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Polymeric frustrated Lewis pairs in CO(2)/cyclic ether coupling catalysis
Frustrated Lewis pairs (FLPs) are now ubiquitous as metal-free catalysts in an array of different chemical transformations. In this paper we show that this reactivity can be transferred to a polymeric system, offering advantageous opportunities at the interface between catalysis and stimuli-responsi...
Autores principales: | , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
The Royal Society of Chemistry
2022
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8966658/ https://www.ncbi.nlm.nih.gov/pubmed/35432910 http://dx.doi.org/10.1039/d2sc00894g |
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author | Horton, Thomas A. R. Wang, Meng Shaver, Michael P. |
author_facet | Horton, Thomas A. R. Wang, Meng Shaver, Michael P. |
author_sort | Horton, Thomas A. R. |
collection | PubMed |
description | Frustrated Lewis pairs (FLPs) are now ubiquitous as metal-free catalysts in an array of different chemical transformations. In this paper we show that this reactivity can be transferred to a polymeric system, offering advantageous opportunities at the interface between catalysis and stimuli-responsive materials. Formation of cyclic carbonates from cyclic ethers using CO(2) as a C(1) feedstock continues to be dominated by metal-based systems. When paired with a suitable nucleophile, discrete aryl or alkyl boranes have shown significant promise as metal-free Lewis acidic alternatives, although catalyst reuse remains illusive. Herein, we leverage the reactivity of FLPs in a polymeric system to promote CO(2)/cyclic ether coupling catalysis that can be tuned for the desired epoxide or oxetane substrate. Moreover, these macromolecular FLPs can be reused across multiple reaction cycles, further increasing their appeal over analogous small molecule systems. |
format | Online Article Text |
id | pubmed-8966658 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2022 |
publisher | The Royal Society of Chemistry |
record_format | MEDLINE/PubMed |
spelling | pubmed-89666582022-04-14 Polymeric frustrated Lewis pairs in CO(2)/cyclic ether coupling catalysis Horton, Thomas A. R. Wang, Meng Shaver, Michael P. Chem Sci Chemistry Frustrated Lewis pairs (FLPs) are now ubiquitous as metal-free catalysts in an array of different chemical transformations. In this paper we show that this reactivity can be transferred to a polymeric system, offering advantageous opportunities at the interface between catalysis and stimuli-responsive materials. Formation of cyclic carbonates from cyclic ethers using CO(2) as a C(1) feedstock continues to be dominated by metal-based systems. When paired with a suitable nucleophile, discrete aryl or alkyl boranes have shown significant promise as metal-free Lewis acidic alternatives, although catalyst reuse remains illusive. Herein, we leverage the reactivity of FLPs in a polymeric system to promote CO(2)/cyclic ether coupling catalysis that can be tuned for the desired epoxide or oxetane substrate. Moreover, these macromolecular FLPs can be reused across multiple reaction cycles, further increasing their appeal over analogous small molecule systems. The Royal Society of Chemistry 2022-03-08 /pmc/articles/PMC8966658/ /pubmed/35432910 http://dx.doi.org/10.1039/d2sc00894g Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by/3.0/ |
spellingShingle | Chemistry Horton, Thomas A. R. Wang, Meng Shaver, Michael P. Polymeric frustrated Lewis pairs in CO(2)/cyclic ether coupling catalysis |
title | Polymeric frustrated Lewis pairs in CO(2)/cyclic ether coupling catalysis |
title_full | Polymeric frustrated Lewis pairs in CO(2)/cyclic ether coupling catalysis |
title_fullStr | Polymeric frustrated Lewis pairs in CO(2)/cyclic ether coupling catalysis |
title_full_unstemmed | Polymeric frustrated Lewis pairs in CO(2)/cyclic ether coupling catalysis |
title_short | Polymeric frustrated Lewis pairs in CO(2)/cyclic ether coupling catalysis |
title_sort | polymeric frustrated lewis pairs in co(2)/cyclic ether coupling catalysis |
topic | Chemistry |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8966658/ https://www.ncbi.nlm.nih.gov/pubmed/35432910 http://dx.doi.org/10.1039/d2sc00894g |
work_keys_str_mv | AT hortonthomasar polymericfrustratedlewispairsinco2cyclicethercouplingcatalysis AT wangmeng polymericfrustratedlewispairsinco2cyclicethercouplingcatalysis AT shavermichaelp polymericfrustratedlewispairsinco2cyclicethercouplingcatalysis |