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

IF 4.6 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Chemistry Frontiers Pub Date : 2024-11-27 DOI:10.1039/d4qo01772b

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":"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.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"25 1","pages":""},"PeriodicalIF":4.6000,"publicationDate":"2024-11-27","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\":\"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.\",\"PeriodicalId\":97,\"journal\":{\"name\":\"Organic Chemistry Frontiers\",\"volume\":\"25 1\",\"pages\":\"\"},\"PeriodicalIF\":4.6000,\"publicationDate\":\"2024-11-27\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Organic Chemistry Frontiers\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://doi.org/10.1039/d4qo01772b\",\"RegionNum\":1,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q1\",\"JCRName\":\"CHEMISTRY, ORGANIC\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic Chemistry Frontiers","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1039/d4qo01772b","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

摘要

本研究开发了一种电化学亚磺酰化方法，利用多种市售芳基磺酰氯对未受保护的 N-杂环进行亚磺酰化。该方案的特点是使用廉价的 N,N,N′,N'-四甲基乙二胺（TMEDA）作为促进剂和碱来调节亚磺酰化过程，从而以良好的产率和高区域选择性获得亚磺酰化产物。重要的是，TMEDA 大大降低了吲哚的氧化电位，从而避免了吲哚的过度氧化。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

TMEDA-enabled regioselective sulfenylation of unprotected N-heterocycles via electrochemical sulfinyl radical generation

查看原文本刊更多论文

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.

求助全文

通过发布文献求助，成功后即可免费获取论文全文。去求助

来源期刊

Organic Chemistry Frontiers CHEMISTRY, ORGANIC-

CiteScore

7.90

自引率

11.10%

发文量

686

审稿时长

1 months

期刊介绍： Organic Chemistry Frontiers is an esteemed journal that publishes high-quality research across the field of organic chemistry. It places a significant emphasis on studies that contribute substantially to the field by introducing new or significantly improved protocols and methodologies. The journal covers a wide array of topics which include, but are not limited to, organic synthesis, the development of synthetic methodologies, catalysis, natural products, functional organic materials, supramolecular and macromolecular chemistry, as well as physical and computational organic chemistry.