Solvent issues in the Baylis-Hillman reaction of 5-hydroxymethyl furfural (HMF) and 5-glucosyloxymethyl furfural (GMF). Towards no-solvent conditions

Lianjie Wang (1) , Jia-Neng Tan (1) , Mohammed Ahmar (1) , Yves Queneau (1)

1 COB - Chimie Organique et Bioorganique

The possibility to apply solventless conditions for the Baylis-Hillman reaction of 5-hydroxymethyl furfural (HMF) and its glucosylated analogue, glucosyloxymethyl furfural (GMF) has been investigated. This study shows that highly functionalized adducts can be obtained in fair to good yields, under the conditions combining the renewability of the substrates, the straightforwardness of the strategy, and the lowered cost and toxicity of the solvent conditions. The issue of the polarity of the furanic substrate is addressed by comparing HMF with furfural and GMF.

Keywords: GMF; HMF; Morita-Baylis-Hillman reaction; no-solvent; carbohydrate

Domains: Chemical Sciences; Organic chemistry

Lianjie Wang, Jia-Neng Tan, Mohammed Ahmar, Yves Queneau. Solvent issues in the Baylis-Hillman reaction of 5-hydroxymethyl furfural (HMF) and 5-glucosyloxymethyl furfural (GMF). Towards no-solvent conditions. Pure and Applied Chemistry, 2019, 91 (7), pp.1149-1158. ⟨10.1515/pac-2019-0215⟩. ⟨hal-02193113⟩