Pd‐Catalyzed Activation of Carbon–Carbon Bonds in Hydroxymethylfurfural Derivatives

Abstract

AbstractPalladium‐catalyzed activation of C−C bonds in organic molecules is a powerful tool for the synthesis of value‐added compounds. 5‐Hydroxymethylfurfural (HMF) derivatives are a promising class of biomass‐derived chemicals that have received considerable attention due to their potential applications in the synthesis of biologically active molecules and materials. However, the selective activation of unstrained C−C bonds is a challenging task, mainly due to their relatively high bond dissociation energies. Herein, we report a palladium‐catalyzed method for the efficient C−C bond activation of HMF derivatives, enabling their arylation with iodobenzenes. Mechanistic studies, including reaction‐profile analysis, competition experiments and head‐space IR spectroscopy suggest a decarboxylative mechanism.