5-Hydroxymethylfurfural-Derived Boron-DipyrrometheneImmobilized on Resin Support as a Sustainable Catalyst for C–HArylation of Heterocycles

摘要

5-Hydroxymethylfurfural (HMF) was used as a sustainable raw material in the development of a resin-supported boron-dipyrromethene (BODIPY)-based photocatalyst. In the development of the catalyst, the brominated product (HMF-BODIPY-Br) and photocatalyst (HMF-BODIPY-Br-Suc) were isolated under a chromatography-free condition. The photocatalyst was loaded on polymeric resin by bridging alcohol functionality in HMF and amine functionality in polymeric resin using succinic anhydride. The resin-supported photocatalyst was used in light-mediated C–H arylation of various heterocycles using aryldiazonium salt. For representative examples, diazotization and photoarylation were carried out in one pot, and arylated furans were obtained in very good yields. C–H arylation was found to proceed via a photogenerated radical intermediate, and the radical intermediate was trapped by forming an adduct with TEMPO.