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Aerobic and electrochemical oxidative cross-dehydrogenative-coupling (CDC) reaction in an imidazolium-based ionic liquid

机译:咪唑鎓离子液体中的需氧和电化学氧化交叉脱氢偶联(CDC)反应

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摘要

The ionic liquid 1-butyl-3methylimidazolium tetrafluoroborate [BMIm][BF_4] has demonstrated high efficiency when applied as a solvent in the oxidative nitro-Mannich carboncarbon bond formation. The coppercatalyzed cross-dehydrogenative coupling (CDC) between N-phenyltetrahydroisoquinoline and nitromethane in [BMIm][BF_4] occurred with high yield under the described reaction conditions. Both the ionic liquid and copper catalyst were recycled nine times with almost no lost of activity. The electrochemical behavior of the tertiary amine substrate and β-nitroamine product was investigated employing [BMIm][BF_4] as electrolyte solvent. The potentiostatic electrolysis in ionic liquid afforded the desired product with a high yield. This result and the cyclic voltammetric investigation provide a better understanding of the reaction mechanism, which involves radical and iminium cation intermediates.
机译:离子液体四氟硼酸1-丁基-3-甲基咪唑鎓[BMIm] [BF_4]在氧化硝基-曼尼希碳碳键的形成中用作溶剂时表现出很高的效率。在上述反应条件下,[BMIm] [BF_4]中N-苯基四氢异喹啉和硝基甲烷之间的铜催化交叉脱氢偶联(CDC)发生。离子液体催化剂和铜催化剂都循环了九次,几乎没有活性损失。以[BMIm] [BF_4]为电解质溶剂研究了叔胺底物和β-硝胺产物的电化学行为。在离子液体中的恒电位电解以高收率提供了所需的产物。该结果和循环伏安法研究提供了对反应机理的更好理解,其中涉及自由基和亚胺阳离子中间体。

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