{"title":"Electricity-driven reductive coupling reaction of imines with N-(acyloxy)phthalimides","authors":"Xiaoye Liu, Leilei Feng","doi":"10.1016/j.tetlet.2024.155367","DOIUrl":null,"url":null,"abstract":"<div><div>The reductive coupling reaction between imines and <em>N</em>-(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 <em>in situ</em>. 4-Fluorobenzoic acid and <em>N</em>,<em>N</em>-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.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"153 ","pages":"Article 155367"},"PeriodicalIF":1.5000,"publicationDate":"2024-11-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Tetrahedron Letters","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S0040403924004623","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q3","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0
Abstract
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.
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.
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