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A direct synthetic method for (nitronyl nitroxide)-substituted π-electronic compounds via a palladium-catalyzed cross-coupling reaction with a zinc complex†
Materials Chemistry Frontiers ( IF 7 ) Pub Date : 2018-01-18 00:00:00 , DOI: 10.1039/c7qm00565b
Shuichi Suzuki 1, 2, 3, 4, 5 , Fumiya Nakamura 1, 2, 3, 4, 5 , Takeshi Naota 1, 2, 3, 4, 5
Affiliation  

We have developed an efficient synthetic method for (nitronyl nitroxide)-substituted (NN-substituted) π-electronic compounds via palladium-catalyzed cross-coupling reactions with a zinc complex of the parent nitronyl nitroxide radical anion. Various aryl iodides can be directly converted to the desired coupling compounds with high efficiency. The utility of the present method has been demonstrated by direct synthesis of a newly prepared radical species, NN-substituted phenothiazine 15P, which could not be obtained from the corresponding aldehyde compound by typical condensation-oxidation methods. The molecular structure and characteristic electronic nature of 15P were examined by single-crystal X-ray diffraction analysis and cyclic voltammetry, indicating that 15P is a promising candidate as a precursor for a triplet ground state species by one-electron oxidation.

中文翻译:

通过钯催化与锌配合物的交叉偶联反应 直接合成(硝基亚硝酰氮)取代的π电子化合物的方法

我们已经开发了一种有效的合成方法,该方法可通过钯催化的与母硝酰基硝基氧自由基阴离子的锌络合物的交叉偶联反应来合成(硝酰基硝基氧)取代的(NN取代的)π电子化合物。各种芳基碘化物可以高效地直接转化为所需的偶联化合物。通过直接合成新制备的自由基物种NN取代的吩噻嗪15P证明了本方法的实用性,该自由基物种无法通过典型的缩合氧化方法从相应的醛化合物中获得。15P的分子结构和特征电子性质通过单晶X射线衍射分析和循环伏安法进行了检测,结果表明15P是通过单电子氧化成为三重态基态物质的前体的有前途的候选物。
更新日期:2018-01-18
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