Discovery of 2-(pyridin-2-yl)aniline as a directing group for the sp2 C–H bond amination mediated by cupric acetate,Organic & Biomolecular Chemistry

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Discovery of 2-(pyridin-2-yl)aniline as a directing group for the sp2 C–H bond amination mediated by cupric acetate
Organic & Biomolecular Chemistry ( IF 2.9 ) Pub Date : 2017-07-24 00:00:00 , DOI: 10.1039/c7ob01353a
Hong-Yi Zhao _{1,

2,

3,

4,

5} , Hui-Yan Wang _{1,

2,

3,

4,

5} , Shuai Mao _{1,

2,

3,

4,

5} , Minhang Xin _{1,

2,

3,

4,

5} , Hao Zhang _{1,

2,

3,

4,

5} , San-Qi Zhang _{1,

2,

3,

4,

5}

Affiliation

2-(Pyridin-2-yl) aniline was designed as a new, removable directing group in promoting C–H amination mediated by cupric acetate. Employing this auxiliary, the β-C(sp²)–H bonds of benzamide derivatives can be effectively aminated with a variety of amines in moderate to good yields with good functional group tolerance in air. In addition, the quinazolinone derivatives were isolated from the reaction mixture of N-(2-(pyridin-2-yl)phenyl)benzamide with formamide or 5-nitroindole. The corresponding mechanism is discussed. These results indicate that 2-(pyridine-2-yl)aniline can serve as a directing group.

中文翻译：

发现2-（吡啶-2-基）苯胺作为乙酸铜介导的sp ² C–H键胺化的导向基团

2-（吡啶-2-基）苯胺被设计为一个新的可移动的导向基团，用于促进由乙酸铜介导的C–H胺化。使用这种辅助剂，苯甲酰胺衍生物的β-C（sp ²）–H键可以用各种胺有效地胺化，产率中等至良好，并且在空气中具有良好的官能团耐受性。另外，从N-（2-（吡啶-2-基）苯基）苯甲酰胺与甲酰胺或5-硝基吲哚的反应混合物中分离出喹唑啉酮衍生物。讨论了相应的机制。这些结果表明2-（吡啶-2-基）苯胺可以用作指导基团。

更新日期：2017-08-09

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