Xia-Die Wu,Xian-Bing Luo,Ru-Xi Hu,Meng-Yuan Wu,Zhifang Li,Zhong-Wei Hou,Lei Wang
{"title":"Electrochemical 1,5-Aryl Migration for Stereo- and Regioselective Synthesis of Tetrasubstituted Alkenes.","authors":"Xia-Die Wu,Xian-Bing Luo,Ru-Xi Hu,Meng-Yuan Wu,Zhifang Li,Zhong-Wei Hou,Lei Wang","doi":"10.1021/acs.orglett.5c02287","DOIUrl":null,"url":null,"abstract":"An electrochemical 1,5-aryl migration protocol for the stereo- and regioselective synthesis of Se-containing tetrasubstituted α,β-unsaturated amides has been developed. This approach leverages readily available N-benzylpropiolamides and diselenides as starting materials and proceeds without the need for oxidants or metal reagents. The simplicity of the protocol is further enhanced by its execution in a straightforward undivided electrolytic cell at room temperature, providing an efficient and innovative route for the synthesis of challenging tetrasubstituted alkenes.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"22 1","pages":""},"PeriodicalIF":5.0000,"publicationDate":"2025-07-10","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.5c02287","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
An electrochemical 1,5-aryl migration protocol for the stereo- and regioselective synthesis of Se-containing tetrasubstituted α,β-unsaturated amides has been developed. This approach leverages readily available N-benzylpropiolamides and diselenides as starting materials and proceeds without the need for oxidants or metal reagents. The simplicity of the protocol is further enhanced by its execution in a straightforward undivided electrolytic cell at room temperature, providing an efficient and innovative route for the synthesis of challenging tetrasubstituted alkenes.
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.