The strategic incorporation of the pharmacologically privileged trifluoroethyl group into the biologically significant benzofuran scaffold offers considerable potential for medicinal and agrochemical applications. Herein, an atom‐economical synthetic approach to 3‐trifluoroethyl benzofurans through Rh‐catalyzed cascade reaction of readily available trifluoromethyl alkene‐tethered benzocyclobutenols is reported. This transformation proceeds via a mechanistically intricate sequence involving CC bond activation, migratory insertion, β ‐hydride elimination, chain walking, and transfer hydrogenation. By modulation of reaction conditions, both intermolecular and intramolecular transfer hydrogenation pathways have been developed, leading to the divergent synthesis of 4‐ β ‐keto‐ and 4‐ β ‐hydroxy‐substituted 3‐trifluoroethyl benzofurans.
{"title":"Divergent Synthesis of 3‐Trifluoroethyl Benzofurans Through Rh‐Catalyzed CC Bond Activation Coupled with Transfer Hydrogenation","authors":"Qi Wang, Qi Tang, Li‐Juan Zhang, Bi‐Qin Wang, Ping Hu, Hai‐Liang Ni, Feijie Song","doi":"10.1002/adsc.9608","DOIUrl":"https://doi.org/10.1002/adsc.9608","url":null,"abstract":"The strategic incorporation of the pharmacologically privileged trifluoroethyl group into the biologically significant benzofuran scaffold offers considerable potential for medicinal and agrochemical applications. Herein, an atom‐economical synthetic approach to 3‐trifluoroethyl benzofurans through Rh‐catalyzed cascade reaction of readily available trifluoromethyl alkene‐tethered benzocyclobutenols is reported. This transformation proceeds via a mechanistically intricate sequence involving CC bond activation, migratory insertion, <jats:italic>β</jats:italic> ‐hydride elimination, chain walking, and transfer hydrogenation. By modulation of reaction conditions, both intermolecular and intramolecular transfer hydrogenation pathways have been developed, leading to the divergent synthesis of 4‐ <jats:italic>β</jats:italic> ‐keto‐ and 4‐ <jats:italic>β</jats:italic> ‐hydroxy‐substituted 3‐trifluoroethyl benzofurans.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"37 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-12-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145759852","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Yan Wang, Zu‐Yu Mo, Xin‐Ru Liu, Si‐Min Gao, Ying‐Ming Pan, Mu‐Xue He, Xian‐Li Ma
Benzotriazoles and benzenesulfonamides arewidely present in various bioactive molecules, so the development of mild and convenientsynthetic strategies to synthesize compounds containing these functional groups is crucial for discovering candidate therapeutic drugs with higher efficacy and fewer side effects. Herein, we report an imidoyl radical‐involved electrochemical method for the difunctionalization of isocyanides with benzotriazoles and benzenesulfonamides, and also realize the electrochemical reaction of isocyanides with benzotriazoles to construct guanidine derivatives. This strategy achieves the difunctionalization of isocyanide under the action of a base, with benzotriazole as the radical precursor and sulfonamide as the nucleophile. Either does not require a chemical oxidant and can be carried out at room temperature.
{"title":"Electrochemical Imidoyl Radical‐Involved Functionalization of Isocyanides to Construct Benzotriazole‐Sulfonamide and Guanidine Derivatives","authors":"Yan Wang, Zu‐Yu Mo, Xin‐Ru Liu, Si‐Min Gao, Ying‐Ming Pan, Mu‐Xue He, Xian‐Li Ma","doi":"10.1002/adsc.70223","DOIUrl":"https://doi.org/10.1002/adsc.70223","url":null,"abstract":"Benzotriazoles and benzenesulfonamides arewidely present in various bioactive molecules, so the development of mild and convenientsynthetic strategies to synthesize compounds containing these functional groups is crucial for discovering candidate therapeutic drugs with higher efficacy and fewer side effects. Herein, we report an imidoyl radical‐involved electrochemical method for the difunctionalization of isocyanides with benzotriazoles and benzenesulfonamides, and also realize the electrochemical reaction of isocyanides with benzotriazoles to construct guanidine derivatives. This strategy achieves the difunctionalization of isocyanide under the action of a base, with benzotriazole as the radical precursor and sulfonamide as the nucleophile. Either does not require a chemical oxidant and can be carried out at room temperature.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"35 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-12-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145759854","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Emma Bodnár, Ferenc Béke, Klára Aradi, Zoltán Novák
The synthesis of aromatic trifluoromethylated scaffolds is of considerable importance in organic chemistry and pharmaceutical research. Herein, a catalytic method with broad functional group tolerance for the construction of aromatic and heteroaromatic trifluoropropynyl derivatives is reported. This methodology is based on a tandem Sonogashira cross‐coupling reaction between an hydrofluoroolefins‐based carbinol and (hetero)aryl iodides. The developed protocol employs inexpensive and commercially available HFO‐1234yf gas to generate a bench‐stable trifluoropropynyl carbinol reagent.
{"title":"Design and Utilization of Stable Hydrofluoroolefin‐Based Trifluoropropynyl Surrogate for Sonogashira Coupling","authors":"Emma Bodnár, Ferenc Béke, Klára Aradi, Zoltán Novák","doi":"10.1002/adsc.70072","DOIUrl":"https://doi.org/10.1002/adsc.70072","url":null,"abstract":"The synthesis of aromatic trifluoromethylated scaffolds is of considerable importance in organic chemistry and pharmaceutical research. Herein, a catalytic method with broad functional group tolerance for the construction of aromatic and heteroaromatic trifluoropropynyl derivatives is reported. This methodology is based on a tandem Sonogashira cross‐coupling reaction between an hydrofluoroolefins‐based carbinol and (hetero)aryl iodides. The developed protocol employs inexpensive and commercially available HFO‐1234yf gas to generate a bench‐stable trifluoropropynyl carbinol reagent.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"15 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-12-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145731727","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Matthias R. Steiner, Johanna M. Uher, Jürgen Lindner, Cordula M. Zeiler, Christian Slugovc
The combination of azole compounds, such as 1‐methylimidazole and oxiranes (e.g., phenyl glycidyl ether) gives carbenoid reactivity at elevated temperatures. Benzoin condensation was performed with 5 mol% azole and 10 mol% oxirane under air at temperatures of 70°C and above, achieving conversions of up to 85% of benzaldehyde and yields of up to 64% of benzoin. The lower benzoin yield is due to the formation of oxidative benzoin follow‐up products under these reaction conditions. A variety of combinations of azole compounds and oxiranes have been shown to catalyze benzoin condensation. Thus, a modular, potentially inexpensive method of generating carbenoid reactivity has been revealed. The proposed mechanism for catalyst formation involves oxirane opening by, for example, 1‐methylimidazole, which forms a zwitterionic methylimidazolium adduct with the oxirane. Then, the acidic proton in the 2‐position of the imidazolium core is deprotonated by the zwitterion's alkoxide releasing the corresponding N‐heterocyclic carbene (NHC). In addition to its primary function, surplus oxirane serves as a scavenger, removing acidic byproducts that are formed from the aldehyde through oxidative NHC catalysis. This property enables benzoin condensation without the exclusion of oxygen. The practical utility of this catalytic system was demonstrated by polymerizing simple bifunctional aldehyde/oxirane monomers—namely, 4‐(2‐oxiranylmethoxy)‐benzaldehyde, 3‐(2‐oxiranylmethoxy)‐benzaldehyde, and vanillin‐based 2‐methoxy‐4‐(2‐oxiranylmethoxy)‐benzaldehyde—using 5 mol% 1‐methylimidazole in a solventless manner and without excluding air. The monomers polymerized via both the formyl and the oxirane groups, yielded thermosets with glass transition temperatures above 100°C.
{"title":"Harnessing Carbenoid Reactivity From Imidazoles and Oxiranes","authors":"Matthias R. Steiner, Johanna M. Uher, Jürgen Lindner, Cordula M. Zeiler, Christian Slugovc","doi":"10.1002/adsc.70218","DOIUrl":"https://doi.org/10.1002/adsc.70218","url":null,"abstract":"The combination of azole compounds, such as 1‐methylimidazole and oxiranes (e.g., phenyl glycidyl ether) gives carbenoid reactivity at elevated temperatures. Benzoin condensation was performed with 5 mol% azole and 10 mol% oxirane under air at temperatures of 70°C and above, achieving conversions of up to 85% of benzaldehyde and yields of up to 64% of benzoin. The lower benzoin yield is due to the formation of oxidative benzoin follow‐up products under these reaction conditions. A variety of combinations of azole compounds and oxiranes have been shown to catalyze benzoin condensation. Thus, a modular, potentially inexpensive method of generating carbenoid reactivity has been revealed. The proposed mechanism for catalyst formation involves oxirane opening by, for example, 1‐methylimidazole, which forms a zwitterionic methylimidazolium adduct with the oxirane. Then, the acidic proton in the 2‐position of the imidazolium core is deprotonated by the zwitterion's alkoxide releasing the corresponding N‐heterocyclic carbene (NHC). In addition to its primary function, surplus oxirane serves as a scavenger, removing acidic byproducts that are formed from the aldehyde through oxidative NHC catalysis. This property enables benzoin condensation without the exclusion of oxygen. The practical utility of this catalytic system was demonstrated by polymerizing simple bifunctional aldehyde/oxirane monomers—namely, 4‐(2‐oxiranylmethoxy)‐benzaldehyde, 3‐(2‐oxiranylmethoxy)‐benzaldehyde, and vanillin‐based 2‐methoxy‐4‐(2‐oxiranylmethoxy)‐benzaldehyde—using 5 mol% 1‐methylimidazole in a solventless manner and without excluding air. The monomers polymerized via both the formyl and the oxirane groups, yielded thermosets with glass transition temperatures above 100°C.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"29 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2025-12-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145731728","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Adam Cieśliński, Artur Przydacz, Anna Skrzyńska, Łukasz Albrecht
Dearomative Higher-Order Cycloaddition
The cover, designed by Adam Cieśliński, depicts a chain of domino tiles, symbolizing the sequential nature of the chemical processes described. The adjacent tiles represent substrates—a 2π-hetero-higherenophile and a 10π-higherene—that, when subjected to NHC catalysis, undergo a higher-order cycloaddition to form a novel product. More information can be found in the Research Article by Anna Skrzyńska, Albrecht Łukasz, and co-workers (10.1002/adsc.70197).
由Adam Cieśliński设计的封面描绘了一连串的多米诺骨牌，象征着所描述的化学过程的顺序性。相邻的瓦片代表底物-一个2π的杂高亲烯试剂和一个10π的高亲烯试剂-当受到NHC催化时，经过高阶环加成形成新产物。更多信息可以在Anna Skrzyńska， Albrecht Łukasz和同事（10.1002/adsc.70197）的研究文章中找到。
{"title":"Front Cover: Dearomative Higher-Order Cycloaddition for the Construction of Dihydropyrimidin-4(1H)-One Scaffold Employing N-Heterocyclic Carbene Catalysis (Adv. Synth. Catal. 23/2025)","authors":"Adam Cieśliński, Artur Przydacz, Anna Skrzyńska, Łukasz Albrecht","doi":"10.1002/adsc.70253","DOIUrl":"10.1002/adsc.70253","url":null,"abstract":"<p><b>Dearomative Higher-Order Cycloaddition</b></p><p>The cover, designed by Adam Cieśliński, depicts a chain of domino tiles, symbolizing the sequential nature of the chemical processes described. The adjacent tiles represent substrates—a 2π-hetero-higherenophile and a 10π-higherene—that, when subjected to NHC catalysis, undergo a higher-order cycloaddition to form a novel product. More information can be found in the Research Article by Anna Skrzyńska, Albrecht Łukasz, and co-workers (10.1002/adsc.70197).\u0000 <figure>\u0000 <div><picture>\u0000 <source></source></picture><p></p>\u0000 </div>\u0000 </figure></p>","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"367 23","pages":""},"PeriodicalIF":4.0,"publicationDate":"2025-12-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://advanced.onlinelibrary.wiley.com/doi/epdf/10.1002/adsc.70253","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145731731","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Tianxing Li , Xinxin Li , Jinfeng Zhang , Hui Jin , Lixin Zhang
An organocatalytic “on‐water” cascade reaction of β‐ketothioesters and β,γ‐unsaturated α‐ketoesters, catalyzed by 0.2 mol% proline‐derived squaramide, delivers 3,4‐dihydropyranones in 74–98% yield with 90–99% ee within 4 h at ambient temperature. Combined NMR and computational studies characterize the product's keto‐enol tautomeric behavior, while synthetic applications include the diastereoselective construction of 3,4‐dihydropyranones featuring an all‐carbon quaternary stereocenter.
{"title":"Enantioselective Synthesis of 3,4‐Dihydropyranones via Low‐Loading Squaramide Catalysis “on Water”","authors":"Tianxing Li , Xinxin Li , Jinfeng Zhang , Hui Jin , Lixin Zhang","doi":"10.1002/adsc.70141","DOIUrl":"10.1002/adsc.70141","url":null,"abstract":"<div><div>An organocatalytic “on‐water” cascade reaction of <em>β</em>‐ketothioesters and <em>β</em>,<em>γ</em>‐unsaturated <em>α</em>‐ketoesters, catalyzed by 0.2 mol% proline‐derived squaramide, delivers 3,4‐dihydropyranones in 74–98% yield with 90–99% ee within 4 h at ambient temperature. Combined NMR and computational studies characterize the product's keto‐enol tautomeric behavior, while synthetic applications include the diastereoselective construction of 3,4‐dihydropyranones featuring an all‐carbon quaternary stereocenter.</div></div>","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"367 23","pages":"Article e70141"},"PeriodicalIF":4.0,"publicationDate":"2025-12-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145235316","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Shaofeng Gong , Sheng‐Hua Wang , Zu‐Li Wang , Wei‐Min He
As efficient nitrogen radical precursors, dioxazolones have emerged as key intermediates in photocatalytic CN bond construction due to their mild reaction conditions, and generation of only CO2 as a byproduct. This review summarizes recent advances in the application of dioxazolones in photocatalytic nitrene transfer reactions, with a focus on synthetic methodologies for diverse amides and their derivatives and the mechanistic insights into different catalytic systems. The aim is to provide guidance for developing green and efficient CN, SN, PN, and SN bond formation strategies and to promote the application of photocatalytic nitrene transfer reactions in pharmaceutical and materials science.
{"title":"Recent Advances in Photocatalytic Transformations of Dioxazolones","authors":"Shaofeng Gong , Sheng‐Hua Wang , Zu‐Li Wang , Wei‐Min He","doi":"10.1002/adsc.70158","DOIUrl":"10.1002/adsc.70158","url":null,"abstract":"<div><div>As efficient nitrogen radical precursors, dioxazolones have emerged as key intermediates in photocatalytic CN bond construction due to their mild reaction conditions, and generation of only CO<sub>2</sub> as a byproduct. This review summarizes recent advances in the application of dioxazolones in photocatalytic nitrene transfer reactions, with a focus on synthetic methodologies for diverse amides and their derivatives and the mechanistic insights into different catalytic systems. The aim is to provide guidance for developing green and efficient CN, SN, PN, and SN bond formation strategies and to promote the application of photocatalytic nitrene transfer reactions in pharmaceutical and materials science.</div></div>","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"367 23","pages":"Article e70158"},"PeriodicalIF":4.0,"publicationDate":"2025-12-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145282761","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Herein, a photoredox‐catalyzed protocol for allylamine hydrocarbamoylation under metal‐free and mild conditions is reported. The proposed method utilizes readily accessible 4‐carboxyamido Hantzsch esters as convenient substrates that deliver carbamoyl radicals upon a visible light‐mediated SET process. Their addition to various allylamines proceeds with good‐to‐excellent efficiency and with high levels of regio‐ and chemoselectivity to provide the corresponding γ‐amino acid amides.
{"title":"Photochemical Metal‐Free Hydrocarbamoylation of Allylamines","authors":"Mariusz Zalewski , Sebastian Stecko","doi":"10.1002/adsc.70148","DOIUrl":"10.1002/adsc.70148","url":null,"abstract":"<div><div>Herein, a photoredox‐catalyzed protocol for allylamine hydrocarbamoylation under metal‐free and mild conditions is reported. The proposed method utilizes readily accessible 4‐carboxyamido Hantzsch esters as convenient substrates that deliver carbamoyl radicals upon a visible light‐mediated SET process. Their addition to various allylamines proceeds with good‐to‐excellent efficiency and with high levels of regio‐ and chemoselectivity to provide the corresponding γ‐amino acid amides.</div></div>","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"367 23","pages":"Article e70148"},"PeriodicalIF":4.0,"publicationDate":"2025-12-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145215816","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
The transformation of aldehydes and ketones into acetals and ketals has garnered significant attention due to their wide applications as fragrances, bio‐oil additives, and organic synthetic intermediates. Conventional acetalization methods, however, often rely on corrosive acids or stoichiometric additives, necessitating harsh conditions and increasing production costs. Here, the development of a phosphorus‐doped carbon catalyst is presented, that enables the acetalization of aldehydes and ketones into acetals and ketals under mild conditions (e.g., 60 °C, atmospheric pressure). This catalyst achieves a high yield of 2‐phenyl‐1,3‐dioxolane (87.1%) from benzaldehyde and exhibits exceptional stability, operating continuously for 120 h in a continuous fixed‐bed reactor. In the continuous reaction, the yield of 2‐phenyl‐1,3‐dioxolane remains over 96% in the first 18 h and slightly decreases to 86% after 120 h of continuous operation. Comprehensive physicochemical characterizations reveal that phosphorus acts as a Lewis acid sites and plays a critical role in modulating the Lewis acid sites of the PC catalysts. This work highlights the significance of optimizing acid properties for the efficient acetalization reaction, offering a promising approach to sustainable chemical synthesis.
{"title":"Cleaner Production of Acetals/Ketals Using a Phosphorus‐Doped Biomass‐Based Carbon Catalyst via Acetalization Reaction","authors":"Yuguo Dong , Shiyun Xiao , Dongsheng Huang , Changle Zhao , Yongdian Xu , Lin Dong , Zupeng Chen , Xiaoli Gu","doi":"10.1002/adsc.70142","DOIUrl":"10.1002/adsc.70142","url":null,"abstract":"<div><div>The transformation of aldehydes and ketones into acetals and ketals has garnered significant attention due to their wide applications as fragrances, bio‐oil additives, and organic synthetic intermediates. Conventional acetalization methods, however, often rely on corrosive acids or stoichiometric additives, necessitating harsh conditions and increasing production costs. Here, the development of a phosphorus‐doped carbon catalyst is presented, that enables the acetalization of aldehydes and ketones into acetals and ketals under mild conditions (e.g., 60 °C, atmospheric pressure). This catalyst achieves a high yield of 2‐phenyl‐1,3‐dioxolane (87.1%) from benzaldehyde and exhibits exceptional stability, operating continuously for 120 h in a continuous fixed‐bed reactor. In the continuous reaction, the yield of 2‐phenyl‐1,3‐dioxolane remains over 96% in the first 18 h and slightly decreases to 86% after 120 h of continuous operation. Comprehensive physicochemical characterizations reveal that phosphorus acts as a Lewis acid sites and plays a critical role in modulating the Lewis acid sites of the PC catalysts. This work highlights the significance of optimizing acid properties for the efficient acetalization reaction, offering a promising approach to sustainable chemical synthesis.</div></div>","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"367 23","pages":"Article e70142"},"PeriodicalIF":4.0,"publicationDate":"2025-12-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145255491","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Yuming Li , Yan Gou , Shanling Hou , Yong Gao , Yaqi Xuan , Zhi Fan
In this article, a Pd(0)/ NaH‐mediated [4 + 4] cascade annulation reaction of 2‐fluoro‐N‐arylbenzenesulfonamides and 2‐methylidenetrimethylene carbonate is developed, providing the benzo[b][1,4,5]oxathiazocine‐1,1‐dioxides in generally excellent yields (71−95%), and some of the enantioenriched products featuring C–N axial chirality are also achieved (up to 88% yield and 60% ee) under mild conditions. Moreover, the synthesized compounds exhibit promising anticancer activity against human cancer cell lines Hela (cervical cancer), highlighting their potential applications for drug screening.
{"title":"One‐Pot Tandem [4 + 4] Annulation of 2‐Fluoro‐N‐arylbenzenesulfonamides with 2‐Methylidenetrimethylene Carbonates: Access to Functionalized Benzoxathiazocines","authors":"Yuming Li , Yan Gou , Shanling Hou , Yong Gao , Yaqi Xuan , Zhi Fan","doi":"10.1002/adsc.70155","DOIUrl":"10.1002/adsc.70155","url":null,"abstract":"<div><div>In this article, a Pd(0)/ NaH‐mediated [4 + 4] cascade annulation reaction of 2‐fluoro‐N‐arylbenzenesulfonamides and 2‐methylidenetrimethylene carbonate is developed, providing the benzo[<em>b</em>][1,4,5]oxathiazocine‐1,1‐dioxides in generally excellent yields (71−95%), and some of the enantioenriched products featuring C–N axial chirality are also achieved (up to 88% yield and 60% ee) under mild conditions. Moreover, the synthesized compounds exhibit promising anticancer activity against human cancer cell lines Hela (cervical cancer), highlighting their potential applications for drug screening.</div></div>","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"367 23","pages":"Article e70155"},"PeriodicalIF":4.0,"publicationDate":"2025-12-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145228925","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
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