Dual Nickel/Photoredox-Catalyzed Synthesis of N-formyl N,N’-Diaryl Ethylenediamines via Multiple C−N/C−C Coupling of Nitroarenes with Trimethylamine,Advanced Synthesis & Catalysis

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Dual Nickel/Photoredox-Catalyzed Synthesis of N-formyl N,N’-Diaryl Ethylenediamines via Multiple C−N/C−C Coupling of Nitroarenes with Trimethylamine
Advanced Synthesis & Catalysis ( IF 4.4 ) Pub Date : 2023-06-20 , DOI: 10.1002/adsc.202300431
Tongtong Zheng ₁ , Zhe Feng ₂ , Jun-An Ma ₂ , Chi Wai Cheung ₁

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N,N’-Diaryl ethylenediamines are common feedstocks in organic synthesis and important structural motifs in medicinal chemistry. Whereas the C−N formation reactions based on anilines and aryl halides are the most direct methods to access N,N’-diaryl ethylenediamines, the photocatalytic synthetic version remains undeveloped. Herein we describe the dual nickel/photoredox-catalyzed amination reaction using nitroarenes and trimethylamine as reaction substrates. This cascade transformation hinges on the multiple C−N and C−C coupling events based on the nitrogen radical and α-aminomethyl radical derived from nitroarene and trimethylamine, respectively. A variety of N-formyl N,N’-diaryl ethylenediamines can be obtained under the reaction protocol. Subsequent hydrolysis offers the N,N’-diaryl ethylenediamines for further derivatizations.

中文翻译：

双镍/光氧化还原催化硝基芳烃与三甲胺多重 C−N/C−C 偶联合成 N-甲酰基 N,N'-二芳基乙二胺

N , N'-二芳基乙二胺是有机合成中的常见原料，也是药物化学中的重要结构基序。虽然基于苯胺和芳基卤化物的 CN-N 形成反应是获得N , N'-二芳基乙二胺的最直接方法，但光催化合成方法仍未开发。在此，我们描述了使用硝基芳烃和三甲胺作为反应底物的双镍/光氧化还原催化的胺化反应。这种级联转化取决于分别基于硝基芳烃和三甲胺衍生的氮自由基和α-氨甲基自由基的多个CN和CC耦合事件。各种N-甲酰基N , N'-二芳基乙二胺可以根据该反应方案获得。随后的水解提供N , N'-二芳基乙二胺用于进一步衍生化。

更新日期：2023-06-20

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