Investigation of Recyclable Palladium Catalysts in C(sp3)–H Acetoxylation and Their Application in a One-Pot Redox-Relay Heck/Reductive Amination Sequence
The use of palladium as a catalyst enables the facile production of pharmaceutical and agrochemical compounds that enhance and sustain our lives. The extraordinary utility of this metal, however, is counterbalanced by its relative scarcity and challenged supply chain, leading to fluctuations in its...
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| Format: | Thesis (University of Nottingham only) |
| Language: | English English |
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2024
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| Online Access: | https://eprints.nottingham.ac.uk/77549/ |
| _version_ | 1848801009174839296 |
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| author | Butler, Thomas James |
| author_facet | Butler, Thomas James |
| author_sort | Butler, Thomas James |
| building | Nottingham Research Data Repository |
| collection | Online Access |
| description | The use of palladium as a catalyst enables the facile production of pharmaceutical and agrochemical compounds that enhance and sustain our lives. The extraordinary utility of this metal, however, is counterbalanced by its relative scarcity and challenged supply chain, leading to fluctuations in its value and uncertainty regarding its long-term availability. This thesis discusses laboratory-scale methods for the recovery and re-use of palladium catalysts supported on carbonaceous solids.
We discuss the application of commercially available palladium on carbon (Pd/C) in the acetoxylation of C(sp3)–H bonds, a transformation that has previously relied upon single-use homogeneous palladium catalysts and bespoke recyclable palladium catalysts that are unavailable for purchase.
The recyclability of Pd/C is investigated, taking into account the release and capture of an active catalyst species during the reaction. Such processes are rarely explored within C–H activation chemistry, allowing for novel insights into the triggers for leaching and deposition processes for this class of reaction.
The use of activated charcoal as a solid support has also been extended to facilitate a one-pot redox-relay Heck/reductive amination procedure towards the synthesis of a library of gamma-aryl propylamines. |
| first_indexed | 2025-11-14T21:00:38Z |
| format | Thesis (University of Nottingham only) |
| id | nottingham-77549 |
| institution | University of Nottingham Malaysia Campus |
| institution_category | Local University |
| language | English English |
| last_indexed | 2025-11-14T21:00:38Z |
| publishDate | 2024 |
| recordtype | eprints |
| repository_type | Digital Repository |
| spelling | nottingham-775492024-07-24T04:41:47Z https://eprints.nottingham.ac.uk/77549/ Investigation of Recyclable Palladium Catalysts in C(sp3)–H Acetoxylation and Their Application in a One-Pot Redox-Relay Heck/Reductive Amination Sequence Butler, Thomas James The use of palladium as a catalyst enables the facile production of pharmaceutical and agrochemical compounds that enhance and sustain our lives. The extraordinary utility of this metal, however, is counterbalanced by its relative scarcity and challenged supply chain, leading to fluctuations in its value and uncertainty regarding its long-term availability. This thesis discusses laboratory-scale methods for the recovery and re-use of palladium catalysts supported on carbonaceous solids. We discuss the application of commercially available palladium on carbon (Pd/C) in the acetoxylation of C(sp3)–H bonds, a transformation that has previously relied upon single-use homogeneous palladium catalysts and bespoke recyclable palladium catalysts that are unavailable for purchase. The recyclability of Pd/C is investigated, taking into account the release and capture of an active catalyst species during the reaction. Such processes are rarely explored within C–H activation chemistry, allowing for novel insights into the triggers for leaching and deposition processes for this class of reaction. The use of activated charcoal as a solid support has also been extended to facilitate a one-pot redox-relay Heck/reductive amination procedure towards the synthesis of a library of gamma-aryl propylamines. 2024-07-24 Thesis (University of Nottingham only) NonPeerReviewed application/pdf en cc_by https://eprints.nottingham.ac.uk/77549/1/Thomas%20Butler%2014247692%20Corrected%20Thesis.pdf application/pdf en cc_by https://eprints.nottingham.ac.uk/77549/2/Copies%20of%20NMR%20Spectra.pdf Butler, Thomas James (2024) Investigation of Recyclable Palladium Catalysts in C(sp3)–H Acetoxylation and Their Application in a One-Pot Redox-Relay Heck/Reductive Amination Sequence. PhD thesis, University of Nottingham. Palladium Catalysis Organic Chemistry C-H Activation Acetoxylation Homogeneous Heterogeneous Capture Release Redox-Relay Heck aryl-propylamine |
| spellingShingle | Palladium Catalysis Organic Chemistry C-H Activation Acetoxylation Homogeneous Heterogeneous Capture Release Redox-Relay Heck aryl-propylamine Butler, Thomas James Investigation of Recyclable Palladium Catalysts in C(sp3)–H Acetoxylation and Their Application in a One-Pot Redox-Relay Heck/Reductive Amination Sequence |
| title | Investigation of Recyclable Palladium Catalysts in C(sp3)–H Acetoxylation and Their Application in a One-Pot Redox-Relay Heck/Reductive Amination Sequence |
| title_full | Investigation of Recyclable Palladium Catalysts in C(sp3)–H Acetoxylation and Their Application in a One-Pot Redox-Relay Heck/Reductive Amination Sequence |
| title_fullStr | Investigation of Recyclable Palladium Catalysts in C(sp3)–H Acetoxylation and Their Application in a One-Pot Redox-Relay Heck/Reductive Amination Sequence |
| title_full_unstemmed | Investigation of Recyclable Palladium Catalysts in C(sp3)–H Acetoxylation and Their Application in a One-Pot Redox-Relay Heck/Reductive Amination Sequence |
| title_short | Investigation of Recyclable Palladium Catalysts in C(sp3)–H Acetoxylation and Their Application in a One-Pot Redox-Relay Heck/Reductive Amination Sequence |
| title_sort | investigation of recyclable palladium catalysts in c(sp3)–h acetoxylation and their application in a one-pot redox-relay heck/reductive amination sequence |
| topic | Palladium Catalysis Organic Chemistry C-H Activation Acetoxylation Homogeneous Heterogeneous Capture Release Redox-Relay Heck aryl-propylamine |
| url | https://eprints.nottingham.ac.uk/77549/ |