Xiaoman Li , Jiawei Huang , Ji-Xing Zhao , Liang Xu , Ping Liu , Jichang Liu , Yu Wei
{"title":"Electrochemical strategies for N-alkylation and N-acylation of NH-sulfoximines via the decarboxylation and deoxygenation of carboxylic acids†","authors":"Xiaoman Li , Jiawei Huang , Ji-Xing Zhao , Liang Xu , Ping Liu , Jichang Liu , Yu Wei","doi":"10.1039/d5qo00068h","DOIUrl":null,"url":null,"abstract":"<div><div>The functionalization of NH-sulfoximines to construct N–C bonds from common carboxylic acids remains underdeveloped. Herein, electrochemical strategies were utilized to enable the chemoselective decarboxylation or deoxygenation of carboxylic acids for the synthesis of <em>N</em>-alkyl and <em>N</em>-acyl sulfoximines. The advantages of these methods include mild reaction conditions, no electrode sacrifice, no external oxidants or metal catalysts, and easy scalability to gram-scale production. Furthermore, 67 diverse sulfoximine derivatives, particularly those incorporating motifs from amino acids and drug molecules, were obtained.</div></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"12 11","pages":"Pages 3445-3453"},"PeriodicalIF":0.0000,"publicationDate":"2025-03-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic chemistry frontiers : an international journal of organic chemistry","FirstCategoryId":"1085","ListUrlMain":"https://www.sciencedirect.com/org/science/article/pii/S2052412925001883","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"","JCRName":"","Score":null,"Total":0}
引用次数: 0
Abstract
The functionalization of NH-sulfoximines to construct N–C bonds from common carboxylic acids remains underdeveloped. Herein, electrochemical strategies were utilized to enable the chemoselective decarboxylation or deoxygenation of carboxylic acids for the synthesis of N-alkyl and N-acyl sulfoximines. The advantages of these methods include mild reaction conditions, no electrode sacrifice, no external oxidants or metal catalysts, and easy scalability to gram-scale production. Furthermore, 67 diverse sulfoximine derivatives, particularly those incorporating motifs from amino acids and drug molecules, were obtained.