Dong Wang, Qiulu Wang, Mingxia Liu, Zihan Liu, Zixuan Wang, Wenhui Ji, Yu Wang, Jin Wang
{"title":"Synthesis of Primary and Secondary Amines via Electrochemical Reduction of Hydrazines","authors":"Dong Wang, Qiulu Wang, Mingxia Liu, Zihan Liu, Zixuan Wang, Wenhui Ji, Yu Wang, Jin Wang","doi":"10.1021/acs.orglett.4c04040","DOIUrl":null,"url":null,"abstract":"We herein introduce an electrochemical route for the N–N bond cleavage of hydrazines. This mild and green methodology utilized readily available mono- and 1,1-disubstituted hydrazines or their HCl salts as starting materials to access a broad scope of primary and secondary amines in high yields. The mechanistic investigation suggests that the amine product is formed by consecutive SET reduction, and utilization of a hydrazine HCl salt is important for providing sufficient conductivity and acidity to facilitate this reaction.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"91 1","pages":""},"PeriodicalIF":4.9000,"publicationDate":"2024-12-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic Letters","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1021/acs.orglett.4c04040","RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0
Abstract
We herein introduce an electrochemical route for the N–N bond cleavage of hydrazines. This mild and green methodology utilized readily available mono- and 1,1-disubstituted hydrazines or their HCl salts as starting materials to access a broad scope of primary and secondary amines in high yields. The mechanistic investigation suggests that the amine product is formed by consecutive SET reduction, and utilization of a hydrazine HCl salt is important for providing sufficient conductivity and acidity to facilitate this reaction.
期刊介绍:
Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.