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A Facile Strategy for the High Yielding, Quantitative Conversion of Polyglycol End-Groups to Amines

Amino end-group functionalised polyglycols are important intermediates in the synthesis of sophisticated polymeric architectures and biomaterials. Herein, we report a facile strategy for the end-group conversion of hydroxyl-terminated polyglycols to amino-terminated polyglycols in high isolated yiel...

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Detalles Bibliográficos
Autores principales: Yan, Jie, Marina, Paula Facal, Blencowe, Anton
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2021
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8123656/
https://www.ncbi.nlm.nih.gov/pubmed/33926044
http://dx.doi.org/10.3390/polym13091403
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author Yan, Jie
Marina, Paula Facal
Blencowe, Anton
author_facet Yan, Jie
Marina, Paula Facal
Blencowe, Anton
author_sort Yan, Jie
collection PubMed
description Amino end-group functionalised polyglycols are important intermediates in the synthesis of sophisticated polymeric architectures and biomaterials. Herein, we report a facile strategy for the end-group conversion of hydroxyl-terminated polyglycols to amino-terminated polyglycols in high isolated yields and with excellent end-group fidelity. Following traditional conversion of polyglycol hydroxyl end-groups to azides via the corresponding mesylate, reduction with zinc in the presence of ammonium chloride afforded a range of amino end-group functionalised poly(ethylene glycol) and poly(propylene glycol) homopolymers and copolymers with isolated yields of 82–99% and end-group conversions of >99% as determined by NMR spectroscopy and MALDI ToF MS. Furthermore, this process is applicable to a sequential reagent addition approach without intermediate polymer isolation steps with only a slight reduction in yield and end-group conversion (95%). Importantly, a simple work-up procedure provides access to high purity polyglycols without contamination from other reagents.
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spelling pubmed-81236562021-05-16 A Facile Strategy for the High Yielding, Quantitative Conversion of Polyglycol End-Groups to Amines Yan, Jie Marina, Paula Facal Blencowe, Anton Polymers (Basel) Communication Amino end-group functionalised polyglycols are important intermediates in the synthesis of sophisticated polymeric architectures and biomaterials. Herein, we report a facile strategy for the end-group conversion of hydroxyl-terminated polyglycols to amino-terminated polyglycols in high isolated yields and with excellent end-group fidelity. Following traditional conversion of polyglycol hydroxyl end-groups to azides via the corresponding mesylate, reduction with zinc in the presence of ammonium chloride afforded a range of amino end-group functionalised poly(ethylene glycol) and poly(propylene glycol) homopolymers and copolymers with isolated yields of 82–99% and end-group conversions of >99% as determined by NMR spectroscopy and MALDI ToF MS. Furthermore, this process is applicable to a sequential reagent addition approach without intermediate polymer isolation steps with only a slight reduction in yield and end-group conversion (95%). Importantly, a simple work-up procedure provides access to high purity polyglycols without contamination from other reagents. MDPI 2021-04-26 /pmc/articles/PMC8123656/ /pubmed/33926044 http://dx.doi.org/10.3390/polym13091403 Text en © 2021 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Communication
Yan, Jie
Marina, Paula Facal
Blencowe, Anton
A Facile Strategy for the High Yielding, Quantitative Conversion of Polyglycol End-Groups to Amines
title A Facile Strategy for the High Yielding, Quantitative Conversion of Polyglycol End-Groups to Amines
title_full A Facile Strategy for the High Yielding, Quantitative Conversion of Polyglycol End-Groups to Amines
title_fullStr A Facile Strategy for the High Yielding, Quantitative Conversion of Polyglycol End-Groups to Amines
title_full_unstemmed A Facile Strategy for the High Yielding, Quantitative Conversion of Polyglycol End-Groups to Amines
title_short A Facile Strategy for the High Yielding, Quantitative Conversion of Polyglycol End-Groups to Amines
title_sort facile strategy for the high yielding, quantitative conversion of polyglycol end-groups to amines
topic Communication
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8123656/
https://www.ncbi.nlm.nih.gov/pubmed/33926044
http://dx.doi.org/10.3390/polym13091403
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