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Polymer ionic liquid network: a highly effective reusable catalyst for one-pot synthesis of heterocyclic compounds

Significant efforts have been devoted to developing immobilized chiral catalysts with high activity, selectivity, and stability. In this present study, a new heterogeneous proline catalyst system was prepared based on strong noncovalent interactions between polymer ionic liquid (PIL) and l-proline....

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Autores principales: Li, Xinjuan, Wang, Shangyue, Wang, Kai, Jia, Xianbin, Hu, Zhiguo
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2018
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9092053/
https://www.ncbi.nlm.nih.gov/pubmed/35558415
http://dx.doi.org/10.1039/c8ra08712a
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author Li, Xinjuan
Wang, Shangyue
Wang, Kai
Jia, Xianbin
Hu, Zhiguo
author_facet Li, Xinjuan
Wang, Shangyue
Wang, Kai
Jia, Xianbin
Hu, Zhiguo
author_sort Li, Xinjuan
collection PubMed
description Significant efforts have been devoted to developing immobilized chiral catalysts with high activity, selectivity, and stability. In this present study, a new heterogeneous proline catalyst system was prepared based on strong noncovalent interactions between polymer ionic liquid (PIL) and l-proline. First, pyridine PILs, which can complex with l-proline monomers through noncovalent interactions, were synthesized using reversible addition–fragmentation chain transfer (RAFT) polymerization. The polymer network-supported chiral catalysts were obtained following further free radical polymerization. Different structures were formed in response to different ratios of PIL and chiral monomer, as well as different PIL anions, in the reactions. The new formed layer structures and synergic effects of PIL resulted in heterogeneous catalysts with high catalytic activity and enantioselectivity, thus endowing them with better catalytic performance for the one-pot synthesis of heterocyclic compounds compared to homogeneous catalytic systems. These catalytic systems were able to be reused and recycled five times with no discernible loss in catalytic activity and enantioselectivity. l-Proline was efficiently loaded onto the polymer network simply based on supramolecular interactions, providing a novel method of synthesizing high performance supported catalysts for organic reactions.
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spelling pubmed-90920532022-05-11 Polymer ionic liquid network: a highly effective reusable catalyst for one-pot synthesis of heterocyclic compounds Li, Xinjuan Wang, Shangyue Wang, Kai Jia, Xianbin Hu, Zhiguo RSC Adv Chemistry Significant efforts have been devoted to developing immobilized chiral catalysts with high activity, selectivity, and stability. In this present study, a new heterogeneous proline catalyst system was prepared based on strong noncovalent interactions between polymer ionic liquid (PIL) and l-proline. First, pyridine PILs, which can complex with l-proline monomers through noncovalent interactions, were synthesized using reversible addition–fragmentation chain transfer (RAFT) polymerization. The polymer network-supported chiral catalysts were obtained following further free radical polymerization. Different structures were formed in response to different ratios of PIL and chiral monomer, as well as different PIL anions, in the reactions. The new formed layer structures and synergic effects of PIL resulted in heterogeneous catalysts with high catalytic activity and enantioselectivity, thus endowing them with better catalytic performance for the one-pot synthesis of heterocyclic compounds compared to homogeneous catalytic systems. These catalytic systems were able to be reused and recycled five times with no discernible loss in catalytic activity and enantioselectivity. l-Proline was efficiently loaded onto the polymer network simply based on supramolecular interactions, providing a novel method of synthesizing high performance supported catalysts for organic reactions. The Royal Society of Chemistry 2018-12-19 /pmc/articles/PMC9092053/ /pubmed/35558415 http://dx.doi.org/10.1039/c8ra08712a Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by/3.0/
spellingShingle Chemistry
Li, Xinjuan
Wang, Shangyue
Wang, Kai
Jia, Xianbin
Hu, Zhiguo
Polymer ionic liquid network: a highly effective reusable catalyst for one-pot synthesis of heterocyclic compounds
title Polymer ionic liquid network: a highly effective reusable catalyst for one-pot synthesis of heterocyclic compounds
title_full Polymer ionic liquid network: a highly effective reusable catalyst for one-pot synthesis of heterocyclic compounds
title_fullStr Polymer ionic liquid network: a highly effective reusable catalyst for one-pot synthesis of heterocyclic compounds
title_full_unstemmed Polymer ionic liquid network: a highly effective reusable catalyst for one-pot synthesis of heterocyclic compounds
title_short Polymer ionic liquid network: a highly effective reusable catalyst for one-pot synthesis of heterocyclic compounds
title_sort polymer ionic liquid network: a highly effective reusable catalyst for one-pot synthesis of heterocyclic compounds
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9092053/
https://www.ncbi.nlm.nih.gov/pubmed/35558415
http://dx.doi.org/10.1039/c8ra08712a
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