Metal-free tandem carbene N–H insertions and C–C bond cleavages,Chemical Science

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Metal-free tandem carbene N–H insertions and C–C bond cleavages
Chemical Science ( IF 7.6 ) Pub Date : 2020-11-10 , DOI: 10.1039/d0sc05763k
Pu Chen ₁ , Jiang Nan ₁ , Yan Hu ₁ , Yifan Kang ₁ , Bo Wang ₁ , Yangmin Ma ₁ , Michal Szostak _{1,

2}

Affiliation

A metal-free C–H [5 + 1] annulation reaction of 2-arylanilines with diazo compounds has been achieved, giving rise to two types of prevalent phenanthridines via highly selective C–C cleavage. Compared to the simple N–H insertion manipulation of diazo, this method elegantly accomplishes a tandem N–H insertion/S_EAr/C–C cleavage/aromatization reaction, and the synthetic utility of this new transformation is exemplified by the succinct syntheses of trisphaeridine and bicolorine alkaloids.

中文翻译：

无金属串联卡宾 N-H 插入和 C-C 键断裂

已经实现了 2-芳基苯胺与重氮化合物的无金属 C–H [5 + 1] 成环反应，通过高度选择性的 C–C 裂解产生两种常见的菲啶。与重氮的简单 N-H 插入操作相比，该方法优雅地完成了串联 N-H 插入/S _E Ar/C-C 裂解/芳构化反应，并且这种新转化的合成效用通过以下的简洁合成得到了例证： trisphaeridine 和 bicolorine 生物碱。

更新日期：2020-11-18

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