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聚己内酰胺负载的六甘醇咪唑鎓离子液体作为亲核氟化的多相促进剂

Poly Caprolactam Supported Hexaethylene Glycolic Imidazolium Ionic Liquid as a Heterogeneous Promoter for Nucleophilic Fluorination.

作者信息

Reddy Mudumala Veeranarayana, Park Keun Heok, Kim Dong Wook

机构信息

Department of Chemistry and Chemical Engineering, Inha University, 100 Inha-ro, Nam-gu, Incheon 402-751, Republic of Korea.

出版信息

Molecules. 2023 Sep 21;28(18):6747. doi: 10.3390/molecules28186747.

DOI:10.3390/molecules28186747
PMID:37764523
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC10535173/
Abstract

Hexaethylene glycolic vinyl imidazolium (hexaEGVIM) was supported on -vinyl caprolactam via covalent bonds through simple copolymerization to form poly caprolactam-supported hexaethylene glycol-substituted imidazolium salts (PCLS-hexaEGIM). The resulting heterogeneous PCLS-hexaEGIM promoter was active, selective, and stable for aliphatic nucleophilic substitution reactions using alkali metal salts. The alkali metal salts dramatically enhanced the reactivity of this heterogeneous catalyst with easily isolable higher product yields, reducing the formation of by-products. Therefore, nucleophilic fluorination and other substitution reactions can act as highly efficient catalysts in various sulfonyloxyalkanes and haloalkanes with regard to their corresponding fluorinated products.

摘要

通过简单的共聚反应,将六甘醇乙烯基咪唑鎓(hexaEGVIM)通过共价键负载在乙烯基己内酰胺上,形成聚己内酰胺负载的六甘醇取代咪唑鎓盐(PCLS-hexaEGIM)。所得的多相PCLS-hexaEGIM促进剂对于使用碱金属盐的脂肪族亲核取代反应具有活性、选择性和稳定性。碱金属盐显著提高了这种多相催化剂的反应活性,能够轻松分离出更高的产物产率,减少副产物的形成。因此,亲核氟化反应和其他取代反应在各种磺酰氧基烷烃和卤代烷烃生成相应氟化产物的反应中可作为高效催化剂。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5593/10535173/40fe0f36f690/molecules-28-06747-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5593/10535173/ef29c8ffb47c/molecules-28-06747-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5593/10535173/40fe0f36f690/molecules-28-06747-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5593/10535173/ef29c8ffb47c/molecules-28-06747-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5593/10535173/40fe0f36f690/molecules-28-06747-g002.jpg

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本文引用的文献

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Ionic Liquids as Organocatalysts for Nucleophilic Fluorination: Concepts and Perspectives.离子液体作为亲核氟化的有机催化剂:概念与展望。
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Polymer-supported pentaethylene glycol as a facile heterogeneous catalyst for nucleophilic fluorination.聚合物负载五甘醇作为一种简便的非均相氟化反应催化剂。
Org Lett. 2010 Sep 3;12(17):3740-3. doi: 10.1021/ol101485n.
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