Halogen‐Bond‐Promoted α‐C−H Amination of Ethers for the Synthesis of Hemiaminal Ethers,Advanced Synthesis & Catalysis

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Halogen‐Bond‐Promoted α‐C−H Amination of Ethers for the Synthesis of Hemiaminal Ethers
Advanced Synthesis & Catalysis ( IF 4.4 ) Pub Date : 2018-03-12 , DOI: 10.1002/adsc.201800006
Zhangjin Pan ₁ , Zhenwei Fan ₁ , Beili Lu ₂ , Jiajia Cheng _{1,

3}

Affiliation

A simple halogen‐bond‐promoted α‐C−H amination of ether/thioether with a variety of N−H compounds has been accomplished. In the presence of low‐cost and readily available perfluorobutyl iodide, a diverse range of hemiaminal ether derivatives, including the valuable hydrazone hemiaminal ethers, were quickly assembled under thermal or visible‐light irradiation conditions. Mechanistic studies suggest that a halogen‐bond adduct was formed and a radical chain pathway might be operative. Synthetic application of the method has been demonstrated via the preparation of the anti‐viral and anti‐tumor drug, Tegafur.

中文翻译：

卤素键促进的α-C-H醚化胺用于合成半羟色胺

已经完成了醚/硫醚与各种NH化合物的卤素键促进的简单α-CH胺化反应。在存在低成本且易于获得的全氟丁基碘的情况下，在热或可见光辐照条件下，迅速组装了各种各样的半胱氨酸醚衍生物，包括有价值的半胱氨酸醚。机理研究表明，形成了卤素键加合物，自由基链途径可能起作用。通过制备抗病毒和抗肿瘤药物替加福证明了该方法的综合应用。

更新日期：2018-03-12

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