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构建C-N键,在有机合成中占有非常重要的地位。本文介绍了一种简单、方便的合成芳香胺的方法。在100℃和二甲亚砜溶剂体系中,卤代芳烃分别和伯、仲两类胺在叔丁醇钾催化下经过1h反应,以45%~90%的收率,生成一系列芳香胺。方法进一步拓宽了叔丁醇钾催化的C-N交叉偶联反应的底物,并显示出独特的底物选择性,即对富电子卤代芳烃有很好的活性。据推测,本偶联反应是通过先形成苯炔中间体,再与胺发生交叉偶联的历程进行的。
C-N bond construction, in organic synthesis occupies a very important position. This article describes a simple and convenient method for the synthesis of aromatic amines. In 100 ℃ and dimethylsulfoxide solvent system, a series of aromatic amines were formed in 45% ~ 90% yields after halogenated aromatic hydrocarbons were respectively reacted with primary and secondary amines for 1h under potassium tert-butoxide catalysis. The method further broadens the potassium tert-butoxide-catalyzed C-N cross-coupling reaction substrate and exhibits unique substrate selectivity, ie, good activity for electron-rich halogenated aromatics. It is speculated that the coupling reaction was carried out by first forming a phenyne intermediate and then cross-coupling with the amine.