Superelectrophilic Activation of 5-hydroxymethylfurfural and 2,5-diformylfuran: Organic Synthesis Based on Biomass-derived Products

Overview

Journal Beilstein J Org Chem

Specialty Chemistry

Date 2016 Nov 11

PMID 27829919

Citations 5

Authors

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

Affiliations

Soon will be listed here.

Abstract

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 AlBr 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.

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