Issue 8, 2019

Utilization of bio-based glycolaldehyde aqueous solution in organic synthesis: application to the synthesis of 2,3-dihydrofurans

Abstract

Glycolaldehyde is a biomass-derived chemical compound available from cellulose or glucose. Until now, little attention has been devoted to its use towards value-added chemicals. To explore novel transformations of glycolaldehyde, in this work, a three-component reaction of glycolaldehyde, indole and a 1,3-dicarbonyl compound was developed to synthesize a class of 3-(indol-3-yl)-2,3-dihydrofurans. Using glycolaldehyde diethyl acetal as a glycolaldehyde source, the reaction can be performed in organic solvents, and two catalytic systems were proved to be effective: (a) Sc(OTf)3/nitromethane and (b) Ni(ClO4)2·6H2O/acetonitrile. However, these conditions applied to the direct use of the bio-based glycolaldehyde aqueous solution did not provide the dihydrofurans efficiently. To enable the use of an aqueous solution of glycolaldehyde, a hitherto unreported deep eutectic solvent (DES) was developed by using FeCl3·6H2O and meglumine (N-methylglucamine) as precursors. The FeCl3·6H2O/meglumine DES was characterized by FTIR, TGA and DSC, and the obtained results demonstrated unambiguously the formation of a DES. This DES was found to be an efficient and water-compatible promoting medium for the abovementioned three-component reaction. A variety of 3-(indol-3-yl)-2,3-dihydrofurans were synthesized in good yields. The FeCl3·6H2O/meglumine DES system can also be recycled without significant loss of activity.

Graphical abstract: Utilization of bio-based glycolaldehyde aqueous solution in organic synthesis: application to the synthesis of 2,3-dihydrofurans

Supplementary files

Article information

Article type
Paper
Submitted
21 Dec 2018
Accepted
05 Mar 2019
First published
06 Mar 2019

Green Chem., 2019,21, 2061-2069

Utilization of bio-based glycolaldehyde aqueous solution in organic synthesis: application to the synthesis of 2,3-dihydrofurans

J. Xu, W. Huang, R. Bai, Y. Queneau, F. Jérôme and Y. Gu, Green Chem., 2019, 21, 2061 DOI: 10.1039/C8GC04000A

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements