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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.; Lee, Darren S.; George, Michael W.; Poliakoff, Martyn

Authors

Emelia S. Streng

Darren S. Lee

Michael W. George

Martyn Poliakoff



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.

Journal Article Type Article
Publication Date Feb 21, 2017
Journal Beilstein Journal of Organic Chemistry
Print ISSN 1860-5397
Electronic ISSN 1860-5397
Publisher Beilstein-Institut
Peer Reviewed Peer Reviewed
Volume 13
APA6 Citation Streng, E. S., Lee, D. S., George, M. W., & Poliakoff, M. (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, doi:10.3762/bjoc.13.36
DOI https://doi.org/10.3762/bjoc.13.36
Keywords Continuous flow; heterocycle; N-alkylation; self-optimisation; supercritical CO2
Publisher URL http://www.beilstein-journals.org/bjoc/single/articleFullText.htm?publicId=1860-5397-13-36
Copyright Statement Copyright information regarding this work can be found at the following address: http://creativecommons.org/licenses/by/4.0

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Copyright Statement
Copyright information regarding this work can be found at the following address: http://creativecommons.org/licenses/by/4.0





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