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N-Heterocyclic Carbene Silver Complex Modified Polyacrylonitrile Fiber/MIL-101(Cr) Composite as Efficient Chiral Catalyst for Three-Component Coupling Reaction

Complex asymmetric synthesis can be realized by the chiral induction of amino acids in nature. It is of great significance to design a new biomimetic catalytic system for asymmetric synthesis. In this context, we report the preparation and characterization of the composite of polyacrylonitrile fiber...

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Autores principales: Xin, Ningning, Jing, Xuemin, Zhang, Cheng-Gen, Peng, Xiaoxia, Liu, Jing, Wang, Qixing, Wang, Wei, Cao, Jian, Tao, Minli
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2022
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9736975/
https://www.ncbi.nlm.nih.gov/pubmed/36500798
http://dx.doi.org/10.3390/nano12234175
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author Xin, Ningning
Jing, Xuemin
Zhang, Cheng-Gen
Peng, Xiaoxia
Liu, Jing
Wang, Qixing
Wang, Wei
Cao, Jian
Tao, Minli
author_facet Xin, Ningning
Jing, Xuemin
Zhang, Cheng-Gen
Peng, Xiaoxia
Liu, Jing
Wang, Qixing
Wang, Wei
Cao, Jian
Tao, Minli
author_sort Xin, Ningning
collection PubMed
description Complex asymmetric synthesis can be realized by the chiral induction of amino acids in nature. It is of great significance to design a new biomimetic catalytic system for asymmetric synthesis. In this context, we report the preparation and characterization of the composite of polyacrylonitrile fiber (PANF) and metal-organic framework to catalyze the chiral synthesis of propargylamines. A confined microenvironment is established with N-heterocyclic carbene (NHC) silver complex-supported PANF and D-proline-encapsulated MIL-101(Cr). This novel supported catalyst demonstrated high activity in addition to excellent stereoselectivity in the three-component reaction between alkynes, aldehydes, and amines (A3). The regeneration can be realized by adsorption of D-proline again when the stereoselectivity decreases after recycle uses. By regulating the confined microenvironment on the composite, the activity and selectivity of the catalytic system are improved with turnover numbers of up to 2800 and 98% ee. The biomimetic catalytic system to A3 coupling reaction is systematically studied, and the synergistic catalytic mechanism between NHC-Ag and D-proline in the confined microenvironment is revealed.
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spelling pubmed-97369752022-12-11 N-Heterocyclic Carbene Silver Complex Modified Polyacrylonitrile Fiber/MIL-101(Cr) Composite as Efficient Chiral Catalyst for Three-Component Coupling Reaction Xin, Ningning Jing, Xuemin Zhang, Cheng-Gen Peng, Xiaoxia Liu, Jing Wang, Qixing Wang, Wei Cao, Jian Tao, Minli Nanomaterials (Basel) Article Complex asymmetric synthesis can be realized by the chiral induction of amino acids in nature. It is of great significance to design a new biomimetic catalytic system for asymmetric synthesis. In this context, we report the preparation and characterization of the composite of polyacrylonitrile fiber (PANF) and metal-organic framework to catalyze the chiral synthesis of propargylamines. A confined microenvironment is established with N-heterocyclic carbene (NHC) silver complex-supported PANF and D-proline-encapsulated MIL-101(Cr). This novel supported catalyst demonstrated high activity in addition to excellent stereoselectivity in the three-component reaction between alkynes, aldehydes, and amines (A3). The regeneration can be realized by adsorption of D-proline again when the stereoselectivity decreases after recycle uses. By regulating the confined microenvironment on the composite, the activity and selectivity of the catalytic system are improved with turnover numbers of up to 2800 and 98% ee. The biomimetic catalytic system to A3 coupling reaction is systematically studied, and the synergistic catalytic mechanism between NHC-Ag and D-proline in the confined microenvironment is revealed. MDPI 2022-11-24 /pmc/articles/PMC9736975/ /pubmed/36500798 http://dx.doi.org/10.3390/nano12234175 Text en © 2022 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 Article
Xin, Ningning
Jing, Xuemin
Zhang, Cheng-Gen
Peng, Xiaoxia
Liu, Jing
Wang, Qixing
Wang, Wei
Cao, Jian
Tao, Minli
N-Heterocyclic Carbene Silver Complex Modified Polyacrylonitrile Fiber/MIL-101(Cr) Composite as Efficient Chiral Catalyst for Three-Component Coupling Reaction
title N-Heterocyclic Carbene Silver Complex Modified Polyacrylonitrile Fiber/MIL-101(Cr) Composite as Efficient Chiral Catalyst for Three-Component Coupling Reaction
title_full N-Heterocyclic Carbene Silver Complex Modified Polyacrylonitrile Fiber/MIL-101(Cr) Composite as Efficient Chiral Catalyst for Three-Component Coupling Reaction
title_fullStr N-Heterocyclic Carbene Silver Complex Modified Polyacrylonitrile Fiber/MIL-101(Cr) Composite as Efficient Chiral Catalyst for Three-Component Coupling Reaction
title_full_unstemmed N-Heterocyclic Carbene Silver Complex Modified Polyacrylonitrile Fiber/MIL-101(Cr) Composite as Efficient Chiral Catalyst for Three-Component Coupling Reaction
title_short N-Heterocyclic Carbene Silver Complex Modified Polyacrylonitrile Fiber/MIL-101(Cr) Composite as Efficient Chiral Catalyst for Three-Component Coupling Reaction
title_sort n-heterocyclic carbene silver complex modified polyacrylonitrile fiber/mil-101(cr) composite as efficient chiral catalyst for three-component coupling reaction
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9736975/
https://www.ncbi.nlm.nih.gov/pubmed/36500798
http://dx.doi.org/10.3390/nano12234175
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