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CN: 11-1818/O6
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Organic Electrochemistry and Its Integration into Chemistry Teaching
Hong Yan, Wenfeng Wang, Keyin Ye, Yaofeng Yuan
University Chemistry 2025, 40 (
5
): 301 -310. DOI:
10.12461/PKU.DXHX202407027
Abstract
(
3954
)
Full text @ ScienceDirect
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Organic electrochemistry has been recognized as one of the top ten emerging technologies in chemistry by International Union of Pure and Applied Chemistry (IUPAC) in 2023. As a crucial branch of fundamental chemistry in undergraduate education, electrochemistry is primarily addressed in the context of inorganic chemistry (specifically redox reactions) and physical chemistry (in relation to electrolyte solutions). However, references to organic electrochemistry in undergraduate curricula are notably scarce. This article presents recent research trends in organic electrochemistry and discusses considerations for incorporating organic electrochemistry into undergraduate chemistry teaching.
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Electrochemical Synthesis of 2,5-Diphenyl-1,3,4-Oxadiazole: A Recommended Comprehensive Organic Chemistry Experiment
Shuhui Li, Rongxiuyuan Huang, Yingming Pan
University Chemistry 2025, 40 (
5
): 357 -365. DOI:
10.12461/PKU.DXHX202407028
Abstract
(
4665
)
Full text @ ScienceDirect
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This experiment employs an electrochemical synthesis method to produce 2,5-diphenyl-1,3,4-oxadiazole from benzoylhydrazine. The structure of the synthesized product is identified and characterized using analytical techniques, including NMR, infrared spectroscopy, and melting point determination. In comparison to traditional organic synthesis methods, the electrochemical approach aligns with green chemistry principles, offering advantages such as simplicity, mild reaction conditions, and high yield. This experiment encourages students, who have mastered fundamental organic laboratory techniques, to explore cutting-edge electrochemical synthesis methods and gain insights into the application of electrochemistry in organic synthesis. Additionally, it fosters students’ interest in scientific research and innovative thinking, thereby enriching the content of basic organic chemistry education.
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Electrochemical Transformation of Organosulfur Compounds
Yongjian Zhang, Fangling Gao, Hong Yan, Keyin Ye
University Chemistry 2025, 40 (
5
): 311 -317. DOI:
10.12461/PKU.DXHX202407035
Abstract
(
5236
)
Full text @ ScienceDirect
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The synthesis and transformation of organosulfur compounds hold significant theoretical and practical value. However, the coverage of organosulfur compounds in fundamental organic chemistry textbooks is limited. This article begins with a brief overview of the key concepts related to organosulfur compounds as presented in the basic organic chemistry course. It then compares and discusses recent advancements in the electrochemical transformations of these compounds. This study aims to enhance the understanding of chemistry major students regarding the cutting-edge developments in organic electrochemistry as it pertains to organosulfur chemistry.
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Application of Electrochemical Synthesis in the Teaching of Organic Chemistry
Renxiu Zhang, Xin Zhao, Yunfei Zhang
University Chemistry 2025, 40 (
4
): 174 -180. DOI:
10.12461/PKU.DXHX202406116
Abstract
(
3814
)
Full text @ ScienceDirect
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Electrochemistry is extensively studied and applied in analytical and physical chemistry; however, its integration into organic chemistry remains limited. This article aims to promote the incorporation of electrochemical techniques in both theoretical and experimental organic chemistry education. We seek to instill a “green chemistry” ethos among students and to elucidate the significance of organic electrochemical synthesis technologies in advancing ecological sustainability, addressing national needs, and safeguarding public health. This approach is intended to enhance students’ professional identity and social responsibility. By implementing electrochemical applications in organic chemistry and providing guidance for their educational use, we aim to improve the quality of organic chemistry instruction and foster the deeper development of research in this field.
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Recent Advances in
In-Situ
Raman Spectroscopy for Investigating Electrocatalytic Organic Reaction Mechanisms
Jiajie Li, Xiaocong Ma, Jufang Zheng, Qiang Wan, Xiaoshun Zhou, Yahao Wang
University Chemistry 2025, 40 (
4
): 261 -276. DOI:
10.12461/PKU.DXHX202406117
Abstract
(
5613
)
Full text @ ScienceDirect
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In recent years, electrocatalytic organic synthesis has attracted increasing attention. Its advantages such as low pollution and high atomic efficiency give it a huge advantage over traditional organic synthesis methods and meet the social requirements of green chemistry. Therefore, detecting the reaction process and key intermediates at the electrode interface from the molecular level has important guiding significance for understanding the reaction mechanism and designing more efficient catalysts. Raman spectroscopy is a type of vibrational spectroscopy that is non-destructive and uninterrupted by water. In particular, surface-enhanced Raman spectroscopy has ultra-high surface sensitivity. It can provide key information on the catalyst surface structure, adsorbed substances and intermediates during the reaction, and provide a reliable platform for exploring the reaction mechanism. This article reviews the recent advances in electrocatalytic organic reaction mechanisms probed by
in-situ
Raman spectroscopy. Specifically, Raman spectroscopy reveals important intermediates, active substances and reaction pathways in electrocatalytic hydrogenation, activations of C―O, C―X (X = F, Cl, Br, I) and C―H bonds. By analyzing specific cases, it aims to help students understand the research frontiers of organic electrosynthesis and stimulate interest in exploring synthetic electrochemistry, one of IUPAC’s “Top Ten Emerging Technologies in Chemistry” in 2023.
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Innovative Experiment of Electrochemical Dearomative Spirocyclization of
N
-Acyl Sulfonamides
Caixia Lin, Ting Liu, Zhaojiang Shi, Hong Yan, Keyin Ye, Yaofeng Yuan
University Chemistry 2025, 40 (
4
): 359 -366. DOI:
10.12461/PKU.DXHX202406107
Abstract
(
4380
)
Full text @ ScienceDirect
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Spiro compounds are of great interest in drug design and organic synthesis due to their unique three-dimensional structures and biological activities. Traditional methods for synthesizing spiro compounds often involve the use of stoichiometric oxidants, which can be harsh and complicated. In this experiment, dearomative spirocyclization of N-acyl sulfonamides is achieved efficiently and in an environmentally friendly manner through electrochemical oxidation. During the experimental course, students will learn the fundamental principles of electrochemical synthesis, acquire operational skills, and gain an understanding of the synthetic mechanisms involved in electrochemical dearomative spirocyclization. By guiding students to explore the experimental mechanisms and integrating theoretical knowledge with practical application, this approach enhances their experimental skills and scientific inquiry abilities while fostering an appreciation for green chemistry and sustainable synthesis methods.
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Electrochemically Driven Denitrative Borylation and Fluorosulfonylation of Nitroarenes
Zhongyan Cao, Youzhi Xu, Menghua Li, Xiao Xiao, Xianqiang Kong, Deyun Qian
University Chemistry 2025, 40 (
4
): 277 -281. DOI:
10.12461/PKU.DXHX202407017
Abstract
(
2396
)
Full text @ ScienceDirect
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Nitroarenes are widely utilized in organic synthesis and are a key topic in undergraduate organic chemistry curricula. However, efficient methods for denitrative transformations of nitroarenes under mild conditions remain limited. In recent years, green electrochemical synthesis has emerged as a promising approach for the selective C―N bond transformations of nitroarenes. This mini-review highlights recent advances in electrochemically facilitated denitrative transformations of nitroarenes, using reaction examples that are accessible to undergraduate students. These examples aim to expand students’ understanding of denitrative processes, stimulate their interest in the field, enhance their learning experience, and enrich their knowledge base.
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Advances in the Application of Electrochemical Regulation in Investigating the Electron Transport Properties of Single-Molecule Junctions
Jingwen Wang, Minghao Wu, Xing Zuo, Yaofeng Yuan, Yahao Wang, Xiaoshun Zhou, Jianfeng Yan
University Chemistry 2025, 40 (
3
): 291 -301. DOI:
10.12461/PKU.DXHX202406023
Abstract
(
3821
)
Full text @ ScienceDirect
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Single-molecule electronics, a pivotal branch of nanotechnology, focuses on the electrical properties of individual molecules, providing a theoretical foundation and technical support for the development of ultra-compact, energy-efficient electronic devices. Achieving precise control over electron transport in single-molecule junctions poses a significant technical challenge in this field. Electrochemical regulation, characterized by its exceptional tunability and reversibility, has emerged as a promising area of research within single-molecule electronics. This review highlights the progress made in the application of electrochemical control strategies over the past decade, encompassing the modulation of electron transport energy levels, molecular valence states, bonding mechanisms between electrodes and molecules, as well as the control of ionic liquid double-layer gating. By analyzing specific case studies, the aim is to enhance students’ understanding of the forefront of single-molecule electronics and its critical importance in contemporary nanoelectronics.
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Exploring the Role of Electrochemical Technologies in Everyday Life
Shuhui Li, Xucen Wang, Yingming Pan
University Chemistry 2025, 40 (
3
): 302 -307. DOI:
10.12461/PKU.DXHX202406059
Abstract
(
3597
)
Full text @ ScienceDirect
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In recent years, electrochemical technology has not only advanced progress in energy, environmental protection, and materials science but also enhanced the convenience and security of our daily lives. To bridge the gap between electrochemistry and real-world applications and to elucidate the underlying principles behind observable phenomena, this article introduces key electrochemical concepts in areas such as self-heating packs, the sports industry, and nucleic acid detection. The focus will be on electrochemical corrosion heating, electrochemical energy storage technologies, and the use of graphene nanocomposites in nucleic acid sensors. This paper aims to enhance public understanding of electrochemistry, thereby fostering a deeper comprehension of everyday phenomena and improving scientific literacy.
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Application of Electrochemical Techniques in Supramolecular Chemistry
Cen Zhou, Biqiong Hong, Yiting Chen
University Chemistry 2025, 40 (
3
): 308 -317. DOI:
10.12461/PKU.DXHX202406086
Abstract
(
3407
)
Full text @ ScienceDirect
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The most frequently used scaffolds in supramolecular chemistry are typically redox active and susceptible to electron transfer. As a basic tool, electrochemical techniques assist in the generation of active species, which leads to altered interactions between molecules. Meanwhile, more information on energy and kinetics that is not available with other characterization techniques can be provided. In this review, the typically examples on applying electrochemical techniques in supramolecular chemistry are briefly summarized.
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Electrochemical Modifications of Native Peptides
Zihan Lin, Wanzhen Lin, Fa-Jie Chen
University Chemistry 2025, 40 (
3
): 318 -327. DOI:
10.12461/PKU.DXHX202406089
Abstract
(
3462
)
Full text @ ScienceDirect
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The rapid development of peptide therapeutics has sparked interest in the chemical modification of native peptides. Electrochemical modification has emerged as a promising technique, offering distinct advantages over traditional chemical approaches, including mild reaction conditions, high chemo-selectivity, and high atom efficiency, all of which align with the principles of green chemistry. This approach has found widespread applications in organic synthesis, with significant progress observed in recent years regarding its use in the modification of native peptides. In this review, we introduce the latest advancements in the field of electrochemical modifications of native peptides, focusing on experimental protocols, reaction mechanisms and synthetic applications.
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Electrochemistry Mediated Direct Amination to Construct the Hemiaminal Ether Skeletons (HESs)
Ke Liu, Mingjing Deng, Jingbo Chang, Ailing Wang, Guoshuai Wu, Longyang Dian
University Chemistry 2025, 40 (
2
): 272 -277. DOI:
10.12461/PKU.DXHX202405060
Abstract
(
3910
)
Full text @ ScienceDirect
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This paper presents a novel electrochemical synthesis experiment designed for undergraduate education, utilizing inexpensive and readily available benzotriazole and tetrahydrofuran as starting materials. The experiment successfully achieves the direct amination of ether-derived carbon-hydrogen (C(
sp
3
)―H) bonds at room temperature to construct hemiaminal ether skeletons (HESs). By integrating scientific research outcomes with innovative pedagogical approaches, this experiment aims to stimulate and cultivate students’ creative thinking while providing insights into the latest trends in modern green organic electrochemical synthesis.
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Electrochemical Reduction of Benzothiophene Derivatives
Shijie Bo, Weisi Guo, Shuwen Wang, Ran Song, Ming Li, Linbao Zhang
University Chemistry 2025, 40 (
1
): 303 -308. DOI:
10.12461/PKU.DXHX202404111
Abstract
(
2260
)
Full text @ ScienceDirect
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Organic electrosynthesis is a green, mild, and efficient synthesis method, but it has not been effectively promoted in undergraduate organic experimental teaching. Dihydrobenzothiophene derivatives are widely found in biologically active compounds and have important application value in the pharmaceutical industry. Hydrogenation reduction of benzothiophene derivatives is the simplest and most direct method to obtain such compounds, but traditional reduction methods have many shortcomings. We developed an electrochemical-promoted reduction method of benzothiophene derivatives using electrons as the reducing agent and hexafluoroisopropanol as the hydrogen donor. On this basis, an organic chemistry experiment was designed to prepare 2,3-dihydrobenzo[
b
]thiophene 1,1-dioxide by electrochemical reduction of benzothiophene sulfone.
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Recent Advances in the Electrochemical Aziridination of Alkenes
Hong He, Xiadie Wu, Zhongwei Hou, Lei Wang
University Chemistry 2025, 40 (
1
): 196 -205. DOI:
10.12461/PKU.DXHX202404145
Abstract
(
2803
)
Full text @ ScienceDirect
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Aziridines are significant organic structural motifs that serve as key intermediates for the synthesis of diverse nitrogen-containing compounds. Organic electrochemistry has emerged as an environmentally friendly and sustainable approach to organic synthesis, facilitating a range of chemical transformations without the need for external redox reagents. This review highlights recent advancements in the electrochemical aziridination of alkenes for the synthesis of aziridines, with a focus on reaction design, active intermediates, and future prospects for development.
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Novel Experimental Development: Preparation, Characterization, and Application of Tungsten Trioxide Photoanodes in the Halogenation of Benzyl Ethers
Ruitao Liu, Benhong Pan, Nenghui Pan, Liang Xu, Zhenhua Li
University Chemistry 2025, 40 (
1
): 309 -317. DOI:
10.12461/PKU.DXHX202404106
Abstract
(
3086
)
Full text @ ScienceDirect
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Photoelectrochemical (PEC) technology is regarded as an environmentally benign route for H
2
production via water splitting. Among them, directly PEC splitting of seawater is expected to significantly reduce the cost of H
2
production, which has attracted wide attention. However, the reaction efficiency is always hindered by the energetically and kinetically demanding O
2
evolution reaction. This experimental design a PEC strategy for anisole halogenation with simulated seawater over an WO
3
photoanode, producing high value-added organic halides coupled with cathodic H
2
production. This experiment introduces scientific research achievements into teaching, guiding students to understand the development of cutting-edge fields in the discipline, helping to cultivate their scientific thinking ability, and stimulating their interest in scientific research.
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Comprehensive Experimental Design for Solvent-Controlled Electrochemical Synthesis of Selenium-Containing Pyranone and Chalcone
Balati Hasimujiang, Caifeng Hu, Yawen Huang, Mu Chen, Xinwei Hu, Zhixiong Ruan
University Chemistry 2024, 39 (
12
): 273 -283. DOI:
10.12461/PKU.DXHX202404040
Abstract
(
2675
)
Full text @ ScienceDirect
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Electrochemical organic synthesis is an environmentally friendly, mild, and efficient methodology that has gained widespread acceptance in oxidation, reduction, and redox reaction systems, showcasing significant potential. This experiment focused on the synthesis of selenium-containing pyranones and chalcones using 1-(2-methoxyphenyl)-3-phenylpropyl-2-oxo-1-one and diphenyl diselenide (PhSeSePh) as starting materials, employing a solvent controlled electrochemical strategy to construct C―Se bonds and explore innovative electrochemical synthesis methods for selenium-containing compounds. Drawing on the research achievements of our group, we have designed a comprehensive experiment for the solvent-regulated electrochemical synthesis of these compounds. The experimental framework involves various operational steps, such as substrate preparation, electrochemical synthesis analysis, cyclic voltammetry studies, structural characterization of target products, and crystal cultivation. This hands-on approach enhances students’ practical skills in experimental techniques, silica gel column chromatography separation and purification, and structural analysis. Our experimental design emphasizes green organic synthesis, integrating interdisciplinary knowledge from both organic chemistry and electrochemistry to develop novel synthetic methods for selenium-containing heterocyclic compounds.
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Overview of Organic Electrochemical Synthesis
Shuhui Li, Yujing Zhou, Haitao Tang
University Chemistry 2025, 40 (
2
): 210 -215. DOI:
10.12461/PKU.DXHX202405077
Abstract
(
5447
)
Full text @ ScienceDirect
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Organic electrochemical synthesis stands out for its environmentally friendly and efficient characteristics. In recent years, the field has seen rapid advancements in both research and industrial applications, making it a prominent area of study. Therefore, understanding the fundamental concepts of organic electrochemical synthesis is of significant importance. This paper provides an overview of the basic principles, advantages, electrochemical synthesis apparatus, electrolytic methods, and recent developments in the field. The goal is to equip students with the foundational knowledge of organic electrochemical synthesis, highlight its benefits and cutting-edge progress, foster an awareness of green chemistry, and broaden their overall understanding of chemistry.
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Electrochemical Oxidation of Sulfides to Sulfoxides
Linbao Zhang, Weisi Guo, Shuwen Wang, Ran Song, Ming Li
University Chemistry 2024, 39 (
11
): 204 -209. DOI:
10.3866/PKU.DXHX202401009
Abstract
(
2721
)
Full text @ ScienceDirect
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Electrochemical synthesis is a green, efficient, and sustainable organic synthesis scheme, but its application in undergraduate basic experiments has not been effectively promoted. Sulfoxide compounds are commonly found in functional organic compounds and are also widely used in natural drugs or materials. The research on the synthesis methods of sulfoxide compounds has always been a hot topic in the field of organic synthesis, but traditional methods have many shortcomings. We have developed an electrochemical scheme for selectively oxidizing sulfides to sulfoxides, where sodium chloride plays a dual role: (1) as an electrolyte; (2) as a redox mediator.
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