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

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.

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  • 1State Key Laboratory and Institute of Elemento-Organic Chemistry, Nankai University, Tianjin, PR China.

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.

PMID:
18473439
[PubMed]
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