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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MDPI AG
2022-11-01
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| Series: | Nanomaterials |
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| Online Access: | https://www.mdpi.com/2079-4991/12/23/4175 |
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| author | Ningning Xin Xuemin Jing Cheng-Gen Zhang Xiaoxia Peng Jing Liu Qixing Wang Wei Wang Jian Cao Minli Tao |
| author_facet | Ningning Xin Xuemin Jing Cheng-Gen Zhang Xiaoxia Peng Jing Liu Qixing Wang Wei Wang Jian Cao Minli Tao |
| author_sort | Ningning Xin |
| collection | DOAJ |
| 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. |
| first_indexed | 2024-03-09T17:39:15Z |
| format | Article |
| id | doaj.art-f90453d17f0343bba107f050e039f29b |
| institution | Directory Open Access Journal |
| issn | 2079-4991 |
| language | English |
| last_indexed | 2024-03-09T17:39:15Z |
| publishDate | 2022-11-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Nanomaterials |
| spelling | doaj.art-f90453d17f0343bba107f050e039f29b2023-11-24T11:46:42ZengMDPI AGNanomaterials2079-49912022-11-011223417510.3390/nano12234175N-Heterocyclic Carbene Silver Complex Modified Polyacrylonitrile Fiber/MIL-101(Cr) Composite as Efficient Chiral Catalyst for Three-Component Coupling ReactionNingning Xin0Xuemin Jing1Cheng-Gen Zhang2Xiaoxia Peng3Jing Liu4Qixing Wang5Wei Wang6Jian Cao7Minli Tao8School of Chemistry and Material Science, Langfang Normal University, Langfang 065000, ChinaSchool of Chemistry and Material Science, Langfang Normal University, Langfang 065000, ChinaSchool of Chemistry and Material Science, Langfang Normal University, Langfang 065000, ChinaSchool of Chemistry and Material Science, Langfang Normal University, Langfang 065000, ChinaSchool of Chemistry and Material Science, Langfang Normal University, Langfang 065000, ChinaDepartment of Chemistry, School of Science, Tianjin University, Tianjin 300072, ChinaHebei Diyuan Pharmaceutical Technology Co., Ltd., Cangzhou 061007, ChinaSchool of Chemistry and Material Science, Langfang Normal University, Langfang 065000, ChinaDepartment of Chemistry, School of Science, Tianjin University, Tianjin 300072, ChinaComplex 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.https://www.mdpi.com/2079-4991/12/23/4175carbenescoupling reactionnanoparticlespolyacrylonitrile fibermetal-organic framework |
| spellingShingle | Ningning Xin Xuemin Jing Cheng-Gen Zhang Xiaoxia Peng Jing Liu Qixing Wang Wei Wang Jian Cao Minli Tao N-Heterocyclic Carbene Silver Complex Modified Polyacrylonitrile Fiber/MIL-101(Cr) Composite as Efficient Chiral Catalyst for Three-Component Coupling Reaction Nanomaterials carbenes coupling reaction nanoparticles polyacrylonitrile fiber metal-organic framework |
| 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 | carbenes coupling reaction nanoparticles polyacrylonitrile fiber metal-organic framework |
| url | https://www.mdpi.com/2079-4991/12/23/4175 |
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