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学者姓名：林雨琦
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Abstract ：
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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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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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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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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The integration of electrocatalysis with biocatalysis has recently been developed for the stereoselective synthesis of valuable compounds. This integration leverages the high efficiency and exquisite selectivity of enzymes along with the tunability of electrochemical reactions, providing a versatile approach for asymmetric synthesis with broad prospects. In this highlight, recent advances and future development directions in asymmetric synthesis that integrate electrocatalysis with biocatalysis are presented and discussed. We foresee that more valuable stereoselective transformations using this integrated strategy will be developed in the future.
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| GB/T 7714 | Lin, Yuqi , Yu, Jiage , Ye, Ke-Yin . Integrating electrocatalysis with biocatalysis for asymmetric synthesis [J]. | ORGANIC CHEMISTRY FRONTIERS , 2024 , 11 (24) : 7243-7248 . |
| MLA | Lin, Yuqi et al. "Integrating electrocatalysis with biocatalysis for asymmetric synthesis" . | ORGANIC CHEMISTRY FRONTIERS 11 . 24 (2024) : 7243-7248 . |
| APA | Lin, Yuqi , Yu, Jiage , Ye, Ke-Yin . Integrating electrocatalysis with biocatalysis for asymmetric synthesis . | ORGANIC CHEMISTRY FRONTIERS , 2024 , 11 (24) , 7243-7248 . |
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Unlike the well-established fluoroalkylation, the direct incorporation of multiple fluorine atoms into small molecules via iterative fluorinations has been much less investigated. Herein, we report a hypervalent iodine catalytically selective multi-fluorination in which the fluorination degree is controlled by the delicate balance between the HF/amine ratios. The pros and cons of hypervalent iodine catalysis and the previously established electrochemical approach in the iterative multi-fluorinations are also provided.
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| GB/T 7714 | Ding, Cheng-Lin , Li, Hechen , Zhong, Yi et al. Hypervalent iodine catalysis enabled iterative multi-fluorination: not just a simple alternative for the electrochemical approach [J]. | CHEMICAL COMMUNICATIONS , 2024 , 60 (93) : 13738-13741 . |
| MLA | Ding, Cheng-Lin et al. "Hypervalent iodine catalysis enabled iterative multi-fluorination: not just a simple alternative for the electrochemical approach" . | CHEMICAL COMMUNICATIONS 60 . 93 (2024) : 13738-13741 . |
| APA | Ding, Cheng-Lin , Li, Hechen , Zhong, Yi , Lin, Yuqi , Ye, Ke-Yin . Hypervalent iodine catalysis enabled iterative multi-fluorination: not just a simple alternative for the electrochemical approach . | CHEMICAL COMMUNICATIONS , 2024 , 60 (93) , 13738-13741 . |
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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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An electrochemical gem-difluorination of indeno[1,2-c]furans using commercially available and easy-to-use triethylamine trihydrofluoride as both the electrolyte and fluorinating agent was developed. Remarkably, different reaction pathways of indeno[1,2-c]furans, i.e., paired electrolysis and net oxidation, are operative in a batch reactor and a continuous-flow microreactor to afford the corresponding gem-difluorinated indanones and indenones, respectively.
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| GB/T 7714 | Yuan, Guo-Cai , Gao, Fang-Ling , Liu, Kang-Wei et al. Batch and Continuous-Flow Electrochemical Geminal Difluorination of Indeno[1,2-c]furans [J]. | ORGANIC LETTERS , 2024 , 26 (28) : 6059-6064 . |
| MLA | Yuan, Guo-Cai et al. "Batch and Continuous-Flow Electrochemical Geminal Difluorination of Indeno[1,2-c]furans" . | ORGANIC LETTERS 26 . 28 (2024) : 6059-6064 . |
| APA | Yuan, Guo-Cai , Gao, Fang-Ling , Liu, Kang-Wei , Li, Minggang , Lin, Yuqi , Ye, Ke-Yin . Batch and Continuous-Flow Electrochemical Geminal Difluorination of Indeno[1,2-c]furans . | ORGANIC LETTERS , 2024 , 26 (28) , 6059-6064 . |
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The invention of novel linkers is a long-lasting task in the area of the sulfur(VI) fluoride exchange reaction (SuFEx). Compared with the most frequently investigated sulfonyl fluorides, synthetic accessibility toward its mono-aza isostere, i.e., sulfonimidoyl fluorides is still limited. Herein, we report an electrochemical carbonfluorination of the readily available N-sulfinylamines to access various aryl and alkyl sulfonimidoyl fluorides. The transformation is characterized by the ready availability of starting materials, mild reaction conditions, and obviating metal catalysts and chemical oxidants.
Keyword ：
Electrochemical Electrochemical Green chemistry Green chemistry N-Sulfinylamines N-Sulfinylamines Sulfonimidoyl fluorides Sulfonimidoyl fluorides Sulfur(VI) fluoride exchange reaction Sulfur(VI) fluoride exchange reaction
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| GB/T 7714 | Gao, Fang-Ling , He, Xinglei , Zhao, Bin et al. Electrochemical Conversion of N-Sulfinylamines to Sulfonimidoyl Fluorides [J]. | CHINESE JOURNAL OF CHEMISTRY , 2024 , 43 (7) : 769-774 . |
| MLA | Gao, Fang-Ling et al. "Electrochemical Conversion of N-Sulfinylamines to Sulfonimidoyl Fluorides" . | CHINESE JOURNAL OF CHEMISTRY 43 . 7 (2024) : 769-774 . |
| APA | Gao, Fang-Ling , He, Xinglei , Zhao, Bin , Lin, Yuqi , Ye, Ke-Yin . Electrochemical Conversion of N-Sulfinylamines to Sulfonimidoyl Fluorides . | CHINESE JOURNAL OF CHEMISTRY , 2024 , 43 (7) , 769-774 . |
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