Beilstein J. Org. Chem.2018,14, 1436–1445, doi:10.3762/bjoc.14.121
with oxidation of either the alcohol or the aldehyde leading to the dialdehyde 2,5-diformylfuran (DFF) or to 5-hydroxymethyl-2-furancarboxylic acid (HMFCA), respectively (Figure 4a). Subsequent oxidation of DFF and HMFCA leads to 5-formyl-2-furancarboxylic acid (FFCA) and finally to FDCA. The
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Graphical Abstract
Scheme 1:
Conventional water electrolyzer (a) and electrolyzer using an alternative anode reaction (b) in alk...
Beilstein J. Org. Chem.2016,12, 2125–2135, doi:10.3762/bjoc.12.202
pressure tubes at 130 °C for 1 h result in the formation of only 5-arylmethylfurfurals (yields of 45–79%). 2,5-Diformylfuran (2,5-DFF) in the reaction with arenes under the action of AlBr3 at room temperature for 1 h leads to 5-(diarylmethyl)furfurals (yields of 51–90%). The reactive protonated species of
5-HMF and 2,5-DFF were characterized by NMR spectroscopy in TfOH and studied by DFT calculations. These reactions show possibilities of organic synthesis based on biomass-derived 5-HMF and 2,5-DFF.
Keywords: 2,5-diformylfuran; Friedel–Crafts reaction; 5-hydroxymethylfurfural; superacids; zeolites
production of new useful organic substances [26][27][28][29][30].
Based on our recent study on the synthesis of 5-HMF and its oxidation to 2,5-diformylfuran (2,5-DFF) [31] (Figure 1), this work is focused on developing methods of organic synthesis on the basis of electrophilic activation of these biomass
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Graphical Abstract
Figure 1:
Formation of 5-HMF from D-glucose or D-fructose followed by oxidation to 2,5-DFF.