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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...

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Autores principales: Horton, Thomas A. R., Wang, Meng, Shaver, Michael P.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2022
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.
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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
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