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

Autor: Ten YA; NN Vorozhtsov Novosibirsk Institute of Organic Chemistry SB RAS 9 Acad. Lavrentyeva Ave. Novosibirsk 630090 Russia, d-mazhukin@yandex.ru., Salnikov OG; Novosibirsk State University 2 Pirogova Str. Novosibirsk 630090 Russia., Amitina SA; NN Vorozhtsov Novosibirsk Institute of Organic Chemistry SB RAS 9 Acad. Lavrentyeva Ave. Novosibirsk 630090 Russia, d-mazhukin@yandex.ru., Stass DV; Novosibirsk State University 2 Pirogova Str. Novosibirsk 630090 Russia.; Voevodsky Institute of Chemical Kinetics and Combustion SB RAS 3 Institutskaya Str. Novosibirsk 630090 Russia., Rybalova TV; NN Vorozhtsov Novosibirsk Institute of Organic Chemistry SB RAS 9 Acad. Lavrentyeva Ave. Novosibirsk 630090 Russia, d-mazhukin@yandex.ru.; Novosibirsk State University 2 Pirogova Str. Novosibirsk 630090 Russia., Kazantsev MS; NN Vorozhtsov Novosibirsk Institute of Organic Chemistry SB RAS 9 Acad. Lavrentyeva Ave. Novosibirsk 630090 Russia, d-mazhukin@yandex.ru.; Novosibirsk State University 2 Pirogova Str. Novosibirsk 630090 Russia., Bogomyakov AS; International Tomography Center SB RAS 3A Institutskaya Str. Novosibirsk 630090 Russia., Mostovich EA; NN Vorozhtsov Novosibirsk Institute of Organic Chemistry SB RAS 9 Acad. Lavrentyeva Ave. Novosibirsk 630090 Russia, d-mazhukin@yandex.ru.; Novosibirsk State University 2 Pirogova Str. Novosibirsk 630090 Russia., Mazhukin DG; NN Vorozhtsov Novosibirsk Institute of Organic Chemistry SB RAS 9 Acad. Lavrentyeva Ave. Novosibirsk 630090 Russia, d-mazhukin@yandex.ru.; Novosibirsk State University 2 Pirogova Str. Novosibirsk 630090 Russia.
Jazyk: angličtina
Zdroj: RSC advances [RSC Adv] 2018 Jul 20; Vol. 8 (46), pp. 26099-26107. Date of Electronic Publication: 2018 Jul 20 (Print Publication: 2018).
DOI: 10.1039/c8ra05103h
Abstrakt: 2-(3,5-Di- tert -butyl-4-hydroxyphenyl)-5-(4-iodophenyl)-4,4-dimethyl-4 H -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 H -imidazole- N -oxide. Interaction of the same compound with B 2 (pin) 2 in the presence of PdCl 2 (PPh 3 ) 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-1 H -imidazole-2(5 H )-ylidene]cyclohex-2,5-dienone, its magnetic susceptibility, EPR spectra of the obtained hybrid radicals in solution, and cyclic voltammetry characteristics of 4 H -imidazoles were studied.
Competing Interests: There are no conflicts of interest to declare.
(This journal is © The Royal Society of Chemistry.)
Databáze: MEDLINE
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