The development and study of a simple copper-catalyzed reaction of nitroarenes with aryl boronic acids to form diarylamines that uses phenyl silane as the stoichiometric terminal reductant is described. This cross-coupling reaction requires as little as 2 mol % of CuX and 4 mol % of diphosphine for success and tolerates a broad range of functional groups on either the nitroarene or the aryl boronic acid to afford the amine in good yield. Mechanistic investigations established that the cross-coupling reaction proceeds via a nitrosoarene intermediate and that copper is required to catalyze both the deoxygenation of the nitroarene to afford the nitrosoarene and C–NAr bond formation of the nitrosoarene with the aryl boronic acid.

中文翻译：

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Cu催化硝基芳烃与芳基硼酸交叉偶联构建二芳基胺

描述了使用苯基硅烷作为化学计量末端还原剂的硝基芳烃与芳基硼酸形成二芳基胺的简单铜催化反应的开发和研究。这种交叉偶联反应只需要 2 mol% 的 CuX 和 4 mol% 的二膦即可成功，并且可以容忍硝基芳烃或芳基硼酸上的多种官能团，从而以良好的收率提供胺。机理研究表明，交叉偶联反应通过亚硝基芳烃中间体进行，并且铜需要催化硝基芳烃的脱氧以提供亚硝基芳烃和亚硝基芳烃与芳基硼酸的 C-NAr 键形成。