Continuous N-alkylation reactions of amino alcohols using γ-Al2O3 and supercritical CO2: unexpected formation of cyclic ureas and urethanes by reaction with CO2

Streng, Emelia S. and Lee, Darren S. and George, Michael W. and Poliakoff, Martyn (2017) Continuous N-alkylation reactions of amino alcohols using γ-Al2O3 and supercritical CO2: unexpected formation of cyclic ureas and urethanes by reaction with CO2. Beilstein Journal of Organic Chemistry, 13 . pp. 329-337. ISSN 1860-5397

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Abstract

The use of γ-Al2O3 as a heterogeneous catalyst in scCO2, has be successfully applied to the amination of alcohols for the synthesis of N-alkylated heterocycles. The optimal reaction conditions (temperature and substrate flow rate) were determined using an automated self-optimising reactor, resulting in moderate to high yields of the target products. Carrying out the reaction in scCO2 was shown to be beneficial, as higher yields were obtained in the presence of CO2 than in its absence. A surprising discovery is that, in addition to cyclic amines, cyclic ureas and urethanes could be synthesised by incorporation of CO2 from the supercritical solvent into the product.

Item Type: Article
Keywords: Continuous flow; heterocycle; N-alkylation; self-optimisation; supercritical CO2
Schools/Departments: University of Nottingham, UK > Faculty of Science > School of Chemistry
Identification Number: 10.3762/bjoc.13.36
Depositing User: Bramwell, Roseanna
Date Deposited: 09 Mar 2017 13:56
Last Modified: 09 Mar 2017 14:02
URI: http://eprints.nottingham.ac.uk/id/eprint/41185

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