Electrochemical Cross-Coupling between N-(4-Hydroxyphenyl)-sulfonamides and 2-Naphthols: Synthesis of 2,2′-Bis(arenol)s

IF 3.3 2区 化学 Q1 CHEMISTRY, ORGANIC
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,&nbsp;Yanan Li*,&nbsp;Shitang Ma,&nbsp;Xuan Zhou,&nbsp;Yekai Huang,&nbsp;Jianan Sun* and Wei-Yi Ding*,&nbsp;","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.

Abstract Image

N-(4-羟基苯基)-磺酰胺与 2-萘酚的电化学交叉偶联:2,2′-双萘酚的合成
我们在此介绍一种电化学方法,用于 N-(4-羟基苯基)-磺酰胺和 2-萘酚的脱氢交叉偶联。这种转化提供了一种直接和可扩展的方法,可在温和的条件下以中等到较高的产率获得多种 C1 对称的 2,2′-双(萘酚)。该反应的不对称变体也进行了初步尝试,合成 2,2′-双(壬醇)的ee值≤55%。通过对照实验,提出了该反应的合理机理。
本文章由计算机程序翻译,如有差异,请以英文原文为准。
求助全文
约1分钟内获得全文 求助全文
来源期刊
The Journal of Organic Chemistry
The Journal of Organic Chemistry 化学-有机化学
CiteScore
6.20
自引率
11.10%
发文量
1467
审稿时长
2 months
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.
×
引用
GB/T 7714-2015
复制
MLA
复制
APA
复制
导出至
BibTeX EndNote RefMan NoteFirst NoteExpress
×
提示
您的信息不完整,为了账户安全,请先补充。
现在去补充
×
提示
您因"违规操作"
具体请查看互助需知
我知道了
×
提示
确定
请完成安全验证×
copy
已复制链接
快去分享给好友吧!
我知道了
右上角分享
点击右上角分享
0
联系我们:info@booksci.cn Book学术提供免费学术资源搜索服务,方便国内外学者检索中英文文献。致力于提供最便捷和优质的服务体验。 Copyright © 2023 布克学术 All rights reserved.
京ICP备2023020795号-1
ghs 京公网安备 11010802042870号
Book学术文献互助
Book学术文献互助群
群 号:481959085
Book学术官方微信