Defluorination of fluorophenols by a nonheme iron(IV)‐oxo species: observation of a new intermediate along the reaction

Umesh Kumar Bagha, Rolly Yadav, Thirakorn Mokkawes, Jagnyesh Kumar Satpathy, Devesh Kumar, Chivukula V. Sastri, Samuel P. De visser

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High-valent iron(IV)-oxo intermediates are versatile oxidants in the biotransformation of various substrates by metalloenzymes and catalyze essential reactions for human health but also in the biodegradation of toxic organic pollutants in the environment. Herein, we report a biomimetic system that efficiently reacts with fluorophenols through defluorination reactions and trap and characterize various short-lived intermediates along the reaction mechanism. We present the synthesis and characterization of a nonheme iron(IV)-oxo species and study its reactivity patterns with a series of trihalophenols (X = F, Cl, Br). A combined experimental and computational study reveals that the oxidative dehalogenation of 2,4,6-trifluorophenol is initiated with an H-atom abstraction from the phenolic group by the iron(IV)-oxo species resulting in the formation of a phenolate radical and an iron(III)-hydroxo species. This iron(III)-hydroxo species forms an adduct with the oxidized substrate with lmax at 558 nm which subsequently decays to give quinones as products.
Original languageEnglish
JournalChemistry – A European Journal
Early online date17 Apr 2023
Publication statusE-pub ahead of print - 17 Apr 2023


  • inorganic reaction mechanism
  • biomimetic models
  • kinetics
  • defluorination
  • density functional theory

Research Beacons, Institutes and Platforms

  • Manchester Institute of Biotechnology


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