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季铵溴功能化聚乙二醇:一种在无溶剂条件下由二氧化碳和氮丙啶选择性合成5-芳基-2-恶唑烷酮的高效可回收催化剂。

Quaternary ammonium bromide functionalized polyethylene glycol: a highly efficient and recyclable catalyst for selective synthesis of 5-aryl-2-oxazolidinones from carbon dioxide and aziridines under solvent-free conditions.

作者信息

Du Ya, Wu Ying, Liu An-Hua, He Liang-Nian

机构信息

State Key Laboratory and Institute of Elemento-Organic Chemistry, Nankai University, Tianjin, PR China.

出版信息

J Org Chem. 2008 Jun 20;73(12):4709-12. doi: 10.1021/jo800269v. Epub 2008 May 13.

Abstract

A quaternary ammonium bromide covalently bound to polyethylene glycol (PEG, MW = 6000), i.e., PEG(6000-)(NBu(3)Br)2, was found to be an efficient and recyclable catalyst for the cycloaddition reaction of aziridines to CO(2) under mild conditions without utilization of additional organic solvents or cocatalysts. As a result, 5-aryl-2-oxazolidinone was obtained in high yield with excellent regioselectivity. The catalyst worked well for a wide variety of 1-alkyl-2-arylaziridines. Besides, the catalyst could be recovered by centrifugation and reused without significant loss of catalytic activity and selectivity.

摘要

一种与聚乙二醇(PEG,分子量 = 6000)共价结合的溴化季铵盐,即PEG(6000-)(NBu(3)Br)2,被发现是一种高效且可回收的催化剂,用于在温和条件下使氮丙啶与CO(2)发生环加成反应,无需使用额外的有机溶剂或助催化剂。结果,以高收率和优异的区域选择性得到了5-芳基-2-恶唑烷酮。该催化剂对多种1-烷基-2-芳基氮丙啶都有良好的效果。此外,通过离心可回收该催化剂并重复使用,而催化活性和选择性不会有显著损失。

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