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Synthesis and characterization of a novel oxo-bridged binuclear iron(III) complex: its catalytic application in the synthesis of benzoxazoles using benzyl alcohol in water

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Abstract

In the present work, the synthesis and characterization of a novel binuclear oxo-bridged iron(III) complex, (FeLAPIP)2O, where LAPIP is the deprotonated form of a tetradentateo-aminophenol-iminopyridine ligand, is described. The iron complex was characterized using different techniques including X-ray crystallography, infrared spectroscopy, UV-Vis, magnetic susceptibility and cyclic voltammetry. The X-ray structure analysis revealed that in the structure of the (FeLAPIP)2O complex, each iron(III) is coordinated in a distorted square pyramidal arrangement by an oxo group, three amine nitrogens and one oxygen atom of the o-aminophenolate ligand. The variable-temperature magnetic measurement exhibits strong antiferromagnetic coupling between two iron(III) centers. Cyclic voltammetry measurements showed two kinds of quasireversible events, suggesting the formation of a phenoxyl radical species in the region of the anodic peaks and a metal-centered redox (FeIII/FeII) process at low potential. The catalytic activity of this Fe-complex was evaluated in coupling of 2-aminophenol and benzyl alcohols for the one-pot synthesis of benzoxazoles. The catalyst system showed high catalytic activity in this transformation and benzoxazole derivatives were obtained in good to excellent yields. tert-Butyl hydroperoxide was used as an oxidant and 1.2 mol% of catalyst was needed to accomplish the reaction in water as the green solvent.

Graphical abstract: Synthesis and characterization of a novel oxo-bridged binuclear iron(iii) complex: its catalytic application in the synthesis of benzoxazoles using benzyl alcohol in water

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Publication details

The article was received on 23 Feb 2018, accepted on 04 Apr 2018 and first published on 04 Apr 2018


Article type: Paper
DOI: 10.1039/C8NJ00921J
Citation: New J. Chem., 2018, Advance Article
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    Synthesis and characterization of a novel oxo-bridged binuclear iron(III) complex: its catalytic application in the synthesis of benzoxazoles using benzyl alcohol in water

    E. Safaei, Z. Alaji, F. Panahi, A. Wojtczak and J. Z. Jagličić, New J. Chem., 2018, Advance Article , DOI: 10.1039/C8NJ00921J

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