The Use of 5-Hydroxymethylfurfural towards Fine Chemicals: Synthesis and Direct Arylation of 5-HMF-Based Oxazoles - Archive ouverte HAL Accéder directement au contenu
Article Dans Une Revue SYNLETT Année : 2021

The Use of 5-Hydroxymethylfurfural towards Fine Chemicals: Synthesis and Direct Arylation of 5-HMF-Based Oxazoles

Résumé

Abstract :5-Hydroxymethylfurfural (5-HMF) is a renewable platform chemical used as a source for obtaining diverse fine chemicals. In this letter, we report the synthesis of 5-HMF-based oxazole compounds. While 5-HMF could be easily converted into the oxazole derivative through the Van Leusen reaction, the direct arylation step needed to access the final compounds was problematic at first. After optimization, a palladium-catalyzed procedure has been developed and used for the synthesis of a series of 33 derivatives. This article reports an extension of the late-stage CH arylation reaction as an application to the oxazole platform derived from biosourced 5-HMF. The challenges in the preparation of the derivatives containing some electron-withdrawing substituents were overcome by the use of a palladium-free method.

Domaines

Chimie organique
Fichier non déposé

Dates et versions

hal-03435222 , version 1 (18-11-2021)

Identifiants

Citer

Rafael da Rosa, Lucie Grand, Eloir Schenkel, Lílian Sibelle Campos Bernardes, Maïwenn Jacolot, et al.. The Use of 5-Hydroxymethylfurfural towards Fine Chemicals: Synthesis and Direct Arylation of 5-HMF-Based Oxazoles. SYNLETT, 2021, 32 (08), pp.838-844. ⟨10.1055/a-1335-7330⟩. ⟨hal-03435222⟩
28 Consultations
0 Téléchargements

Altmetric

Partager

Gmail Facebook X LinkedIn More