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 The Journal of Organic Chemistry Pub Date : 2024-04-03 DOI:10.1021/acs.joc.4c0002110.1021/acs.joc.4c00021
Zheng Zhu, Yanan Li*, Shitang Ma, Xuan Zhou, Yekai Huang, Jianan Sun* and Wei-Yi Ding*, 
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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.

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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。
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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.
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