Superelectrophilic activation of 5-hydroxymethylfurfural and 2,5-diformylfuran: organic synthesis based on biomass-derived products
| Autor: | T. O. Artamonova, Aleksander V. Vasilyev, Anton A.Tarakanov, Irina A. Boyarskaya, Mikhail O. Kompanets, Dmitry S. Ryabukhin, Dmitry N. Zakusilo, Iosyp O. Opeida, Mikhail A. Khohodorkovskiy |
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| Rok vydání: | 2016 |
| Předmět: |
Biomass
Protonation zeolites 010402 general chemistry 01 natural sciences Full Research Paper lcsh:QD241-441 chemistry.chemical_compound Nucleophile lcsh:Organic chemistry Organic chemistry lcsh:Science Friedel–Crafts reaction 5-hydroxymethylfurfural superacids 010405 organic chemistry Organic Chemistry Nuclear magnetic resonance spectroscopy 0104 chemical sciences Solvent Chemistry chemistry Organic synthesis lcsh:Q Triflic acid 2 5-diformylfuran |
| Zdroj: | Beilstein Journal of Organic Chemistry Beilstein Journal of Organic Chemistry, Vol 12, Iss 1, Pp 2125-2135 (2016) |
| ISSN: | 1860-5397 |
| Popis: | 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 of 17–91%) and 2-arylmethyl-5-(diarylmethyl)furans (yields of 10–37%). The formation of these two types of reaction products depends on the nucleophilicity of the arene. The same reactions under the action of acidic zeolites H-USY in high 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. |
| Databáze: | OpenAIRE |
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