Qiang Zhong , Xinru Jiang , Hui Gao , Pei-Long Wang , Hongji Li
{"title":"通过电化学亚磺酰基生成技术实现无保护 N-杂环的区域选择性亚磺酰化","authors":"Qiang Zhong , Xinru Jiang , Hui Gao , Pei-Long Wang , Hongji Li","doi":"10.1039/d4qo01772b","DOIUrl":null,"url":null,"abstract":"<div><div>An electrochemical sulfenylation of unprotected <em>N</em>-heterocycles with a wide range of commercially available arylsulfonyl chlorides was developed. This protocol features the use of inexpensive <em>N</em>,<em>N</em>,<em>N</em>′,<em>N</em>’-tetramethylethylenediamine (TMEDA) serving as both a promoter and a base to tune the sulfenylation process, thus affording sulfenylated products in good yields with high regioselectivity. Importantly, TMEDA significantly lowers the oxidation potential of indole, thus avoiding the over-oxidation of indole.</div></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"12 2","pages":"Pages 684-689"},"PeriodicalIF":0.0000,"publicationDate":"2024-11-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"TMEDA-enabled regioselective sulfenylation of unprotected N-heterocycles via electrochemical sulfinyl radical generation†\",\"authors\":\"Qiang Zhong , Xinru Jiang , Hui Gao , Pei-Long Wang , Hongji Li\",\"doi\":\"10.1039/d4qo01772b\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><div>An electrochemical sulfenylation of unprotected <em>N</em>-heterocycles with a wide range of commercially available arylsulfonyl chlorides was developed. This protocol features the use of inexpensive <em>N</em>,<em>N</em>,<em>N</em>′,<em>N</em>’-tetramethylethylenediamine (TMEDA) serving as both a promoter and a base to tune the sulfenylation process, thus affording sulfenylated products in good yields with high regioselectivity. Importantly, TMEDA significantly lowers the oxidation potential of indole, thus avoiding the over-oxidation of indole.</div></div>\",\"PeriodicalId\":94379,\"journal\":{\"name\":\"Organic chemistry frontiers : an international journal of organic chemistry\",\"volume\":\"12 2\",\"pages\":\"Pages 684-689\"},\"PeriodicalIF\":0.0000,\"publicationDate\":\"2024-11-19\",\"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/S2052412924008064\",\"RegionNum\":0,\"RegionCategory\":null,\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"2024/11/27 0:00:00\",\"PubModel\":\"Epub\",\"JCR\":\"\",\"JCRName\":\"\",\"Score\":null,\"Total\":0}","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/S2052412924008064","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"2024/11/27 0:00:00","PubModel":"Epub","JCR":"","JCRName":"","Score":null,"Total":0}
TMEDA-enabled regioselective sulfenylation of unprotected N-heterocycles via electrochemical sulfinyl radical generation†
An electrochemical sulfenylation of unprotected N-heterocycles with a wide range of commercially available arylsulfonyl chlorides was developed. This protocol features the use of inexpensive N,N,N′,N’-tetramethylethylenediamine (TMEDA) serving as both a promoter and a base to tune the sulfenylation process, thus affording sulfenylated products in good yields with high regioselectivity. Importantly, TMEDA significantly lowers the oxidation potential of indole, thus avoiding the over-oxidation of indole.
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