Design, synthesis and applications of hydroxylmethyl-aryl phosphine oxides in phosphorus catalysis
Organophosphorus-mediated reactions are important tools in organic chemistry and are used in the synthesis of highly desirable drug targets, such as morphine.1 A major drawback of traditional phosphorus-mediated reactions is the formation of stoichiometric amounts of phosphine oxide by-products; thi...
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| Format: | Thesis (University of Nottingham only) |
| Language: | English |
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2015
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| Online Access: | https://eprints.nottingham.ac.uk/30361/ |
| _version_ | 1848793968739876864 |
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| author | Chapman, Charlotte Grace |
| author_facet | Chapman, Charlotte Grace |
| author_sort | Chapman, Charlotte Grace |
| building | Nottingham Research Data Repository |
| collection | Online Access |
| description | Organophosphorus-mediated reactions are important tools in organic chemistry and are used in the synthesis of highly desirable drug targets, such as morphine.1 A major drawback of traditional phosphorus-mediated reactions is the formation of stoichiometric amounts of phosphine oxide by-products; this renders the product purification difficult and reduces the atom efficiency of these transformations. For these reasons, catalytic variants become desirable; there being two potential strategies to achieve the catalysis; i) redox-driven and ii) redox-neutral.2-4 The redox-driven catalytic cycle requires a reductant for the turnover whilst the redox-neutral system uses a sacrificial reagent to directly turn over the phosphine oxide to the active phosphorus (V) reagent. This thesis will report upon a new class of Hydroxylmethyl-Aryl phosphine 1 and phosphine oxide 3 catalyst for use in a redox-driven catalytic reaction; the Staudinger reduction Scheme 1, and routes to a potential redox-neutral catalytic Mitsunobu reaction Scheme 2. |
| first_indexed | 2025-11-14T19:08:44Z |
| format | Thesis (University of Nottingham only) |
| id | nottingham-30361 |
| institution | University of Nottingham Malaysia Campus |
| institution_category | Local University |
| language | English |
| last_indexed | 2025-11-14T19:08:44Z |
| publishDate | 2015 |
| recordtype | eprints |
| repository_type | Digital Repository |
| spelling | nottingham-303612025-02-28T13:20:45Z https://eprints.nottingham.ac.uk/30361/ Design, synthesis and applications of hydroxylmethyl-aryl phosphine oxides in phosphorus catalysis Chapman, Charlotte Grace Organophosphorus-mediated reactions are important tools in organic chemistry and are used in the synthesis of highly desirable drug targets, such as morphine.1 A major drawback of traditional phosphorus-mediated reactions is the formation of stoichiometric amounts of phosphine oxide by-products; this renders the product purification difficult and reduces the atom efficiency of these transformations. For these reasons, catalytic variants become desirable; there being two potential strategies to achieve the catalysis; i) redox-driven and ii) redox-neutral.2-4 The redox-driven catalytic cycle requires a reductant for the turnover whilst the redox-neutral system uses a sacrificial reagent to directly turn over the phosphine oxide to the active phosphorus (V) reagent. This thesis will report upon a new class of Hydroxylmethyl-Aryl phosphine 1 and phosphine oxide 3 catalyst for use in a redox-driven catalytic reaction; the Staudinger reduction Scheme 1, and routes to a potential redox-neutral catalytic Mitsunobu reaction Scheme 2. 2015-12-11 Thesis (University of Nottingham only) NonPeerReviewed application/pdf en arr https://eprints.nottingham.ac.uk/30361/1/Thesis%20Final.pdf Chapman, Charlotte Grace (2015) Design, synthesis and applications of hydroxylmethyl-aryl phosphine oxides in phosphorus catalysis. PhD thesis, University of Nottingham. Phosphorus catalysis |
| spellingShingle | Phosphorus catalysis Chapman, Charlotte Grace Design, synthesis and applications of hydroxylmethyl-aryl phosphine oxides in phosphorus catalysis |
| title | Design, synthesis and applications of hydroxylmethyl-aryl phosphine oxides in phosphorus catalysis |
| title_full | Design, synthesis and applications of hydroxylmethyl-aryl phosphine oxides in phosphorus catalysis |
| title_fullStr | Design, synthesis and applications of hydroxylmethyl-aryl phosphine oxides in phosphorus catalysis |
| title_full_unstemmed | Design, synthesis and applications of hydroxylmethyl-aryl phosphine oxides in phosphorus catalysis |
| title_short | Design, synthesis and applications of hydroxylmethyl-aryl phosphine oxides in phosphorus catalysis |
| title_sort | design, synthesis and applications of hydroxylmethyl-aryl phosphine oxides in phosphorus catalysis |
| topic | Phosphorus catalysis |
| url | https://eprints.nottingham.ac.uk/30361/ |