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ChemSusChem. 2017 May 9;10(9):2001-2007. doi: 10.1002/cssc.201700241. Epub 2017 Apr 11.

An Experimental and Theoretical Study on the Unexpected Catalytic Activity of Triethanolamine for the Carboxylative Cyclization of Propargylic Amines with CO2.

Author information

1
Collaborative Innovation Center of Henan Province for Green, Manufacturing of Fine Chemicals, School of Chemistry and Chemical, Engineering, Key Laboratory of Green Chemical Media and Reactions, Ministry of Education, Henan Normal University, Xinxiang, Henan, 453007, P. R. China.
2
Department of Chemical and Petroleum Engineering, University of Wyoming, Laramie, WY, 82071, USA.

Abstract

Chemical conversion of CO2 under atmospheric pressure and metal-free conditions remains a great challenge. In this work, a series of alkanolamines, low-cost and biodegradable bases, were used to catalyze the carboxylative cyclization of propargylic amines with CO2 . Among these alkanolamines, triethanolamine (TEOA) was found to be a highly efficient organocatalyst for this important transformation at atmospheric pressure, and a series of desired products were synthesized in good to excellent yields. After the reactions, TEOA could be easily recovered and reused without obvious reduction in the efficiency. DFT studies revealed that TEOA may activate CO2 to form a ring-shaped carbonate intermediate that plays an important role in the catalysis of the reaction. This finding provides an effective and environmentally friendly alternative route for the production of 2-oxazolidinones.

KEYWORDS:

CO2 conversion; alkanolamines; density functional calculations; heterocycles; organocatalysis

PMID:
28266144
DOI:
10.1002/cssc.201700241
[Indexed for MEDLINE]

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