Intermolecular Dearomative 1,2-Amination/Carbonylation via Nucleophilic Addition of Simple Amines to Arene π-Bonds
Intermolecular Dearomative 1,2-Amination/Carbonylation via Nucleophilic Addition of Simple Amines to Arene π-Bonds
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DOI：
10.1002/chem.202300776
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发表时间：
2023-05-08
影响因子：
4.3
通讯作者：
Li，Wei
中科院分区：
文献类型：
--
作者：
Li，Zheng-Jian;Wang，Ming-Yang;Li，Wei
在有机合成中，特殊氨基官能团的引入是至关重要的。与烯烃的成熟胺化方法相比，芳烃的脱芳胺化在很大程度上未被探索，这是由于芳烃π键的固有惰性反应性和选择性挑战。在此，我们报告了通过简单胺与铬结合的芳烃的直接亲核加成的分子间脱芳氨基官能化。这种多组分1，2-胺化/羰基化反应使得能够在无CO气体条件下从苯衍生物快速获得含有氨基和酰胺官能团的复杂脂环族化合物，这也代表了氮基亲核试剂在η6-配位诱导的芳烃脱芳构化中的首次应用。
The incorporation of the privileged amino functionality is of paramount importance in organic synthesis. In contrast to the well‐developed amination methods for alkenes, the dearomative amination of arenes is largely underexplored due to the inherently inert reactivity of arene π‐bonds and selectivity challenges. Herein, we report an intermolecular dearomative aminofunctionalization via direct nucleophilic addition of simple amines to chromium‐bound arenes. This multicomponent 1,2‐amination/carbonylation reaction enables rapid access to complicated alicyclic compounds containing amino and amide functionalities from benzene derivatives under CO‐gas‐free conditions, which also represents the first application of nitrogen‐based nucleophiles in η6‐coordination‐induced arene dearomatizations.