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Issue 16, 2017
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Versatile CO-assisted direct reductive amination of 5-hydroxymethylfurfural catalyzed by a supported gold catalyst

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Abstract

Reductive amination (RA) constitutes an attractive and practical strategy for discovering protocols capable of converting biomass into valuable N-containing compounds. Described herein is a versatile and sustainable RA of 5-hydroxymethyl-furfural (HMF), an important biomass-derived aldehyde, using abundant and cheaply available CO and water as reductants. A single phase rutile titania supported gold (Au/TiO2-R) catalyst is shown to efficiently catalyze this CO/H2O-mediated RA under mild and convenient conditions. With this system, a broad spectrum of primary and secondary amines can be used as suitable substrates and the desired reaction can proceed favourably in a highly chemoselective, efficient and atom-economical fashion. In particular, this protocol can also allow convenient access to bis(hydroxylmethylfurfuryl)-amines, a new group of furan-based monomers with great potential to form functional biopolymers with tunable properties. Moreover, this CO-assisted RA is more efficient (higher TON and TOF) and more eco-friendly (increased resource efficiency) than the previous state-of-the-art technique.

Graphical abstract: Versatile CO-assisted direct reductive amination of 5-hydroxymethylfurfural catalyzed by a supported gold catalyst

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Publication details

The article was received on 29 May 2017, accepted on 05 Jul 2017 and first published on 21 Jul 2017


Article type: Paper
DOI: 10.1039/C7GC01579H
Citation: Green Chem., 2017,19, 3880-3887
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    Versatile CO-assisted direct reductive amination of 5-hydroxymethylfurfural catalyzed by a supported gold catalyst

    M. Zhu, L. Tao, Q. Zhang, J. Dong, Y. Liu, H. He and Y. Cao, Green Chem., 2017, 19, 3880
    DOI: 10.1039/C7GC01579H

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