| Autor: |
Dmitry S. Ryabukhin, Dmitry N. Zakusilo, Mikhail O. Kompanets, Anton A.Tarakanov, Irina A. Boyarskaya, Tatiana O. Artamonova, Mikhail A. Khohodorkovskiy, Iosyp O. Opeida, Aleksander V. Vasilyev |
| Jazyk: |
angličtina |
| Rok vydání: |
2016 |
| Předmět: |
|
| Zdroj: |
Beilstein Journal of Organic Chemistry, Vol 12, Iss 1, Pp 2125-2135 (2016) |
| Druh dokumentu: |
article |
| ISSN: |
1860-5397 |
| DOI: |
10.3762/bjoc.12.202 |
| 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: |
Directory of Open Access Journals |
| Externí odkaz: |
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