Novel catalytic hydrosilane mediated reduction reactions
This thesis starts with an introduction to the relevant organosilicon and reduction chemistry concepts that underpin the chemistry that is explored in later chapters. In particular, hyperconjugation, relevant organosilicon reagent classes and reduction of carbonyl containing compounds are explored....
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| Format: | Thesis (University of Nottingham only) |
| Language: | English |
| Published: |
2021
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| Online Access: | https://eprints.nottingham.ac.uk/64543/ |
| _version_ | 1848800141578862592 |
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| author | Stoll, Emma |
| author_facet | Stoll, Emma |
| author_sort | Stoll, Emma |
| building | Nottingham Research Data Repository |
| collection | Online Access |
| description | This thesis starts with an introduction to the relevant organosilicon and reduction chemistry concepts that underpin the chemistry that is explored in later chapters. In particular, hyperconjugation, relevant organosilicon reagent classes and reduction of carbonyl containing compounds are explored.
Chapter one describes a reductive amination reaction with carboxylic acids in lieu of lower oxidation state alternatives such as aldehydes or alkyl halides. A two-step reaction process is described, whereby the dual reactivity of phenylsilane is exploited in an initial amidation followed by a zinc acetate-catalysed amide reduction. The reaction is applicable to a wide range of substrates and several potential applications have been explored, as well as mechanistic studies.
Chapter two builds on the utility of the novel zinc acetate / phenylsilane reduction system for the reduction of carboxylic acids to the corresponding alcohols. However, this time employing the use of zinc acetate and N-methyl morpholine in a dual catalytic system. The protocol is applicable to a wide range of substrates and proceeds via activation using hydrosilanes. Mechanistic studies have also been undertaken to gain insights into the reaction mechanism. |
| first_indexed | 2025-11-14T20:46:51Z |
| format | Thesis (University of Nottingham only) |
| id | nottingham-64543 |
| institution | University of Nottingham Malaysia Campus |
| institution_category | Local University |
| language | English |
| last_indexed | 2025-11-14T20:46:51Z |
| publishDate | 2021 |
| recordtype | eprints |
| repository_type | Digital Repository |
| spelling | nottingham-645432025-02-28T15:11:15Z https://eprints.nottingham.ac.uk/64543/ Novel catalytic hydrosilane mediated reduction reactions Stoll, Emma This thesis starts with an introduction to the relevant organosilicon and reduction chemistry concepts that underpin the chemistry that is explored in later chapters. In particular, hyperconjugation, relevant organosilicon reagent classes and reduction of carbonyl containing compounds are explored. Chapter one describes a reductive amination reaction with carboxylic acids in lieu of lower oxidation state alternatives such as aldehydes or alkyl halides. A two-step reaction process is described, whereby the dual reactivity of phenylsilane is exploited in an initial amidation followed by a zinc acetate-catalysed amide reduction. The reaction is applicable to a wide range of substrates and several potential applications have been explored, as well as mechanistic studies. Chapter two builds on the utility of the novel zinc acetate / phenylsilane reduction system for the reduction of carboxylic acids to the corresponding alcohols. However, this time employing the use of zinc acetate and N-methyl morpholine in a dual catalytic system. The protocol is applicable to a wide range of substrates and proceeds via activation using hydrosilanes. Mechanistic studies have also been undertaken to gain insights into the reaction mechanism. 2021-07-31 Thesis (University of Nottingham only) NonPeerReviewed application/pdf en cc_by https://eprints.nottingham.ac.uk/64543/1/Corrected%20Thesis.pdf Stoll, Emma (2021) Novel catalytic hydrosilane mediated reduction reactions. PhD thesis, University of Nottingham. Novel catalytic hydrosilane |
| spellingShingle | Novel catalytic hydrosilane Stoll, Emma Novel catalytic hydrosilane mediated reduction reactions |
| title | Novel catalytic hydrosilane mediated reduction reactions |
| title_full | Novel catalytic hydrosilane mediated reduction reactions |
| title_fullStr | Novel catalytic hydrosilane mediated reduction reactions |
| title_full_unstemmed | Novel catalytic hydrosilane mediated reduction reactions |
| title_short | Novel catalytic hydrosilane mediated reduction reactions |
| title_sort | novel catalytic hydrosilane mediated reduction reactions |
| topic | Novel catalytic hydrosilane |
| url | https://eprints.nottingham.ac.uk/64543/ |