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Issue 10, 2010
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Lewis basic ionic liquids-catalyzed synthesis of 5-aryl-2-oxazolidinones from aziridines and CO2 under solvent-free conditions

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Abstract

A series of easily prepared Lewis basic ionic liquids were developed as recyclable and efficient catalysts for selective synthesis of 5-aryl-2-oxazolidinones from aziridines and CO2 without utilization of any organic solvent or additive. Notably, high conversion, chemo- and regio-selectivity were attained when 1-butyl-4-aza-1-azaniabicyclo[2.2.2]octane bromide ([C4DABCO]Br) was used as the catalyst. Furthermore, the catalyst could be recycled over four times without appreciable loss of catalytic activity. The effects of the catalyst structure and various reaction parameters on the catalytic performance were investigated in detail. This protocol was found to be applicable to a variety of aziridines producing the corresponding 5-aryl-2-oxazolidinones in good yields and excellent regioselectivities. Therefore, this solvent-free process thus represents an environmentally friendly process for ionic liquid-catalyzed conversion of CO2 into value-added chemicals. A possible catalytic cycle for CO2 activation induced by nucleophilic tertiary nitrogen of the ionic liquid was proposed, based on studies using in situ FT-IR spectroscopy under CO2 pressure.

Graphical abstract: Lewis basic ionic liquids-catalyzed synthesis of 5-aryl-2-oxazolidinones from aziridines and CO2 under solvent-free conditions

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Publication details

The article was received on 04 Jul 2010, accepted on 02 Aug 2010 and first published on 06 Sep 2010


Article type: Paper
DOI: 10.1039/C0GC00286K
Green Chem., 2010,12, 1850-1854

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    Lewis basic ionic liquids-catalyzed synthesis of 5-aryl-2-oxazolidinones from aziridines and CO2 under solvent-free conditions

    Z. Yang, L. He, S. Peng and A. Liu, Green Chem., 2010, 12, 1850
    DOI: 10.1039/C0GC00286K

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