Issue 13, 2022

Near quantitative conversion of xylose into bisfuran

Abstract

Renewable and abundant carbohydrates are promising feedstocks for producing valuable chemicals. Here we report a highly efficient Zr-catalysed conversion of xylose and acetylacetone (acac) to a new type of bisfuranic monomer, 1-(4-((4-acetyl-5-methylfuran-2-yl)methyl)-2-methylfuran-3-yl)ethenone (MFE). The formation of MFE stems from the intermediate obtained through the nucleophilic addition of acac to xylose. Under optimized conditions (microwave irradiation, 140 °C, 24 min, NaI as an additive), MFE is obtained in near-quantitative yield (98%). Importantly, the reaction selectivity can be tuned by the inclusion of an additive. When NaCl is used, the reaction gives 3-(furan-2-ylmethylene)pentane-2,4-dione (FMPD, 55%), a jet-fuel precursor, and MFE (30%) with a total carbon yield of 85%. To the best of our knowledge, this is the first report on straightforward xylose transformation to a bisfuranic compound with excellent carbon efficiency. This Garcia Gonzalez (GG) reaction inclusive strategy is remarkable and could lead to many innovations in bio-based polymer synthesis.

Graphical abstract: Near quantitative conversion of xylose into bisfuran

Supplementary files

Article information

Article type
Communication
Submitted
16 fev 2022
Accepted
30 may 2022
First published
31 may 2022
This article is Open Access
Creative Commons BY license

Green Chem., 2022,24, 5052-5057

Near quantitative conversion of xylose into bisfuran

R. Zhang, A. Eronen, P. Vasko, X. Du, J. Install and T. Repo, Green Chem., 2022, 24, 5052 DOI: 10.1039/D2GC00640E

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