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Issue 46, 2018, Issue in Progress
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The Suzuki–Miyaura reaction as a tool for modification of phenoxyl-nitroxyl radicals of the 4H-imidazole N-oxide series

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Abstract

2-(3,5-Di-tert-butyl-4-hydroxyphenyl)-5-(4-iodophenyl)-4,4-dimethyl-4H-imidazole 3-oxide reacts with phenylboronic acid and its substituted derivatives in a cross-coupling reaction of the Suzuki–Miyaura type to form 5-biphenyl derivatives of 4H-imidazole-N-oxide. Interaction of the same compound with B2(pin)2 in the presence of PdCl2(PPh3)2 proceeds through the formation of intermediate 1,3,2-dioxoborolane and leads to the product of homocoupling: biphenyl-bis(imidazole). Oxidation of the resultant imidazoles with lead dioxide quantitatively yields stable conjugated phenoxyl-nitroxyl mono- and diradicals, which are of interest as electroactive paramagnetic materials. The crystal structure of the monoradical, 2,6-di-tert-butyl-4-[1-oxido-4-(biphenyl-4-yl)-5,5-dimethyl-1H-imidazole-2(5H)-ylidene]cyclohex-2,5-dienone, its magnetic susceptibility, EPR spectra of the obtained hybrid radicals in solution, and cyclic voltammetry characteristics of 4H-imidazoles were studied.

Graphical abstract: The Suzuki–Miyaura reaction as a tool for modification of phenoxyl-nitroxyl radicals of the 4H-imidazole N-oxide series

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Publication details

The article was received on 13 Jun 2018, accepted on 13 Jul 2018 and first published on 20 Jul 2018


Article type: Paper
DOI: 10.1039/C8RA05103H
RSC Adv., 2018,8, 26099-26107
  • Open access: Creative Commons BY-NC license
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    The Suzuki–Miyaura reaction as a tool for modification of phenoxyl-nitroxyl radicals of the 4H-imidazole N-oxide series

    Y. A. Ten, O. G. Salnikov, S. A. Amitina, D. V. Stass, T. V. Rybalova, M. S. Kazantsev, A. S. Bogomyakov, E. A. Mostovich and D. G. Mazhukin, RSC Adv., 2018, 8, 26099
    DOI: 10.1039/C8RA05103H

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