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5‑Hydroxymethylfurfural-Derived Boron-Dipyrromethene Immobilized on Resin Support as a Sustainable Catalyst for C–H Arylation of Heterocycles
journal contribution
posted on 2019-08-23, 13:44 authored by Rajamani Rajmohan, Paulraj Nisha, Pothiappan Vairaprakash5-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.
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Sustainable Catalystresin-supported boron-dipyrrometheneresin-supported photocatalystHeterocycles 5- HydroxymethylfurfuralResin Supportbrominated productamine functionalityaryldiazonium saltarylated furansHMFalcohol functionalityarylationBODIPYchromatography-free conditionsuccinic anhydriderepresentative examples
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