Site-selective benzylic C–H oxidation through mediated electrolysis

IF 17.7 1区 化学 Q1 CHEMISTRY, APPLIED Chinese Journal of Catalysis Pub Date : 2024-12-01 Epub Date: 2024-12-03 DOI:10.1016/S1872-2067(24)60139-7
Yi-Fan Xi , Rui-Xing Gao , Ping Fang , Ya-Ping Han , Cong Ma , Tian-Sheng Mei
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Abstract

A novel strategy for site-selective benzylic C–H oxidation has been developed through mediated electrolysis. A bulky maleimide N-oxyl radical (MINO) generated by proton-coupled electrochemical oxidation of N-hydroxymaleimide (NHMI), serves as a hydrogen atom-transfer mediator. Good-to-excellent site selectivity was observed among different substrates, providing a practical approach for site-selective benzylic C–H oxidation. Additionally, the hydrogen-atom transfer mechanism for C–H electrochemical oxidation allows the oxidation to proceed at much lower anode potentials relative to direct electrolysis and with minimal reliance on the substrate's electronic properties.
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通过电解介导的位点选择性苯C-H氧化
通过介导的电解,开发了一种新的位点选择性苯基C-H氧化策略。n-羟基马来酰亚胺(NHMI)通过质子偶联电化学氧化生成体积较大的马来酰亚胺n-氧自由基(MINO),作为氢原子转移介质。在不同的底物之间观察到良好到优异的位点选择性,为选择性氧化苯基C-H提供了实用的方法。此外,C-H电化学氧化的氢原子转移机制允许氧化在相对于直接电解低得多的阳极电位下进行,并且对衬底的电子特性依赖最小。
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来源期刊
Chinese Journal of Catalysis
Chinese Journal of Catalysis 工程技术-工程:化工
CiteScore
25.80
自引率
10.30%
发文量
235
审稿时长
1.2 months
期刊介绍: The journal covers a broad scope, encompassing new trends in catalysis for applications in energy production, environmental protection, and the preparation of materials, petroleum chemicals, and fine chemicals. It explores the scientific foundation for preparing and activating catalysts of commercial interest, emphasizing representative models.The focus includes spectroscopic methods for structural characterization, especially in situ techniques, as well as new theoretical methods with practical impact in catalysis and catalytic reactions.The journal delves into the relationship between homogeneous and heterogeneous catalysis and includes theoretical studies on the structure and reactivity of catalysts.Additionally, contributions on photocatalysis, biocatalysis, surface science, and catalysis-related chemical kinetics are welcomed.
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