Cu-Catalyzed Aerobic Oxidative N–N Coupling of Carbazoles and Diarylamines Including Selective Cross-Coupling,Journal of the American Chemical Society

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Cu-Catalyzed Aerobic Oxidative N–N Coupling of Carbazoles and Diarylamines Including Selective Cross-Coupling
Journal of the American Chemical Society ( IF 14.4 ) Pub Date : 2018-07-10 , DOI: 10.1021/jacs.8b05245
Michael C Ryan ₁ , Joseph R Martinelli ₂ , Shannon S Stahl ₁

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A Cu-catalyzed method has been identified for aerobic oxidative dimerization of carbazoles and diarylamines to the corresponding N-N coupled bicarbazoles and tetraarylhydrazines. The reactions proceed under mild conditions (1 atm O2, 60-80 °C) with a catalyst composed of CuBr·dimethylsulfide and N, N-dimethylaminopyridine. Reactions between carbazole and diarylamines show unusually selective cross-coupling, even with a 1:1 ratio of the two substrates. This behavior was found to arise from reversible formation of the tetraarylhydrazine. Formation of this species is kinetically favored, but cleavage of the N-N bond under the reaction conditions leads to selective formation of the thermodynamically favored cross-coupling product.

中文翻译：

铜催化咔唑和二芳胺的有氧氧化 N-N 偶联，包括选择性交叉偶联

已经确定了一种铜催化方法，用于将咔唑和二芳基胺有氧氧化二聚成相应的 NN 偶联联咔唑和四芳基肼。该反应在温和条件（1 atm O2，60-80 °C）下进行，催化剂由 CuBr·二甲基硫醚和 N,N-二甲基氨基吡啶组成。咔唑和二芳基胺之间的反应显示出异常选择性的交叉偶联，即使两种底物的比例为 1:1。发现这种行为是由四芳基肼的可逆形成引起的。该物质的形成在动力学上是有利的，但反应条件下 NN 键的断裂会导致热力学上有利的交叉偶联产物的选择性形成。

更新日期：2018-07-10

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