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

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

Journal

RSC Advances
ISSN: 2046-2069

Output data

Year: 2018, Volume: 8, Number: 46, Pages: 26099-26107 Pages count : 9 DOI: 10.1039/c8ra05103h

Authors

Ten Yury A. ¹ , Salnikov Oleg G. ² , Amitina Svetlana A. ¹ , Stass Dmitri V. ^2,3 , Rybalova Tatyana V. ^1,2 , Kazantsev Maxim S. ^1,2 , Bogomyakov Artem S. ⁴ , Mostovich Evgeny A. ^1,2 , Mazhukin Dmitrii G. ^1,2

Affiliations

1	(Данные Web of science) NN Vorozhtsov Novosibirsk Inst Organ Chem SB RAS, 9 Acad Lavrentyeva Ave, Novosibirsk 630090, Russia
2	(Данные Web of science) Novosibirsk State Univ, 2 Pirogova Str, Novosibirsk 630090, Russia
3	(Данные Web of science) Voevodsky Inst Chem Kinet & Combust SB RAS, 3 Inst Skaya Str, Novosibirsk 630090, Russia
4	(Данные Web of science) Int Tomog Ctr SB RAS, 3A Inst Skaya Str, Novosibirsk 630090, Russia

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 B-2(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.

Ten Y.A. , Salnikov O.G. , Amitina S.A. , Stass D.V. , Rybalova T.V. , Kazantsev M.S. , Bogomyakov A.S. , Mostovich E.A. , Mazhukin D.G.
The Suzuki-Miyaura reaction as a tool for modification of phenoxyl-nitroxyl radicals of the 4H-imidazole N-oxide series

RSC Advances. 2018. V.8. N46. P.26099-26107. DOI: 10.1039/c8ra05103h WOS Scopus

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