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Organo-electroreduction enables arylcarboxylation of styrenes

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Science China Chemistry 2024年第11期67卷 3825-3832页

作者： Yanwei Wang Qian Wang Zile Zhu Weikang Qi youai qiu State Key Laboratory and Institute of Elemento-Organic Chemistry Frontiers Science Center for New Organic MatterHaihe Laboratory of Sustainable Chemical TransformationsCollege of ChemistryNankai UniversityTianjin 300071China

Electroreduction offers an alternative to generate high active intermediates from electrophiles(halides, alkenes, etc.) in organic synthesis. However, it still remains challenge to enable the transformations in controlled fashion for substrates with similar reduction potentials. Herein, an electroreductive arylcarboxylation of styrenes with aryl halides and CO_(2)promoted by an organomediator has been developed. The reaction exhibits the remarkable reactivity control between styrenes and aryl halides bearing very similar reduction potentials, which is enabled by the addition of a simple organic mediator. The mediated process for different kinds of aryl halides(iodides and bromides) could be achieved by simply tuning the electronic effect of the skeleton of naphthalene. This protocol displays a broad substrate scope and the extension to late-stage modification of biorelevant molecules and their derivatives showed a bright prospect. Moreover, density functional theory(DFT) calculations and mechanistic studies have been conducted and provide solid support to rationalize the selectivity and reactivity control observed.

关键词： CO_(2)utilization reductive organo-mediator carboxylation electroreduction aryl halides

Recent Advances in Photochemical/Electrochemical Carboxylation of Olefins with CO_(2)

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Chinese Journal of Chemistry 2024年第18期42卷 2249-2266页

作者： Qian Wang Yanwei Wang Min Liu Ganghui Chu youai qiu Xinjiang Laboratory of Native Medicinal and Edible Plant Resources Chemistry College of Chemistry and Environmental ScienceKashi UniversityKashiXinjiang 844000China state Key Laboratory and Institute of Elemento-Organic Chemistry Frontiers Science Centerfor New Organic MatterCollege of Chemistry Nankai University94 Weijin RoadTianjin 300071China

CO_(2) is an abundant,nontoxic,and renewable C1 feedstock in synthetic *** carboxylation of readily available olefins incorporating CO_(2) is regarded as a promising strategy to access high value-added carboxylic acids as well as CO_(2) ***,due to the thermodynamic stability and kinetic inertness of CO_(2) and the difficulty in controlling the regioselectivity,the carboxylation of olefins with CO_(2) still remains ***-type functionalization with olefins represented a powerful protocol and enabled the development of novel transformations in this *** recently,the advance of new technology,such as photoredox catalysis and the renaissance of electrochemistry in organic synthesis,offered access to unique chemical reactivities of radical precursors and provided new solutions to the functionalization of olefins.

关键词： CO_(2) Carboxylation Olefins Photocatalysis Electrocatalysis Radical Reduction Difunctionalization

Selective nickel-electrocatalyzed benzylic C-H oxygenation of functionalized alkyl arenes

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Chinese Chemical Letters 2024年第2期35卷 396-401页

作者： Shunyao Tang Siyi Wang Dongmei Zhang Xinxing Zhang Guang Yang Yanwei Wang youai qiu State Key Laboratory of Elemento-Organic Chemistry Frontiers Science Center for New Organic MatterCollege of ChemistryNankai UniversityTianjin 300071China College of Chemistry Key Laboratory of Advanced Energy Materials Chemistry (Ministry of Education)Renewable Energy Conversion and Storage Center (RECAST)Frontiers Science Center for New Organic MatterNankai UniversityTianjin 300071China

Herein, a site-selective paired electrochemical C–H oxidation of functionalized alkyl arenes promoted by nickel catalyst is disclosed. A Ni(Ⅱ)-dioxygen species formed in situ efficiently enable the oxidation process under mild conditions with a broad substrate scope with excellent functional group compatibilities,such as free carboxylic acid, aldehyde, halogen(including aryl iodide), amide and amino acid. The use of the nickel catalyst in combination with water provides a safe, green and economical method for oxidation of a range of molecules varying in complexity and drug derivatives, demonstrating its potential application in organic synthesis and the pharmaceutical industry. Reaction outcomes and mechanistic studies revealed the key role of the in situ Ni(Ⅱ)-dioxygen species for the subsequent oxidation of C(sp^(3))–H bonds,and short-lived reactive intermediates(aryl radical cation) was rapidly captured by the combination of a bipolar ultramicroelectrode(BUME) with nano-electrospray ionization mass spectrometry.

关键词： Electrochemical C-H oxidation Functionalized alkyl arenes Paired nickel-electrocatalysis H_(2)O oxidation Ketones

Rhodaelectro-Catalyzed C–H and C–C Activation

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CCS Chemistry 2021年第2期3卷 1529-1552页

作者： youai qiu Cuiju Zhu Maximilian Stangier Julia Struwe Lutz Ackermann Institut für Organische und Biomolekulare Chemie Georg-August-Universität GöttingenGöttingen 37077

Rhodium(III)catalysis has set the stage for a plethora of oxidative C–H functionalizations over the last decade,which have predominantly employed stoichiometric amounts of toxic and expensive metal oxidants,such as silver(I)*** the meantime,electrosynthesis has emerged as an increasingly viable alternative for expensive and toxic ***,significant momentum has been achieved with the merger of electrocatalysis with organometallic C–H ***,user-friendly and robust rhodaelectro-catalysis has until very recently proven elusive for oxidative C–H *** minireview highlights the current knowledge and recent advances of electrooxidation in rhodium-catalyzed C–H or C–C activations,with a topical focus on contributions from the Ackermann group through July 2020.

关键词： electrosynthesis rhodium catalysis C–H activation C–C activation mechanistic in-sights rhodaelectro-catalysis

Catalyst-free electrochemical S_(N)Ar of electron-rich fluoroarenes using carboxylic acids

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eScience 2024年第5期4卷 120-131页

作者： Anzai Shi Yaowen Liu Ranran Zhang Zile Zhu youai qiu State Key Laboratory and Institute of Elemento-Organic Chemistry Frontiers Science Center for New Organic MatterCollege of ChemistryNankai University94 Weijin RoadTianjin 300071China

Herein,an electrochemically driven catalyst-free nucleophilic aromatic substitution(S_(N)Ar)of electron-rich fluoroarenes with carboxylic acids as weak nucleophiles under mild conditions was reported.A series of highly valuable ester derivatives were obtained in a direct and rapid *** transformation features commercially available reagents and an exceptionally broad substrate scope with good functional group tolerance,using cheap and abundant electrodes and completed within a short reaction ***-scale synthesis and complex biorelevant compounds ligation further highlighted the potential utility of the *** mechanistic investigations and density functional theory(DFT)calculations verified the feasibility of the proposed pathway of this transformation.

关键词： Electrochemistry DefluorinationElectrochemical S_(N)Ar Catalyst-free process Carboxylic acids

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光电协同催化有机合成研究进展

有机化学 2021年第10期41卷 3935-3947页

作者：杨光王衍伟仇友爱南开大学化学学院元素有机化学国家重点实验室天津300071

随着有机电化学和光化学的复兴,将两者结合的新型光电协同催化有机化学成为了研究热点之一.光电协同催化广泛应用于氧化还原及偶联反应等众多反应体系.本综述总结了近5年来光电催化的最新研究进展,对反应的机理及催化剂进行了系统性的分... 详细信息

随着有机电化学和光化学的复兴,将两者结合的新型光电协同催化有机化学成为了研究热点之一.光电协同催化广泛应用于氧化还原及偶联反应等众多反应体系.本综述总结了近5年来光电催化的最新研究进展,对反应的机理及催化剂进行了系统性的分类,总结了该类反应体系的优势和特点,并且对该研究方向的发展进行了展望.

关键词：有机电化学光化学光电化学协同催化

电化学芳烃C(sp^(2))—H胺化反应的研究进展

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有机化学 2024年第3期44卷 871-891页

作者：朱子乐李鹏飞仇友爱南开大学化学学院元素有机化学国家重点实验室天津300071

苯胺及其衍生物在人类生活和工业生产中被广泛地使用,促使人们探索从相应的C(sp2)—H键直接构建芳香C(sp^(2))—N键的反应方法.近年来,有机电化学作为一种可控、可持续、环境友好和易于扩展规模的方法,受到越来越多的关注,同时也为芳烃... 详细信息

苯胺及其衍生物在人类生活和工业生产中被广泛地使用,促使人们探索从相应的C(sp2)—H键直接构建芳香C(sp^(2))—N键的反应方法.近年来,有机电化学作为一种可控、可持续、环境友好和易于扩展规模的方法,受到越来越多的关注,同时也为芳烃的胺化提供了新的反应模式.在此篇综述中,总结了电化学芳香族C(sp^(2))—H胺化反应中常见的机理途径,根据所涉及的胺源类型对反应实例进行了分类,并对该领域的前景和挑战提供了见解.

关键词：电化学胺化芳烃苯胺 C—H键胺化

Electrocatalytic cleavage of a lignin β-O-4 model compound and coupling with nitrogen-containing aromatics using Prussian blue analogue-derived nickel–cobalt spinel

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Journal of Energy Chemistry 2025年第1期100卷 628-636页

作者： Yi Qi Xueying Chen Bowen Liu Xuliang Lin Xueqing qiu Yanlin Qin Guangdong Provincial Key Laboratory of Plant Resources Biorefinery School of Chemical Engineering and Light Industry Guangdong University of Technology Guangdong Provincial Laboratory of Chemistry and Fine Chemical Engineering Jieyang Center Guangdong Basic Research Center of Excellence for Ecological Security and Green Development Guangdong University of Technology

Electrochemical conversion of lignin for the production of high-value heterocyclic aromatic compounds has great *** demonstrate the targeted synthesis and cation modulation of NiCo2O4spinel nanoboxes,synthesized via cation exchange and calcination *** catalysts exhibit excellent efficacy in the electrocatalytic conversion of lignin model compounds,specifically 2-phenoxy-1-phenylethanol,into nitrogen-containing aromatics,achieving high conversion rates and *** catalysts were synthesized via a cation exchange and calcination oxidation process,using Prussian blue nanocubes as *** porous architecture and polymetallic composition of the NiCo2O4spinel demonstrated superior performance in electrocatalytic oxidative coupling,achieving a 99.2 wt%conversion rate of the 2-phenoxy-1-phenylethanol with selectivities of 37.5 wt%for quinoline derivatives and 31.5 wt%for *** innovations include the development of a sustainable one-pot synthesis method for quinoline derivatives,the elucidation of a multistage reaction pathway involving CAO bond cleavage,hydroxyaldol condensation,and CAN bond formation,and a deeper mechanistic understanding derived from DFT *** work establishes a new strategy for lignin valorization,offering a sustainable route to produce high-value nitrogen-containing aromatics from renewable biomass under mild conditions,without the need for additional reagents.

关键词： Spinel Biomass valorization Electrocatalysis Lignin oxidation Coupling

Potassium and calcium channels in different nerve cells act as therapeutic targets in neurological disorders

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Neural Regeneration Research 2025年第5期20卷 1258-1276页

作者： Qing qiu Mengting Yang Danfeng Gong Haiying Liang Tingting Chen Department of Pharmacology School of PharmacyNantong UniversityNantongJiangsu ProvinceChina Jiangsu Province Key Laboratory of Inflammation and Molecular Drug Target NantongJiangsu ProvinceChina Department of Pharmacy Longyan First Affiliated Hospital of Fujian Medical UniversityLongyanFujian ProvinceChina

The central nervous system, information integration center of the body, is mainly composed of neurons and glial cells. The neuron is one of the most basic and important structural and functional units of the central nervous system, with sensory stimulation and excitation conduction functions. Astrocytes and microglia belong to the glial cell family, which is the main source of cytokines and represents the main defense system of the central nervous system. Nerve cells undergo neurotransmission or gliotransmission, which regulates neuronal activity via the ion channels, receptors, or transporters expressed on nerve cell membranes. Ion channels, composed of large transmembrane proteins, play crucial roles in maintaining nerve cell homeostasis. These channels are also important for control of the membrane potential and in the secretion of neurotransmitters. A variety of cellular functions and life activities, including functional regulation of the central nervous system, the generation and conduction of nerve excitation, the occurrence of receptor potential, heart pulsation, smooth muscle peristalsis, skeletal muscle contraction, and hormone secretion, are closely related to ion channels associated with passive transmembrane transport. Two types of ion channels in the central nervous system, potassium channels and calcium channels, are closely related to various neurological disorders, including Alzheimer's disease, Parkinson's disease, and epilepsy. Accordingly, various drugs that can affect these ion channels have been explored deeply to provide new directions for the treatment of these neurological disorders. In this review, we focus on the functions of potassium and calcium ion channels in different nerve cells and their involvement in neurological disorders such as Parkinson's disease, Alzheimer's disease, depression, epilepsy, autism, and rare disorders. We also describe several clinical drugs that target potassium or calcium channels in nerve cells and could be u

关键词： astrocytes calcium channels central nervous system extracellular ion concentration microglia neurological disorders neurons potassium channels