亚胺与 N-(酰氧基)邻苯二甲酰亚胺的电驱动还原偶联反应

IF 1.5 4区化学 Q3 CHEMISTRY, ORGANIC Tetrahedron Letters Pub Date : 2024-11-14 DOI:10.1016/j.tetlet.2024.155367

Xiaoye Liu, Leilei Feng

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引用次数: 0

摘要

我们开发了电化学条件下亚胺与 N-（酰氧基）邻苯二甲酰亚胺（NHPI 酯）的还原偶联反应。该反应体系温和，操作简便，无需金属参与，而且亚胺可由醛类和胺类原位生成。对氟苯甲酸和 N,N-二异丙基乙胺（DIPEA）都能提高反应效率，而且这两种试剂形成的离子对可以避免使用电解质。机理实验验证了烷基自由基中间体的形成，并结合循环伏安实验的结果，判断该反应经历了自由基加成的过程。

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Electricity-driven reductive coupling reaction of imines with N-(acyloxy)phthalimides

The reductive coupling reaction between imines and N-(acyloxy)phthalimides (NHPI esters) under electrochemical conditions has been developed. The reaction system was mild and easy to operate without the involvement of metals, and the imines could be generated from aldehydes and amines in situ. 4-Fluorobenzoic acid and N,N-diisopropylethanamine (DIPEA) could both improve the reaction efficiency, and the ion pair formed by these two reagents could avoid the use of electrolytes. The mechanism experiments verified the formation of alkyl radical intermediates, and combined with the results of cyclic voltammetry experiments, it was judged that the reaction underwent the process of radical addition.

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来源期刊

Tetrahedron Letters 化学-有机化学

CiteScore

3.50

自引率

5.60%

发文量

521

审稿时长

28 days

期刊介绍： Tetrahedron Letters provides maximum dissemination of outstanding developments in organic chemistry. The journal is published weekly and covers developments in techniques, structures, methods and conclusions in experimental and theoretical organic chemistry. Rapid publication of timely and significant research results enables researchers from all over the world to transmit quickly their new contributions to large, international audiences.