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

2-(3,5-Di- -butyl-4-hydroxyphenyl)-5-(4-iodophenyl)-4,4-dimethyl-4 -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 4 -imidazole- -oxide. Interaction of the same compound with B...

Full description

Saved in:
Bibliographic Details
Published in:RSC advances 2018, Vol.8 (46), p.26099-26107
Main Authors: Ten, Yury A, Salnikov, Oleg G, Amitina, Svetlana A, Stass, Dmitri V, Rybalova, Tatyana V, Kazantsev, Maxim S, Bogomyakov, Artem S, Mostovich, Evgeny A, Mazhukin, Dmitrii G
Format: Article
Language:English
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:2-(3,5-Di- -butyl-4-hydroxyphenyl)-5-(4-iodophenyl)-4,4-dimethyl-4 -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 4 -imidazole- -oxide. Interaction of the same compound with B (pin) in the presence of PdCl (PPh ) 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- -butyl-4-[1-oxido-4-(biphenyl-4-yl)-5,5-dimethyl-1 -imidazole-2(5 )-ylidene]cyclohex-2,5-dienone, its magnetic susceptibility, EPR spectra of the obtained hybrid radicals in solution, and cyclic voltammetry characteristics of 4 -imidazoles were studied.
ISSN:2046-2069
2046-2069
DOI:10.1039/c8ra05103h