4-(N,N-Dimethylamino)pyridine-Embedded Nanoporous Conjugated Polymer as a Highly Active Heterogeneous Organocatalyst
We report herein for the first time the incorporation of a versatile organocatalyst, 4‐(N,N‐dimethylamino)pyridine (DMAP), into the network of a nanoporous conjugated polymer (NCP) by the “bottom‐up” approach. The resulting DMAP‐NCP material possesses highly concentrated and homogeneously distribute...
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| Published in | Chemistry : a European journal Vol. 18; no. 20; pp. 6328 - 6334 |
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| Main Authors | , , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
Weinheim
WILEY-VCH Verlag
14.05.2012
WILEY‐VCH Verlag Wiley Subscription Services, Inc |
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| Abstract | We report herein for the first time the incorporation of a versatile organocatalyst, 4‐(N,N‐dimethylamino)pyridine (DMAP), into the network of a nanoporous conjugated polymer (NCP) by the “bottom‐up” approach. The resulting DMAP‐NCP material possesses highly concentrated and homogeneously distributed DMAP catalytic sites (2.02 mmol g−1). DMAP‐NCP also exhibits enhanced stability and permanent porosity due to the strong covalent linkage and the rigidity of the “bottom‐up” monomers. As a result, DMAP‐NCP shows excellent catalytic activity in the acylation of alcohols with yields of 92–99 %. The DMAP‐NCP catalyst could be easily recovered from the reaction mixture and reused in at least 14 consecutive cycles without measurable loss of activity. Moreover, the catalytic acylation reaction could be performed under neat and continuous‐flow conditions for at least 536 h of continuous work with the same catalyst activity.
Nanoporous catalyst: DMAP‐NCP, a new network nanoporous conjugated polymer containing 4‐(N,N‐dimethylamino)pyridine catalytic moieties, has been constructed by the “bottom‐up” strategy. It shows excellent activity and recyclability in the acylation of alcohols and phenols, even under neat and continuous‐flow conditions (see figure). This study demonstrates the possibility of using DMAP‐NCP as a robust and effective heterogeneous catalyst, especially for practical applications on a large scale. |
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| AbstractList | We report herein for the first time the incorporation of a versatile organocatalyst, 4-(N,N-dimethylamino)pyridine (DMAP), into the network of a nanoporous conjugated polymer (NCP) by the "bottom-up" approach. The resulting DMAP-NCP material possesses highly concentrated and homogeneously distributed DMAP catalytic sites (2.02mmolg-1). DMAP-NCP also exhibits enhanced stability and permanent porosity due to the strong covalent linkage and the rigidity of the "bottom-up" monomers. As a result, DMAP-NCP shows excellent catalytic activity in the acylation of alcohols with yields of 92-99%. The DMAP-NCP catalyst could be easily recovered from the reaction mixture and reused in at least 14 consecutive cycles without measurable loss of activity. Moreover, the catalytic acylation reaction could be performed under neat and continuous-flow conditions for at least 536h of continuous work with the same catalyst activity. [PUBLICATION ABSTRACT] We report herein for the first time the incorporation of a versatile organocatalyst, 4‐(N,N‐dimethylamino)pyridine (DMAP), into the network of a nanoporous conjugated polymer (NCP) by the “bottom‐up” approach. The resulting DMAP‐NCP material possesses highly concentrated and homogeneously distributed DMAP catalytic sites (2.02 mmol g−1). DMAP‐NCP also exhibits enhanced stability and permanent porosity due to the strong covalent linkage and the rigidity of the “bottom‐up” monomers. As a result, DMAP‐NCP shows excellent catalytic activity in the acylation of alcohols with yields of 92–99 %. The DMAP‐NCP catalyst could be easily recovered from the reaction mixture and reused in at least 14 consecutive cycles without measurable loss of activity. Moreover, the catalytic acylation reaction could be performed under neat and continuous‐flow conditions for at least 536 h of continuous work with the same catalyst activity. Nanoporous catalyst: DMAP‐NCP, a new network nanoporous conjugated polymer containing 4‐(N,N‐dimethylamino)pyridine catalytic moieties, has been constructed by the “bottom‐up” strategy. It shows excellent activity and recyclability in the acylation of alcohols and phenols, even under neat and continuous‐flow conditions (see figure). This study demonstrates the possibility of using DMAP‐NCP as a robust and effective heterogeneous catalyst, especially for practical applications on a large scale. We report herein for the first time the incorporation of a versatile organocatalyst, 4-(N,N-dimethylamino)pyridine (DMAP), into the network of a nanoporous conjugated polymer (NCP) by the "bottom-up" approach. The resulting DMAP-NCP material possesses highly concentrated and homogeneously distributed DMAP catalytic sites (2.02 mmol g(-1)). DMAP-NCP also exhibits enhanced stability and permanent porosity due to the strong covalent linkage and the rigidity of the "bottom-up" monomers. As a result, DMAP-NCP shows excellent catalytic activity in the acylation of alcohols with yields of 92-99 %. The DMAP-NCP catalyst could be easily recovered from the reaction mixture and reused in at least 14 consecutive cycles without measurable loss of activity. Moreover, the catalytic acylation reaction could be performed under neat and continuous-flow conditions for at least 536 h of continuous work with the same catalyst activity. We report herein for the first time the incorporation of a versatile organocatalyst, 4-(N,N-dimethylamino)pyridine (DMAP), into the network of a nanoporous conjugated polymer (NCP) by the "bottom-up" approach. The resulting DMAP-NCP material possesses highly concentrated and homogeneously distributed DMAP catalytic sites (2.02 mmol g(-1)). DMAP-NCP also exhibits enhanced stability and permanent porosity due to the strong covalent linkage and the rigidity of the "bottom-up" monomers. As a result, DMAP-NCP shows excellent catalytic activity in the acylation of alcohols with yields of 92-99 %. The DMAP-NCP catalyst could be easily recovered from the reaction mixture and reused in at least 14 consecutive cycles without measurable loss of activity. Moreover, the catalytic acylation reaction could be performed under neat and continuous-flow conditions for at least 536 h of continuous work with the same catalyst activity.We report herein for the first time the incorporation of a versatile organocatalyst, 4-(N,N-dimethylamino)pyridine (DMAP), into the network of a nanoporous conjugated polymer (NCP) by the "bottom-up" approach. The resulting DMAP-NCP material possesses highly concentrated and homogeneously distributed DMAP catalytic sites (2.02 mmol g(-1)). DMAP-NCP also exhibits enhanced stability and permanent porosity due to the strong covalent linkage and the rigidity of the "bottom-up" monomers. As a result, DMAP-NCP shows excellent catalytic activity in the acylation of alcohols with yields of 92-99 %. The DMAP-NCP catalyst could be easily recovered from the reaction mixture and reused in at least 14 consecutive cycles without measurable loss of activity. Moreover, the catalytic acylation reaction could be performed under neat and continuous-flow conditions for at least 536 h of continuous work with the same catalyst activity. We report herein for the first time the incorporation of a versatile organocatalyst, 4‐( N,N ‐dimethylamino)pyridine (DMAP), into the network of a nanoporous conjugated polymer (NCP) by the “bottom‐up” approach. The resulting DMAP‐NCP material possesses highly concentrated and homogeneously distributed DMAP catalytic sites (2.02 mmol g −1 ). DMAP‐NCP also exhibits enhanced stability and permanent porosity due to the strong covalent linkage and the rigidity of the “bottom‐up” monomers. As a result, DMAP‐NCP shows excellent catalytic activity in the acylation of alcohols with yields of 92–99 %. The DMAP‐NCP catalyst could be easily recovered from the reaction mixture and reused in at least 14 consecutive cycles without measurable loss of activity. Moreover, the catalytic acylation reaction could be performed under neat and continuous‐flow conditions for at least 536 h of continuous work with the same catalyst activity. |
| Author | Du, Xin Wang, Wei David Wang, Wei Shi, Jiao Yi Sun, Ya Lei Zhang, Yuan Zhang, Yong |
| Author_xml | – sequence: 1 givenname: Yuan surname: Zhang fullname: Zhang, Yuan organization: State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou, Gansu 730000 (P.R. China), Fax: (+86) 931-8915557 – sequence: 2 givenname: Yong surname: Zhang fullname: Zhang, Yong organization: State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou, Gansu 730000 (P.R. China), Fax: (+86) 931-8915557 – sequence: 3 givenname: Ya Lei surname: Sun fullname: Sun, Ya Lei organization: State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou, Gansu 730000 (P.R. China), Fax: (+86) 931-8915557 – sequence: 4 givenname: Xin surname: Du fullname: Du, Xin organization: State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou, Gansu 730000 (P.R. China), Fax: (+86) 931-8915557 – sequence: 5 givenname: Jiao Yi surname: Shi fullname: Shi, Jiao Yi organization: State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou, Gansu 730000 (P.R. China), Fax: (+86) 931-8915557 – sequence: 6 givenname: Wei David surname: Wang fullname: Wang, Wei David organization: State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou, Gansu 730000 (P.R. China), Fax: (+86) 931-8915557 – sequence: 7 givenname: Wei surname: Wang fullname: Wang, Wei email: wang_wei@lzu.edu.cn organization: State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou, Gansu 730000 (P.R. China), Fax: (+86) 931-8915557 |
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| SSID | ssj0009633 |
| Score | 2.3335304 |
| Snippet | We report herein for the first time the incorporation of a versatile organocatalyst, 4‐(N,N‐dimethylamino)pyridine (DMAP), into the network of a nanoporous... We report herein for the first time the incorporation of a versatile organocatalyst, 4‐( N,N ‐dimethylamino)pyridine (DMAP), into the network of a nanoporous... We report herein for the first time the incorporation of a versatile organocatalyst, 4-(N,N-dimethylamino)pyridine (DMAP), into the network of a nanoporous... |
| SourceID | proquest pubmed crossref wiley istex |
| SourceType | Aggregation Database Index Database Enrichment Source Publisher |
| StartPage | 6328 |
| SubjectTerms | 4-Aminopyridine - analogs & derivatives 4-Aminopyridine - chemical synthesis 4-Aminopyridine - chemistry acylation Catalysis Chemistry heterogeneous catalysis Molecular Structure nanoporous structures Nanostructures - chemistry organocatalysis Polymers Polymers - chemistry Porosity Proteins Rigidity |
| Title | 4-(N,N-Dimethylamino)pyridine-Embedded Nanoporous Conjugated Polymer as a Highly Active Heterogeneous Organocatalyst |
| URI | https://api.istex.fr/ark:/67375/WNG-N1Z22RJ3-H/fulltext.pdf https://onlinelibrary.wiley.com/doi/abs/10.1002%2Fchem.201103028 https://www.ncbi.nlm.nih.gov/pubmed/22467297 https://www.proquest.com/docview/1223798445 https://www.proquest.com/docview/1011179334 |
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