Electrochemically Driven Site-Selective C(sp2)-H Bond Hydroxylation of N-Substituted Anilines

IF 4.4 2区 化学 Q2 CHEMISTRY, APPLIED Advanced Synthesis & Catalysis Pub Date : 2024-12-02 DOI:10.1002/adsc.202401349
Anil Dapkekar, Suman Kumar Nag, Gedu Satyanarayana
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Abstract

Organic synthesis has long been fascinated by phenolic compounds, especially their exploration of selectively hydroxylating arenes utilizing H2O as a hydroxyl source. However, phenols' low redox potential and strong reactivity frequently result in unwanted overoxidation byproducts. Here, we present an electrochemical strategy to overcome this difficulty by using electricity as an oxidant and facilitating the para-selective hydroxylation of N-protected anilines. This process exhibits excellent regio-selectivity, compatibility with diverse functional groups, and adaptability by handling an extensive range of substrates. Noteworthily, the technique provides a sustainable substitute for paracetamol synthesis and terminal acetylene-holding hydroxylated products, proving the suitability of this strategy for drug synthesis. Significantly, mechanistic investigations suggest the possible radical pathway and water as a hydroxyl source for this strategy.
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电化学驱动的n -取代苯胺的位点选择性C(sp2)-H键羟基化
有机合成一直被酚类化合物所吸引,特别是他们利用水作为羟基源选择性羟基化芳烃的探索。然而,苯酚的低氧化还原电位和强反应性经常导致不必要的过氧化副产物。在这里,我们提出了一种电化学策略来克服这一困难,即利用电作为氧化剂,促进n -保护苯胺的准选择性羟基化。该工艺表现出优异的区域选择性,与多种官能团的相容性,以及处理广泛底物的适应性。值得注意的是,该技术为扑热息痛合成和末端乙炔羟基化产物提供了可持续的替代品,证明了该策略在药物合成中的适用性。值得注意的是,机制研究表明可能的自由基途径和水作为这个策略的羟基来源。
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来源期刊
Advanced Synthesis & Catalysis
Advanced Synthesis & Catalysis 化学-应用化学
CiteScore
9.40
自引率
7.40%
发文量
447
审稿时长
1.8 months
期刊介绍: Advanced Synthesis & Catalysis (ASC) is the leading primary journal in organic, organometallic, and applied chemistry. The high impact of ASC can be attributed to the unique focus of the journal, which publishes exciting new results from academic and industrial labs on efficient, practical, and environmentally friendly organic synthesis. While homogeneous, heterogeneous, organic, and enzyme catalysis are key technologies to achieve green synthesis, significant contributions to the same goal by synthesis design, reaction techniques, flow chemistry, and continuous processing, multiphase catalysis, green solvents, catalyst immobilization, and recycling, separation science, and process development are also featured in ASC. The Aims and Scope can be found in the Notice to Authors or on the first page of the table of contents in every issue.
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