Issue 46, 2018, Issue in Progress

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

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

Supplementary files

Article information

Article type
Paper
Submitted
13 Jun 2018
Accepted
13 Jul 2018
First published
20 Jul 2018
This article is Open Access
Creative Commons BY-NC license

RSC Adv., 2018,8, 26099-26107

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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