Issue 19, 2022

Iron-catalysed chemo-selective oxidation of unprotected sugars: application for the competitive oxidation of pentoses from a sugar mixture

Abstract

An iron-catalysed transfer hydrogenation methodology was developed to oxidise aldo-hexoses and -pentoses into sugar lactones using different acceptors. The transformation occurs on unprotected sugars with complete chemo-selectivity for the anomeric position. An application for the competitive oxidation of pentose from a mixture of C5 and C6 sugars is also reported. Finally, we managed to perform the oxidation of xylose with only an equimolar amount of a carefully chosen acceptor, improving drastically the sustainability of the transformation without compromising the equilibrium shift.

Graphical abstract: Iron-catalysed chemo-selective oxidation of unprotected sugars: application for the competitive oxidation of pentoses from a sugar mixture

Supplementary files

Article information

Article type
Paper
Submitted
13 Jul 2022
Accepted
08 Sep 2022
First published
12 Sep 2022

Green Chem., 2022,24, 7682-7688

Iron-catalysed chemo-selective oxidation of unprotected sugars: application for the competitive oxidation of pentoses from a sugar mixture

D. Branquet, M. V. Sidi Boune, N. Hucher, C. Taillier, V. Dalla, S. Comesse and L. Benhamou, Green Chem., 2022, 24, 7682 DOI: 10.1039/D2GC02606F

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