Zheng Zhu, Yanan Li*, Shitang Ma, Xuan Zhou, Yekai Huang, Jianan Sun* and Wei-Yi Ding*,
{"title":"Electrochemical Cross-Coupling between N-(4-Hydroxyphenyl)-sulfonamides and 2-Naphthols: Synthesis of 2,2′-Bis(arenol)s","authors":"Zheng Zhu, Yanan Li*, Shitang Ma, Xuan Zhou, Yekai Huang, Jianan Sun* and Wei-Yi Ding*, ","doi":"10.1021/acs.joc.4c0002110.1021/acs.joc.4c00021","DOIUrl":null,"url":null,"abstract":"<p >We herein present an electrochemical method for the dehydrogenative cross-coupling of <i>N</i>-(4-hydroxyphenyl)-sulfonamides and 2-naphthols. This transformation provides a direct and scalable approach to a wide range of <i>C</i><sub>1</sub>-symmetric 2,2′-bis(arenol)s with moderate to high yields under mild conditions. Preliminary attempts with the asymmetric variant of this reaction were also performed with ≤55% ee for the synthesis of 2,2′-bis(arenol)s. Control experiments were conducted to propose a plausible mechanism for the reaction.</p>","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":"89 22","pages":"16185–16194 16185–16194"},"PeriodicalIF":3.3000,"publicationDate":"2024-04-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"The Journal of Organic Chemistry","FirstCategoryId":"1","ListUrlMain":"https://pubs.acs.org/doi/10.1021/acs.joc.4c00021","RegionNum":2,"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
We herein present an electrochemical method for the dehydrogenative cross-coupling of N-(4-hydroxyphenyl)-sulfonamides and 2-naphthols. This transformation provides a direct and scalable approach to a wide range of C1-symmetric 2,2′-bis(arenol)s with moderate to high yields under mild conditions. Preliminary attempts with the asymmetric variant of this reaction were also performed with ≤55% ee for the synthesis of 2,2′-bis(arenol)s. Control experiments were conducted to propose a plausible mechanism for the reaction.
期刊介绍:
The Journal of Organic Chemistry welcomes original contributions of fundamental research in all branches of the theory and practice of organic chemistry. In selecting manuscripts for publication, the editors place emphasis on the quality and novelty of the work, as well as the breadth of interest to the organic chemistry community.