Near quantitative conversion of xylose into bisfuran. Issue 13 (15th June 2022)

• Record Type: Journal Article
• Authors: Zhang, Rui; Eronen, Aleksi; Vasko, Petra; Du, Xiangze; Install, Joseph; Repo, Timo
• Is Part Of: Green chemistry. Volume 24:Issue 13(2022)
• Page Start: 5052
• Page End: 5057
• Publication Date: 2022-06-15
• Subjects: Environmental chemistry -- Industrial applications -- Periodicals; Environmental management -- Periodicals; 660
• DOI: 10.1039/d2gc00640e
• Languages: English
• ISSNs: 1463-9262

Abstract

Abstract : Xylose is converted to a new type of bisfuranic compound in nearly quantitative yield with acetylacetone, through a Zr-catalysed Garcia Gonzalez reaction-based strategy by losing five molecules of water. 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.