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氨基聚苯乙烯负载的六甘醇桥连离子液体作为水介导亲核羟基化反应的高效非均相催化剂。

Amino-polystyrene supported hexaethylene glycol-bridged ionic liquid as an efficient heterogeneous catalyst for water-mediated nucleophilic hydroxylation.

作者信息

Reddy Mudumala Veeranarayana, Kang Seok Min, Yoo Suah, Woo Sang Sik, Kim Dong Wook

机构信息

Department of Chemistry and Chemical Engineering, World Class Smart Laboratory (WCSL), Inha University 100 Inha-ro, Nam-gu Incheon 402-751 Korea

出版信息

RSC Adv. 2019 Mar 25;9(17):9435-9442. doi: 10.1039/c9ra00590k. eCollection 2019 Mar 22.

DOI:10.1039/c9ra00590k
PMID:35520729
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9062187/
Abstract

We report a simple and eco-friendly method for producing an amino-polystyrene supported hexaethylene glycol-bridged ionic liquid (APS-HEGBIL) based on the copolymerization of amino-styrene with 1-vinyl imidazolium ionic liquid bearing hexaethylene glycol moieties, and its characterization by several analytical techniques. The resulting APS-HEGBIL catalyst was found to be remarkably efficient at catalyzing the selective nucleophilic hydroxylation of alkyl halides to produce the corresponding alcohols in water, which acted as a solvent and a nucleophilic hydroxide source. The catalyst was easily recycled and maintained its catalytic activity and stability after ten cycles with excellent yields. The main attributes of the catalyst were that it significantly enhanced the nucleophilicity of water during reactions and promoted the rapid conversions of polar and base-sensitive alkyl halide reactants to alcohols in excellent yields. The combination of ionic liquids and polymeric materials afforded quasi-homogeneous catalysts that were recycled by simple filtration and provided environmentally benign means for conducted catalytic procedures.

摘要

我们报道了一种基于氨基苯乙烯与带有六甘醇部分的1-乙烯基咪唑鎓离子液体的共聚反应制备氨基聚苯乙烯负载的六甘醇桥联离子液体(APS-HEGBIL)的简单且环保的方法,以及通过多种分析技术对其进行的表征。结果发现,所得的APS-HEGBIL催化剂在催化卤代烃在水中选择性亲核羟基化以生成相应醇类方面具有显著的效率,水在反应中既是溶剂又是亲核氢氧化物源。该催化剂易于回收,经过十次循环后仍保持其催化活性和稳定性,产率优异。该催化剂的主要特性在于,它在反应过程中显著增强了水的亲核性,并以优异的产率促进了极性和对碱敏感的卤代烃反应物快速转化为醇类。离子液体和聚合物材料的结合提供了准均相催化剂,这些催化剂通过简单过滤即可回收,并为进行催化过程提供了环境友好的方法。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8160/9062187/9cf3b3d54c66/c9ra00590k-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8160/9062187/f9bb10de9bed/c9ra00590k-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8160/9062187/1b325b52cf37/c9ra00590k-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8160/9062187/bab336647ba0/c9ra00590k-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8160/9062187/d9de6558bb0e/c9ra00590k-f3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8160/9062187/8bc5c3b66dfa/c9ra00590k-f4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8160/9062187/9cf3b3d54c66/c9ra00590k-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8160/9062187/f9bb10de9bed/c9ra00590k-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8160/9062187/1b325b52cf37/c9ra00590k-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8160/9062187/bab336647ba0/c9ra00590k-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8160/9062187/d9de6558bb0e/c9ra00590k-f3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8160/9062187/8bc5c3b66dfa/c9ra00590k-f4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8160/9062187/9cf3b3d54c66/c9ra00590k-s2.jpg

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