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The Suzuki-Miyaura reaction as a tool for modification of phenoxyl-nitroxyl radicals of the 4 : H -imidazole N -oxide series. / Ten, Yury A.; Salnikov, Oleg G.; Amitina, Svetlana A. et al.

In: RSC Advances, Vol. 8, No. 46, 01.01.2018, p. 26099-26107.

Research output: Contribution to journal › Article › peer-review

Harvard

Ten, YA, Salnikov, OG, Amitina, SA, Stass, DV, Rybalova, TV, Kazantsev, MS, Bogomyakov, AS, Mostovich, EA & Mazhukin, DG 2018, 'The Suzuki-Miyaura reaction as a tool for modification of phenoxyl-nitroxyl radicals of the 4: H -imidazole N -oxide series', RSC Advances, vol. 8, no. 46, pp. 26099-26107. https://doi.org/10.1039/c8ra05103h

APA

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. (2018). The Suzuki-Miyaura reaction as a tool for modification of phenoxyl-nitroxyl radicals of the 4: H -imidazole N -oxide series. RSC Advances, 8(46), 26099-26107. https://doi.org/10.1039/c8ra05103h

Vancouver

Ten YA, Salnikov OG, Amitina SA, Stass DV, Rybalova TV, Kazantsev MS et al. The Suzuki-Miyaura reaction as a tool for modification of phenoxyl-nitroxyl radicals of the 4: H -imidazole N -oxide series. RSC Advances. 2018 Jan 1;8(46):26099-26107. doi: 10.1039/c8ra05103h

Author

Ten, Yury A. ; Salnikov, Oleg G. ; Amitina, Svetlana A. et al. / The Suzuki-Miyaura reaction as a tool for modification of phenoxyl-nitroxyl radicals of the 4 : H -imidazole N -oxide series. In: RSC Advances. 2018 ; Vol. 8, No. 46. pp. 26099-26107.

BibTeX

@article{2965fac216964bb8bf5c3c8cbee16d84,
title = "The Suzuki-Miyaura reaction as a tool for modification of phenoxyl-nitroxyl radicals of the 4: H -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.",
author = "Ten, {Yury A.} and Salnikov, {Oleg G.} and Amitina, {Svetlana A.} and Stass, {Dmitri V.} and Rybalova, {Tatyana V.} and Kazantsev, {Maxim S.} and Bogomyakov, {Artem S.} and Mostovich, {Evgeny A.} and Mazhukin, {Dmitrii G.}",
note = "This journal is {\textcopyright} The Royal Society of Chemistry.",
year = "2018",
month = jan,
day = "1",
doi = "10.1039/c8ra05103h",
language = "English",
volume = "8",
pages = "26099--26107",
journal = "RSC Advances",
issn = "2046-2069",
publisher = "ROYAL SOC CHEMISTRY",
number = "46",

}

RIS

TY - JOUR

T1 - The Suzuki-Miyaura reaction as a tool for modification of phenoxyl-nitroxyl radicals of the 4

T2 - H -imidazole N -oxide series

AU - Ten, Yury A.

AU - Salnikov, Oleg G.

AU - Amitina, Svetlana A.

AU - Stass, Dmitri V.

AU - Rybalova, Tatyana V.

AU - Kazantsev, Maxim S.

AU - Bogomyakov, Artem S.

AU - Mostovich, Evgeny A.

AU - Mazhukin, Dmitrii G.

N1 - This journal is © The Royal Society of Chemistry.

PY - 2018/1/1

Y1 - 2018/1/1

N2 - 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.

AB - 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.

UR - http://www.scopus.com/inward/record.url?scp=85050608086&partnerID=8YFLogxK

U2 - 10.1039/c8ra05103h

DO - 10.1039/c8ra05103h

M3 - Article

C2 - 35541934

AN - SCOPUS:85050608086

VL - 8

SP - 26099

EP - 26107

JO - RSC Advances

JF - RSC Advances

SN - 2046-2069

IS - 46

ER -

ID: 15962086