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铃木-宫浦反应作为修饰4-咪唑氧化物系列苯氧基-氮氧自由基的一种工具。

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

作者信息

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

机构信息

NN Vorozhtsov Novosibirsk Institute of Organic Chemistry SB RAS 9 Acad. Lavrentyeva Ave. Novosibirsk 630090 Russia,

Novosibirsk State University 2 Pirogova Str. Novosibirsk 630090 Russia.

出版信息

RSC Adv. 2018 Jul 20;8(46):26099-26107. doi: 10.1039/c8ra05103h. eCollection 2018 Jul 19.

DOI:10.1039/c8ra05103h
PMID:35541934
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9082764/
Abstract

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.

摘要

2-(3,5-二叔丁基-4-羟基苯基)-5-(4-碘苯基)-4,4-二甲基-4-咪唑 3-氧化物在铃木-宫浦型交叉偶联反应中与苯基硼酸及其取代衍生物反应，形成 4-咪唑-3-氧化物的 5-联苯衍生物。同一化合物在 PdCl(PPh)存在下与 B(pin)相互作用，通过形成中间体 1,3,2-二氧硼戊环进行反应，并生成均偶联产物：联苯-双(咪唑)。用二氧化铅氧化所得咪唑可定量生成稳定的共轭苯氧基-硝酰基单自由基和双自由基，它们作为电活性顺磁材料具有重要意义。研究了单自由基 2,6-二叔丁基-4-[1-氧化-4-(联苯-4-基)-5,5-二甲基-1-咪唑-2(5)-亚基]环己-2,5-二烯酮的晶体结构、其磁化率、所得混合自由基在溶液中的电子顺磁共振谱以及 4-咪唑的循环伏安特性。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3c27/9082764/dcdb95707974/c8ra05103h-f6.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3c27/9082764/202e15e35e13/c8ra05103h-f1.jpg
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