling reactions to form benzylic C-C bonds are investigated with photo-activated 1,4-hydroquinone (BQH2). A review of the relevant literature describes catalytic DDQ oxidations and known CDC reactions. This is followed by our research findings with photo-activated BQH2 in Chapter Three. The use of visible light and BQH2 is extended to the synthesis of benzylic esters in Chapter Four. The protocol employs sub-stoichiometric quantities of BQH2 and copper chloride dihydrate in dimethyl carbonate (DMC) and displays how the natural product arbutin, derived from bearberry (uva-ursi) leaves, may also be used as a sustainable pre-oxidant. The oxidation of unactivated alkanes is discussed in Chapter Five. Discussed are Nature’s approaches, both metal and non-metal mediated to oxidise alkanes. The most common modern synthetic procedures for such transformations are also reviewed as well as previous work by the Moody Group. Chapter Six reports the research findings which focus on the further exploration of the work published by the Moody group, focusing on the use of commercial hydrogen peroxide solutions commonly used in cleaning as an oxidant in the presence of acid. Work has been conducted to optimise existing conditions and further investigate the scope of the reaction. Potential future work in this area is also reported. Chapter Seven contains full experimental details for the described research.
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spelling nottingham-561772025-02-28T14:25:22Z https://eprints.nottingham.ac.uk/56177/ Developments in C-H oxidation methodologies Finney, Laura Chapter One of this thesis describes classical oxidation methodologies and the importance of the development of sustainable methodologies. The overall thesis aims are also outlined in relation to this. In Chapter Two, cross-dehydrogenative coupling reactions to form benzylic C-C bonds are investigated with photo-activated 1,4-hydroquinone (BQH2). A review of the relevant literature describes catalytic DDQ oxidations and known CDC reactions. This is followed by our research findings with photo-activated BQH2 in Chapter Three. The use of visible light and BQH2 is extended to the synthesis of benzylic esters in Chapter Four. The protocol employs sub-stoichiometric quantities of BQH2 and copper chloride dihydrate in dimethyl carbonate (DMC) and displays how the natural product arbutin, derived from bearberry (uva-ursi) leaves, may also be used as a sustainable pre-oxidant. The oxidation of unactivated alkanes is discussed in Chapter Five. Discussed are Nature’s approaches, both metal and non-metal mediated to oxidise alkanes. The most common modern synthetic procedures for such transformations are also reviewed as well as previous work by the Moody Group. Chapter Six reports the research findings which focus on the further exploration of the work published by the Moody group, focusing on the use of commercial hydrogen peroxide solutions commonly used in cleaning as an oxidant in the presence of acid. Work has been conducted to optimise existing conditions and further investigate the scope of the reaction. Potential future work in this area is also reported. Chapter Seven contains full experimental details for the described research. 2019-07-17 Thesis (University of Nottingham only) NonPeerReviewed application/pdf en arr https://eprints.nottingham.ac.uk/56177/1/Laura%20Finney%20Corrected%20Thesis.pdf Finney, Laura (2019) Developments in C-H oxidation methodologies. PhD thesis, University of Nottingham. Oxidation Organic chemistry C-H oxidation
spellingShingle Oxidation
Organic chemistry
C-H oxidation
Finney, Laura
Developments in C-H oxidation methodologies
title Developments in C-H oxidation methodologies
title_full Developments in C-H oxidation methodologies
title_fullStr Developments in C-H oxidation methodologies
title_full_unstemmed Developments in C-H oxidation methodologies
title_short Developments in C-H oxidation methodologies
title_sort developments in c-h oxidation methodologies
topic Oxidation
Organic chemistry
C-H oxidation
url https://eprints.nottingham.ac.uk/56177/