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Issue 23, 2016
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Searching for novel reusable biomass-derived solvents: furfuryl alcohol/water azeotrope as a medium for waste-minimised copper-catalysed azide–alkyne cycloaddition

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Abstract

Herein, we report the first application of the furfuryl alcohol/water azeotrope as a sustainable and easily recoverable reaction medium in organic chemistry. The applicability of this novel medium was tested in copper-catalysed azide–alkyne cycloaddition (CuAAC), a reaction usually conducted in mixtures of water and an organic solvent. Our reaction conditions allowed the isolation of the expected triazoles in generally good yields and usually in shorter times compared to classical reaction conditions, also proving a wide substrate scope. A large fraction of the furfuryl alcohol/water azeotrope can be recovered by simple distillation at the end of the reaction, which results in a dramatic decrease in waste production and E-factors, compared to typically employed CuAAC procedures.

Graphical abstract: Searching for novel reusable biomass-derived solvents: furfuryl alcohol/water azeotrope as a medium for waste-minimised copper-catalysed azide–alkyne cycloaddition

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Supplementary files

Article information


Submitted
16 Jul 2016
Accepted
12 Sep 2016
First published
12 Sep 2016

Green Chem., 2016,18, 6380-6386
Article type
Paper

Searching for novel reusable biomass-derived solvents: furfuryl alcohol/water azeotrope as a medium for waste-minimised copper-catalysed azide–alkyne cycloaddition

D. Rasina, A. Lombi, S. Santoro, F. Ferlin and L. Vaccaro, Green Chem., 2016, 18, 6380
DOI: 10.1039/C6GC01941B

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