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学者姓名:叶克印
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Abstract :
Efficient control over several possible reaction pathways of free radicals is the chemical basis of their highly selective transformations. Among various competing reaction pathways, sulfonimidyl radicals generated from the electrolysis of 2-alkynylbenzenesulfonamides undergo cascade migratory or ortho-cyclization cyclization selectively. It is found that the incorporation of an extra 2-methyl substituent biases the selective migration of the acyl- over vinyl-linker of the key spirocyclic cation intermediate and thus serves as an enabling handle to achieve the synthetically interesting yet under-investigated cascade migratory cyclization of spirocyclic cations.
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GB/T 7714 | Shi, Zhaojiang , Dong, Shicheng , Liu, Ting et al. Electrochemical cascade migratory versus ortho-cyclization of 2-alkynylbenzenesulfonamides [J]. | CHEMICAL SCIENCE , 2024 , 15 (8) : 2827-2832 . |
MLA | Shi, Zhaojiang et al. "Electrochemical cascade migratory versus ortho-cyclization of 2-alkynylbenzenesulfonamides" . | CHEMICAL SCIENCE 15 . 8 (2024) : 2827-2832 . |
APA | Shi, Zhaojiang , Dong, Shicheng , Liu, Ting , Wang, Wei-Zhen , Li, Nan , Yuan, Yaofeng et al. Electrochemical cascade migratory versus ortho-cyclization of 2-alkynylbenzenesulfonamides . | CHEMICAL SCIENCE , 2024 , 15 (8) , 2827-2832 . |
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The development of efficient and sustainable methods to obtain spirocyclic compounds is of significance as these structures are widely found in pharmaceuticals and agrochemicals. Herein, we disclose an electrochemical dearomative spirocyclization of N-acyl sulfonamides in a continuous-flow cell. The reaction is simple and efficient without external catalysts or supporting electrolytes and could be applied in a decagram-scale synthesis.
Keyword :
Continuous-flow Continuous-flow Cyclization Cyclization Dearomatization Dearomatization Electrochemistry Electrochemistry Methodology and reactions Methodology and reactions Spirocyclization Spirocyclization Sulfonamides Sulfonamides
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GB/T 7714 | Liu, Ting , Shi, Zhaojiang , Yuan, Yaofeng et al. Electrochemical Dearomative Spirocyclization of N-Acyl Sulfonamides in a Continuous-Flow Cell [J]. | CHINESE JOURNAL OF CHEMISTRY , 2024 , 42 (9) : 980-984 . |
MLA | Liu, Ting et al. "Electrochemical Dearomative Spirocyclization of N-Acyl Sulfonamides in a Continuous-Flow Cell" . | CHINESE JOURNAL OF CHEMISTRY 42 . 9 (2024) : 980-984 . |
APA | Liu, Ting , Shi, Zhaojiang , Yuan, Yaofeng , Lin, Yuqi , Ye, Ke-Yin . Electrochemical Dearomative Spirocyclization of N-Acyl Sulfonamides in a Continuous-Flow Cell . | CHINESE JOURNAL OF CHEMISTRY , 2024 , 42 (9) , 980-984 . |
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Abstract :
有机电化学合成技术以电子代替传统有机反应的氧化还原剂,具有经济高效、环境友好、可持续发展等特点。通过将电化学合成苯并噁噻嗪二氧化物的科研成果转化为本科生实验,可以让学生建立“绿色化学”的理念,了解有机电化学合成技术对服务人类生态文明、国家需求和维护人民生命健康的重要意义,从而提高学生的专业认同感和社会责任感。通过将课程思政渗透到实验教学的全过程,全方位培养学生的科学思维、科学能力和科学素养。
Keyword :
实验教学 实验教学 电化学合成 电化学合成 课程思政 课程思政
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GB/T 7714 | 林彩霞 , 施兆江 , 余意 et al. 电化学合成苯并噁噻嗪二氧化物实验的课程思政设计 [J]. | 大学化学 , 2024 , 39 (02) : 61-66 . |
MLA | 林彩霞 et al. "电化学合成苯并噁噻嗪二氧化物实验的课程思政设计" . | 大学化学 39 . 02 (2024) : 61-66 . |
APA | 林彩霞 , 施兆江 , 余意 , 鄢剑锋 , 叶克印 , 袁耀锋 . 电化学合成苯并噁噻嗪二氧化物实验的课程思政设计 . | 大学化学 , 2024 , 39 (02) , 61-66 . |
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The preparation of polycyclic aromatic hydrocarbons (PAHs) by the Scholl reaction is typically performed by using superstoichiometric oxidants. Herein, we develop an electrochemical continuous-flow Scholl reaction to access PAHs that features a reduction in the use of supporting electrolytes and easy scale-up without changing the reaction conditions and setups. This reaction allows the synthesis of distorted PAHs containing three [5]helicene units that possess intriguing electronic and optical properties.
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GB/T 7714 | Wang, Wei-Zhen , Wang, Qiang , He, Xinglei et al. Electrochemical Continuous-Flow Scholl Reaction toward Polycyclic Aromatic Hydrocarbons [J]. | ORGANIC LETTERS , 2024 , 26 (11) : 2243-2248 . |
MLA | Wang, Wei-Zhen et al. "Electrochemical Continuous-Flow Scholl Reaction toward Polycyclic Aromatic Hydrocarbons" . | ORGANIC LETTERS 26 . 11 (2024) : 2243-2248 . |
APA | Wang, Wei-Zhen , Wang, Qiang , He, Xinglei , Shen, Yi-Han , Zhai, Zi'ang , Zhang, Ruiying et al. Electrochemical Continuous-Flow Scholl Reaction toward Polycyclic Aromatic Hydrocarbons . | ORGANIC LETTERS , 2024 , 26 (11) , 2243-2248 . |
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An electrochemical intramolecular 5-exo-dig aza-cyclization of 2-alkynylbenzamides and subsequent nucleophilic fluorination have been developed to afford the highly selective synthesis of mono- and trifluorinated isoindolin-1-one derivatives. This work demonstrates the unique capability of synthetic electrochemistry in controlling reaction selectivity through the applied electrolytic parameters. In addition, the obtained monofluorinated 3-methyleneisoindolin-1-one (19) displays interesting photophysical properties that are not observed in its nonfluorinated analog.
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GB/T 7714 | Ding, Cheng-Lin , Xu, Qiaohong , Wu, Shuai et al. Current-Controlled Electrochemical Approach Toward Mono- and Trifluorinated Isoindolin-1-one Derivatives [J]. | ORGANIC LETTERS , 2024 , 26 (8) : 1645-1651 . |
MLA | Ding, Cheng-Lin et al. "Current-Controlled Electrochemical Approach Toward Mono- and Trifluorinated Isoindolin-1-one Derivatives" . | ORGANIC LETTERS 26 . 8 (2024) : 1645-1651 . |
APA | Ding, Cheng-Lin , Xu, Qiaohong , Wu, Shuai , Zhong, Yi , He, Xinglei , Lin, Yuqi et al. Current-Controlled Electrochemical Approach Toward Mono- and Trifluorinated Isoindolin-1-one Derivatives . | ORGANIC LETTERS , 2024 , 26 (8) , 1645-1651 . |
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We herein report a cobalt-catalyzed intramolecular oxytrifluoromethylation of N-allylamides for the efficient synthesis of trifluoromethyl-containing oxazolines with Togni's reagent II as the trifluoromethyl precursor. The protocol features mild reaction conditions and good functional group compatibility. Preliminary mechanistic investigations suggest the involvement of free radicals in this transformation.
Keyword :
cobalt catalysis cobalt catalysis N-allylamides N-allylamides oxazolines oxazolines oxytrifluoromethylation oxytrifluoromethylation Togni's reagent II Togni's reagent II
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GB/T 7714 | Han, Jun-Fa , Gao, Fang-Ling , Chen, Lin et al. Cobalt-Catalyzed Oxytrifluoromethylation of N-Allylamides toward Trifluoromethyl-Containing Oxazolines [J]. | ASIAN JOURNAL OF ORGANIC CHEMISTRY , 2024 , 13 (3) . |
MLA | Han, Jun-Fa et al. "Cobalt-Catalyzed Oxytrifluoromethylation of N-Allylamides toward Trifluoromethyl-Containing Oxazolines" . | ASIAN JOURNAL OF ORGANIC CHEMISTRY 13 . 3 (2024) . |
APA | Han, Jun-Fa , Gao, Fang-Ling , Chen, Lin , He, Zi-Xin , Lin, Yuqi , Ye, Ke-Yin . Cobalt-Catalyzed Oxytrifluoromethylation of N-Allylamides toward Trifluoromethyl-Containing Oxazolines . | ASIAN JOURNAL OF ORGANIC CHEMISTRY , 2024 , 13 (3) . |
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Sulfonimidoyl fluorides, the aza-bioisostere of sulfonyl fluorides, are emerging as a promising link -age agent in the sulfur(VI) fluoride exchange reaction (SuFEx). However, conventional synthetic approaches typically require the use of either unstable sulfonimidoyl chlorides, toxic and corrosive sulfur fluorides, or expensive electrophilic fluorinating agents. Herein, we report an electrochemistry-en-abled oxidative nucleophilic fluorination of readily available and bench-stable sulfinamides using a com-mercially available and easy-to-handle triethylamine trihydrofluoride. With other nucleophilic agents, this electrochemical approach also serves as a general approach to diverse sulfonimidoyl derivatives, including sulfonimidoyl azides and acetates.
Keyword :
click chemistry click chemistry electrochemistry electrochemistry sulfinamide sulfinamide sulfonimidoyl fluoride sulfonimidoyl fluoride sulfur (VI) fluoride exchange reaction sulfur (VI) fluoride exchange reaction
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GB/T 7714 | Jiang, Yi-Min , Lin, Yong-Ying , Zhu, Lingyun et al. A General Electrochemical Synthesis of Sulfonimidoyl Fluorides, Azides, and Acetates [J]. | CCS CHEMISTRY , 2024 , 6 (8) : 2021-2030 . |
MLA | Jiang, Yi-Min et al. "A General Electrochemical Synthesis of Sulfonimidoyl Fluorides, Azides, and Acetates" . | CCS CHEMISTRY 6 . 8 (2024) : 2021-2030 . |
APA | Jiang, Yi-Min , Lin, Yong-Ying , Zhu, Lingyun , Yu, Yi , Li, Yuanming , Lin, Yuqi et al. A General Electrochemical Synthesis of Sulfonimidoyl Fluorides, Azides, and Acetates . | CCS CHEMISTRY , 2024 , 6 (8) , 2021-2030 . |
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Porous materials are emerging recyclable electrocatalysts that exhibit many advantages such as rich pore environments, tunable structures and functionalities, and large specific surface areas. However, the research of these materials in organic electrocatalysis is promising but only emerged recently. In this review, we summarized the latest research progress of porous carbon materials, metal-organic frameworks (MOFs), and covalent-organic frameworks (COFs) in organic electrocatalysis, focusing on their structural optimization, electrochemical performance, and reaction mechanisms. In addition, the main challenges and future directions in this field were also discussed. We hope that this review can inspire more research interest of synthetic organic chemists in the development of porous electrocatalysts in organic electrocatalysis.
Keyword :
Electrocatalysis Electrocatalysis Heterogeneous catalysis Heterogeneous catalysis Organic synthesis Organic synthesis Porous electrocatalysts Porous electrocatalysts
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GB/T 7714 | He, Xinglei , Yan, Hong , Ye, Ke-Yin . Porous electrocatalysts modified electrodes in organic electrocatalysis [J]. | CURRENT OPINION IN ELECTROCHEMISTRY , 2024 , 45 . |
MLA | He, Xinglei et al. "Porous electrocatalysts modified electrodes in organic electrocatalysis" . | CURRENT OPINION IN ELECTROCHEMISTRY 45 (2024) . |
APA | He, Xinglei , Yan, Hong , Ye, Ke-Yin . Porous electrocatalysts modified electrodes in organic electrocatalysis . | CURRENT OPINION IN ELECTROCHEMISTRY , 2024 , 45 . |
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Diamines play important roles in synthetic organic chemistry and thus facilitate life and materials sciences. Herein we report a cobalt-catalyzed ring opening, nucleophilic amination of aziridines and azetidines with N-fluorosulfonamides toward a wide range of 1,2- and 1,3-diamine derivatives in moderate to good yields under mild conditions. A cobalt-catalyzed ring opening, nucleophilic amination of aziridines and azetidines with N-fluorosulfonamides has been established toward a wide range of 1,2- and 1,3-diamine derivatives in moderate to good yields under mild conditions.
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GB/T 7714 | Cheng, Ling-Chao , Wang, Zhihua , He, Xinglei et al. Cobalt-catalyzed amination of aziridines and azetidines toward 1,2-and 1,3-diamines [J]. | ORGANIC & BIOMOLECULAR CHEMISTRY , 2024 , 22 (13) : 2554-2557 . |
MLA | Cheng, Ling-Chao et al. "Cobalt-catalyzed amination of aziridines and azetidines toward 1,2-and 1,3-diamines" . | ORGANIC & BIOMOLECULAR CHEMISTRY 22 . 13 (2024) : 2554-2557 . |
APA | Cheng, Ling-Chao , Wang, Zhihua , He, Xinglei , Liang, Wangfu , Ye, Ke-Yin . Cobalt-catalyzed amination of aziridines and azetidines toward 1,2-and 1,3-diamines . | ORGANIC & BIOMOLECULAR CHEMISTRY , 2024 , 22 (13) , 2554-2557 . |
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Organofluorine compounds find extensive application in the fields of agrochemicals, pharmaceuticals, materials science, and molecular imaging. Introducing fluorine atoms can provide organic compounds with unique physicochemical properties or improve their biological activity. Although significant progress has been made in the chemical synthesis of fluorine-containing compounds, achieving selective fluorination under mild conditions remains extremely challenging. Introducing biocatalytic approaches in organofluorine chemistry is an important strategy given their high efficiency, selectivity, and environmental friendliness. In this review, we present the discovery of fluorinated natural products and fluorinases, the crystal structure and the directed evolution of fluorinases, with a focus on recent advances in the enzymatic synthesis of fluorine-containing compounds in recent years. It is hoped that this review will help to promote the field of biocatalytic organofluorine compound synthesis. Organofluorine compounds play a crucial role in agrochemicals, pharmaceuticals, and materials science. Biocatalysis has emerged as an essential strategy in the synthesis of fluorinated molecules under mild conditions. This review mainly focused on recent advances in the enzymatic synthesis of fluorine-containing compounds. Furthermore, the identification of fluorinated natural products and fluorinases, the crystal structure and the directed evolution of fluorinases were discussed. image
Keyword :
C-F bond C-F bond enzyme enzyme fluorinase fluorinase fluorinated compounds fluorinated compounds fluorination fluorination
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GB/T 7714 | Lin, Yuqi , Xue, Wanqing , Li, Hechen et al. Advances in Enzymatic Incorporation of Small Fluorine Modules [J]. | EUROPEAN JOURNAL OF ORGANIC CHEMISTRY , 2024 , 27 (17) . |
MLA | Lin, Yuqi et al. "Advances in Enzymatic Incorporation of Small Fluorine Modules" . | EUROPEAN JOURNAL OF ORGANIC CHEMISTRY 27 . 17 (2024) . |
APA | Lin, Yuqi , Xue, Wanqing , Li, Hechen , Su, Bingmei , Lin, Juan , Ye, Ke-Yin . Advances in Enzymatic Incorporation of Small Fluorine Modules . | EUROPEAN JOURNAL OF ORGANIC CHEMISTRY , 2024 , 27 (17) . |
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