Oxidation of 2-aminophenol by iron(III) isoindoline complexes

Miklós Szávuly, Róbert Csonka, Gábor Speier, Réka Barabás, Michel Giorgi, József Kaizer

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10 Citations (Scopus)

Abstract

Series of dichloroiron(III) complexes of 1,3-bis(2′-arylimino) isoindoline, including a new structurally characterized ligand 1,3-bis(5′-methyl-2′-thiazolylimino)isoindoline and its complex, have been used as catalysts for the oxidative coupling of 2-aminophenol (OAPH) to 2-aminophenoxazine-3-one (APX) in DMF solution at ambient temperature. The complexes were suitable as catalyst, and depending on the oxidant used, two different mechanisms can be proposed, namely a metal-based oxidation for dioxygen, and a hydroxyl radical mediated process, including zero-order dependence on the concentration of the substrate, for H2O 2. In the former case a mechanism on the basis of kinetic data was proposed assuming ternary complex formation between catalyst, substrate and dioxygen, and a nice correlation was found between the reaction rate and the oxidation potential, E° ′pa of the iron center in the precursor complexes.

Original languageEnglish
Pages (from-to)120-126
Number of pages7
JournalJournal of Molecular Catalysis A: Chemical
Volume392
DOIs
Publication statusPublished - Oct 2014

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Keywords

  • 2-Aminophenol
  • 2-Aminophenoxazine-3-one
  • Biomimetic oxidation
  • Iron(III)
  • Kinetics

ASJC Scopus subject areas

  • Catalysis
  • Process Chemistry and Technology
  • Physical and Theoretical Chemistry

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