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Polymer-supported reducing and oxidising reagents

Polymer-supported reducing and oxidising reagents
Polymer-supported reducing and oxidising reagents

Polymer-supported reagents have the potential to yield very clean product with no purification needed. Solid-supported silane reagents were studied for the reduction of ester to the corresponding aldehyde or ketone. A commercially PS-DES resin was tested in the catch and release reduction of ester. A new silane resin was successfully synthesised in two steps. Unfortunately, an efficient procedure could not be found to perform the first part of the reduction, the hydrosilylation. A protocol for the Tamao-Fleming oxidation was then devised with the new silane resin as its main reagent. Again the hydrosilylation of alkene seemed to be the limiting step. Several polymer-bound IBX derivatives were then synthesised. The oxidation of alcohols proved to be successful despite a modest loading of the first IBX resin. Finally, an efficient three step synthesis of an IBX amide resin with a good loading and reactivity comparable to IBX was devised. A very good method to remove all trace of tetrabutylammonium species from the IBX resins was discovered.

University of Southampton
Lecarpentier, Patrick
cc040af5-614c-45e9-bc64-8b14cde34e8e
Lecarpentier, Patrick
cc040af5-614c-45e9-bc64-8b14cde34e8e

Lecarpentier, Patrick (2006) Polymer-supported reducing and oxidising reagents. University of Southampton, Doctoral Thesis.

Record type: Thesis (Doctoral)

Abstract

Polymer-supported reagents have the potential to yield very clean product with no purification needed. Solid-supported silane reagents were studied for the reduction of ester to the corresponding aldehyde or ketone. A commercially PS-DES resin was tested in the catch and release reduction of ester. A new silane resin was successfully synthesised in two steps. Unfortunately, an efficient procedure could not be found to perform the first part of the reduction, the hydrosilylation. A protocol for the Tamao-Fleming oxidation was then devised with the new silane resin as its main reagent. Again the hydrosilylation of alkene seemed to be the limiting step. Several polymer-bound IBX derivatives were then synthesised. The oxidation of alcohols proved to be successful despite a modest loading of the first IBX resin. Finally, an efficient three step synthesis of an IBX amide resin with a good loading and reactivity comparable to IBX was devised. A very good method to remove all trace of tetrabutylammonium species from the IBX resins was discovered.

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Published date: 2006

Identifiers

Local EPrints ID: 466805
URI: http://eprints.soton.ac.uk/id/eprint/466805
PURE UUID: 67f10c8b-f3bf-4030-90da-9d4d8d246368

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Date deposited: 05 Jul 2022 06:43
Last modified: 16 Mar 2024 20:51

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Contributors

Author: Patrick Lecarpentier

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