{"title":"电化学 N-olefination 技术用于乙烯基唑的区域和立体选择性合成","authors":"Kejun Lin , Jianyong Lan , Lin Hao , Tingshun Zhu","doi":"10.1016/j.gresc.2024.01.005","DOIUrl":null,"url":null,"abstract":"<div><div>A selenium-catalyzed electrosynthesis involving regio- and stereo-selective <em>N</em>-olefination of azoles was developed. The room-temperature reaction was efficient (up to 97 % yield) and compatible with various styrenes and azoles. Mechanistic study showed that the cascade reaction was triggered by the selenium-cation-mediated electrophilic <em>trans-</em>aminoselenation, and followed by an oxidative <em>cis</em>-elimination of selane. The electrosynthesis was also well compatible with the more challenging internal alkene substrates, giving the desired <em>N</em>-vinyl azoles in up to 88 % yield and > 20:1 <em>Z/E</em> ratio.</div></div>","PeriodicalId":12794,"journal":{"name":"Green Synthesis and Catalysis","volume":"6 2","pages":"Pages 183-186"},"PeriodicalIF":0.0000,"publicationDate":"2025-05-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Electrochemical N-olefination for the regio- and stereo-selective synthesis of vinyl azoles\",\"authors\":\"Kejun Lin , Jianyong Lan , Lin Hao , Tingshun Zhu\",\"doi\":\"10.1016/j.gresc.2024.01.005\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><div>A selenium-catalyzed electrosynthesis involving regio- and stereo-selective <em>N</em>-olefination of azoles was developed. The room-temperature reaction was efficient (up to 97 % yield) and compatible with various styrenes and azoles. Mechanistic study showed that the cascade reaction was triggered by the selenium-cation-mediated electrophilic <em>trans-</em>aminoselenation, and followed by an oxidative <em>cis</em>-elimination of selane. The electrosynthesis was also well compatible with the more challenging internal alkene substrates, giving the desired <em>N</em>-vinyl azoles in up to 88 % yield and > 20:1 <em>Z/E</em> ratio.</div></div>\",\"PeriodicalId\":12794,\"journal\":{\"name\":\"Green Synthesis and Catalysis\",\"volume\":\"6 2\",\"pages\":\"Pages 183-186\"},\"PeriodicalIF\":0.0000,\"publicationDate\":\"2025-05-01\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Green Synthesis and Catalysis\",\"FirstCategoryId\":\"1085\",\"ListUrlMain\":\"https://www.sciencedirect.com/science/article/pii/S266655492400005X\",\"RegionNum\":0,\"RegionCategory\":null,\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"2024/1/12 0:00:00\",\"PubModel\":\"Epub\",\"JCR\":\"\",\"JCRName\":\"\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Green Synthesis and Catalysis","FirstCategoryId":"1085","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S266655492400005X","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"2024/1/12 0:00:00","PubModel":"Epub","JCR":"","JCRName":"","Score":null,"Total":0}
Electrochemical N-olefination for the regio- and stereo-selective synthesis of vinyl azoles
A selenium-catalyzed electrosynthesis involving regio- and stereo-selective N-olefination of azoles was developed. The room-temperature reaction was efficient (up to 97 % yield) and compatible with various styrenes and azoles. Mechanistic study showed that the cascade reaction was triggered by the selenium-cation-mediated electrophilic trans-aminoselenation, and followed by an oxidative cis-elimination of selane. The electrosynthesis was also well compatible with the more challenging internal alkene substrates, giving the desired N-vinyl azoles in up to 88 % yield and > 20:1 Z/E ratio.
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