Superelectrophilic activation of 5-hydroxymethylfurfural and 2,5-diformylfuran: organic synthesis based on biomass-derived products.

摘要: The reaction of 5-hydroxymethylfurfural (5-HMF) with arenes in superacidic trifluoromethanesulfonic acid (triflic acid, TfOH) as the solvent at room temperature for 1–24 h gives rise to 5-arylmethylfurfurals (yields 17–91%) and 2-arylmethyl-5-(diarylmethyl)furans 10–37%). formation these two types products depends on nucleophilicity arene. same reactions under action acidic zeolites H-USY high pressure tubes 130 °C 1 result only 45–79%). 2,5-Diformylfuran (2,5-DFF) AlBr3 leads 5-(diarylmethyl)furfurals 51–90%). reactive protonated species 5-HMF 2,5-DFF were characterized by NMR spectroscopy TfOH studied DFT calculations. These show possibilities organic synthesis based biomass-derived 2,5-DFF.