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首页> 外文期刊>Chemistry: A European journal >Reactions Catalysed by a Binuclear Copper Complex: Aerobic Cross Dehydrogenative Coupling of N-Aryl Tetrahydroisoquinolines
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Reactions Catalysed by a Binuclear Copper Complex: Aerobic Cross Dehydrogenative Coupling of N-Aryl Tetrahydroisoquinolines

机译：由双核铜复合物催化的反应：N-芳基四羟基异喹啉的有氧交叉脱氢偶联偶联

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摘要

Binuclear copper complex [{Cu(Sal)_2(NCMe)}_2] (Sal=salicylate) was found to be an active catalyst for the aerobic oxidation of N-aryl tetrahydroisoquinolines to the corresponding iminium ions, which could be trapped by a wide range of nucleophiles to form coupled products. The reactions took place under 1 bar of O_2 at room temperature with 1 mol% of the copper catalyst being sufficient in most cases, and are considerably accelerated by catalytic chloride anions. Mechanistic studies show that the Cu~(II) dimer oxidizes the amine to the iminium ion, and this two-electron process requires O_2, whereby the resulting Cu~I is concomitantly reoxidised back to Cu~(II). Various lines of evidence suggest that the oxidative coupling reaction is turnover-limited by the step of iminium formation, and it is this step that is promoted by the chloride anion. Since it is more efficient than and mechanistically distinct from the well-studied simple copper salts such as CuBr and CuCl_2, the binuclear copper catalyst provides a new tool for oxidative coupling reactions.
机译：发现双核铜络合物[{Cu（SAL）_2（NCME）} _ 2]（Sal =水杨酸盐）是用于N-芳基四碳异喹啉的有氧氧化至相应的亚胺离子的活性催化剂，这可能被广泛捕获形成偶联产品的亲核试剂系列。在大多数情况下，在室温下在室温下的1摩尔铜催化剂的1摩尔％的铜催化剂中发生反应，并且通过催化氯离阴离子大大加速。机械研究表明，Cu〜（II）二聚体将胺氧化给亚胺离子，并且该双电子过程需要O_2，由此得到的Cu〜I伴随着再氧化回Cu〜（II）。各种证据表明，氧化偶联反应是由亚胺形成步骤的转换限制，并且是氯化物阴离子促进的该步骤。由于它比从研究的简单的简单铜盐如CUBR和CuCl_2更高的效率和机械地不同，因此双核铜催化剂提供了一种用于氧化偶联反应的新工具。

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  • 来源
    《Chemistry: A European journal》 |2017年第13期|共11页
  • 作者

    Yuxia Liu; Chao Wang; Dong Xue; Miao Xiao; Chaoqun Li; Jianliang Xiao;

  • 作者单位

    Key Laboratory of Applied Surface and Colloid Chemistry Ministry of Education and School of Chemistry and Chemical Engineering Shaanxi Normal University Xi'an 710062 (P. R. China);

    Key Laboratory of Applied Surface and Colloid Chemistry Ministry of Education and School of Chemistry and Chemical Engineering Shaanxi Normal University Xi'an 710062 (P. R. China);

    Key Laboratory of Applied Surface and Colloid Chemistry Ministry of Education and School of Chemistry and Chemical Engineering Shaanxi Normal University Xi'an 710062 (P. R. China);

    Key Laboratory of Applied Surface and Colloid Chemistry Ministry of Education and School of Chemistry and Chemical Engineering Shaanxi Normal University Xi'an 710062 (P. R. China);

    Key Laboratory of Applied Surface and Colloid Chemistry Ministry of Education and School of Chemistry and Chemical Engineering Shaanxi Normal University Xi'an 710062 (P. R. China);

    Key Laboratory of Applied Surface and Colloid Chemistry Ministry of Education and School of Chemistry and Chemical Engineering Shaanxi Normal University Xi'an 710062 (P. R. China);

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  • 原文格式 PDF
  • 正文语种 eng
  • 中图分类 应用化学;
  • 关键词

    copper; cross-coupling; homogeneous catalysis; oxidation; reaction mechanisms;

    机译：铜;交叉偶联;均匀催化;氧化;反应机制;

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