Muhammad Faisal Yasin, Ying-Chao Li, Long Zheng, Yichen Wu, Peng Wang
The installation of polyfluoroaryl group in functional molecules is of interest due to the presence of polyfluoroarenes in pharmaceuticals, agrochemicals, and advanced materials. Herein, we report the direct coupling of polyfluoroarenes with acylsilanes for synthesis of fluorinated benzylic alcohols in the presence of a catalytic base. This reaction could tolerate a wide range of polyfluoroarenes and polyfluoroheteroarenes, providing an efficient entry to fluoroarylated compounds. Deuteration experiments showed that the hydrogen source in the product was mainly from the polyfluoroarenes. The utility of this method was demonstrated by the derivations of the product and the synthesis of a fluorinated analogue with antituberculous activity.
{"title":"Direct Coupling of Polyfluoroarenes with Acylsilanes Under Metal-Free Conditions","authors":"Muhammad Faisal Yasin, Ying-Chao Li, Long Zheng, Yichen Wu, Peng Wang","doi":"10.1002/ejoc.202500046","DOIUrl":"https://doi.org/10.1002/ejoc.202500046","url":null,"abstract":"The installation of polyfluoroaryl group in functional molecules is of interest due to the presence of polyfluoroarenes in pharmaceuticals, agrochemicals, and advanced materials. Herein, we report the direct coupling of polyfluoroarenes with acylsilanes for synthesis of fluorinated benzylic alcohols in the presence of a catalytic base. This reaction could tolerate a wide range of polyfluoroarenes and polyfluoroheteroarenes, providing an efficient entry to fluoroarylated compounds. Deuteration experiments showed that the hydrogen source in the product was mainly from the polyfluoroarenes. The utility of this method was demonstrated by the derivations of the product and the synthesis of a fluorinated analogue with antituberculous activity.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"57 55 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-03-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143561258","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Oxadiazine has the distinctive structure of a six-membered heterocyclic ring with two nitrogen and one oxygen atoms. This molecule has lately gained substantial attention due to its promising uses in several sectors, including medicines, agrochemicals, and material science. As a result, the synthesis of oxadiazine has a broad scope due to its uses in biological and chemical properties such as antibacterial, anticancer, anti-inflammatory, and insecticidal acts. In this review, we provided a comprehensive overview of oxadiazine's synthetic strategies and mechanistic aspects, prioritizing the various novel methods developed for synthesising oxadiazine. We demonstrated the synthesis of various oxadiazine derivatives such as 1,3,4-, 1,3,5-, 1,2,4-, 1,2,5-oxadiazines and the functionalization of this molecule to enhance their bioactivity. In this study, we discussed an overview of synthetic routes, such as cyclization reactions, cycloaddition reactions, catalyst-free and solvent-free reactions, triflate-catalyzed reactions, etc. We highlighted the challenges faced in the reported synthesis, suitable reaction conditions, substrate scope and applications.
{"title":"Advancements in the Synthesis of Oxadiazines, Mechanistic insights and Pathways","authors":"Rambabu Dandela, Vijayakumar Hemamalini, Priteeparna Das, Subburethinam Ramesh","doi":"10.1002/ejoc.202500116","DOIUrl":"https://doi.org/10.1002/ejoc.202500116","url":null,"abstract":"Oxadiazine has the distinctive structure of a six-membered heterocyclic ring with two nitrogen and one oxygen atoms. This molecule has lately gained substantial attention due to its promising uses in several sectors, including medicines, agrochemicals, and material science. As a result, the synthesis of oxadiazine has a broad scope due to its uses in biological and chemical properties such as antibacterial, anticancer, anti-inflammatory, and insecticidal acts. In this review, we provided a comprehensive overview of oxadiazine's synthetic strategies and mechanistic aspects, prioritizing the various novel methods developed for synthesising oxadiazine. We demonstrated the synthesis of various oxadiazine derivatives such as 1,3,4-, 1,3,5-, 1,2,4-, 1,2,5-oxadiazines and the functionalization of this molecule to enhance their bioactivity. In this study, we discussed an overview of synthetic routes, such as cyclization reactions, cycloaddition reactions, catalyst-free and solvent-free reactions, triflate-catalyzed reactions, etc. We highlighted the challenges faced in the reported synthesis, suitable reaction conditions, substrate scope and applications.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"91 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-03-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143561257","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
We herein report time-controlled O-C glycoside rearrangement in flow-electrochemical microreactors, focusing on kinetic and thermodynamic selectivity. The selective synthesis of phenolic O- and C-glycosides has been explored using O-C glycoside rearrangement. We investigated the time-control of O-C glycoside rearrangement using a flow microreactor, which allows for second-scale reaction control. The electrochemical approach demonstrated that shortening the residence time leads to the selective synthesis of O-glycosides, while longer times favor the formation of C-glycosides. Kinetic studies revealed that substituents on the phenol ring affect the rate of O-glycoside formation and its rearrangement to C-glycosides. Finally, continuous flow synthesis was demonstrated, showcasing the scalability and utility of this method for producing bioactive substances.
{"title":"O-C Glycoside Rearrangement through Time-Controlled Electrochemical Flow Strategy: Switching between Kinetics and Thermodynamics","authors":"Yosuke Ashikari, Yiyue Yao, Takuma Kudo, Masahiro Takumi, Aiichiro Nagaki","doi":"10.1002/ejoc.202500038","DOIUrl":"https://doi.org/10.1002/ejoc.202500038","url":null,"abstract":"We herein report time-controlled O-C glycoside rearrangement in flow-electrochemical microreactors, focusing on kinetic and thermodynamic selectivity. The selective synthesis of phenolic O- and C-glycosides has been explored using O-C glycoside rearrangement. We investigated the time-control of O-C glycoside rearrangement using a flow microreactor, which allows for second-scale reaction control. The electrochemical approach demonstrated that shortening the residence time leads to the selective synthesis of O-glycosides, while longer times favor the formation of C-glycosides. Kinetic studies revealed that substituents on the phenol ring affect the rate of O-glycoside formation and its rearrangement to C-glycosides. Finally, continuous flow synthesis was demonstrated, showcasing the scalability and utility of this method for producing bioactive substances.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"3 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-03-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143561260","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
A green light-driven, organophosphine-catalyzed iododifluoroalkylation of alkynes using iododifluoroketones has been developed, eliminating the need for additional metal catalysts and bases. This protocol enables the efficient and sustainable synthesis of CF2-derived alkenyl iodides under mild conditions, demonstrating excellent tolerance to iododifluoroketones, iododifluoroesters, and perfluoroalkyl iodides. Preliminary mechanistic studies suggest that the catalytic phosphine functions not only as a Lewis base, forming a charge-transfer complex with difluoroalkyl iodides through halogen-bonding interactions to generate Rf radicals, but also as a halogen transfer shuttle catalyst to facilitate the catalytic cycle.
{"title":"Green Light-Driven Organophosphine-Catalyzed Iododifluoroalkylation of Alkynes","authors":"Shibo Xu, Yicong Li, Tianjing Yu, Jinyu Guo, Yun Cao, Qing Zhang, Chao Liu, Jingjing Wu, Fanhong Wu","doi":"10.1002/ejoc.202500194","DOIUrl":"https://doi.org/10.1002/ejoc.202500194","url":null,"abstract":"A green light-driven, organophosphine-catalyzed iododifluoroalkylation of alkynes using iododifluoroketones has been developed, eliminating the need for additional metal catalysts and bases. This protocol enables the efficient and sustainable synthesis of CF2-derived alkenyl iodides under mild conditions, demonstrating excellent tolerance to iododifluoroketones, iododifluoroesters, and perfluoroalkyl iodides. Preliminary mechanistic studies suggest that the catalytic phosphine functions not only as a Lewis base, forming a charge-transfer complex with difluoroalkyl iodides through halogen-bonding interactions to generate Rf radicals, but also as a halogen transfer shuttle catalyst to facilitate the catalytic cycle.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"53 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-03-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143561259","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Prasanta Roy, Karuna Mahato, Divya Shrestha, Seung Woo Lee
Quinazolinone is a crucial scaffold in numerous natural compounds, as well as in biologically active and functional materials. Consequently, various synthetic methods have been developed to transform quinazolinone and its derivatives. Site selective C−H bond functionalization and annulation of the 2-aryl-quinazolinones skeleton through transition-metal catalysis offer an efficient approach to obtaining diverse substituted nitrogen-containing heterocyclic frameworks. This review summarizes recent reports on transition-metal catalyzed site selective transformations of 2-aryl-quinazolinone through C-H functionalization and annulation reactions.
{"title":"Recent Developments in C-H Functionalization and Annulation of 2-Aryl-Quinazolinonesvia Site Selective Transformations","authors":"Prasanta Roy, Karuna Mahato, Divya Shrestha, Seung Woo Lee","doi":"10.1002/ejoc.202500034","DOIUrl":"https://doi.org/10.1002/ejoc.202500034","url":null,"abstract":"Quinazolinone is a crucial scaffold in numerous natural compounds, as well as in biologically active and functional materials. Consequently, various synthetic methods have been developed to transform quinazolinone and its derivatives. Site selective C−H bond functionalization and annulation of the 2-aryl-quinazolinones skeleton through transition-metal catalysis offer an efficient approach to obtaining diverse substituted nitrogen-containing heterocyclic frameworks. This review summarizes recent reports on transition-metal catalyzed site selective transformations of 2-aryl-quinazolinone through C-H functionalization and annulation reactions.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"8 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-03-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143546814","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Chun-Yu Nong, Xiu-Qing Mo, Jin-He Zhao, Lu Lei, Lu Ma, Dong-Liang Mo
A variety of isooxazoline-fused furo[3,2-b]quinolines containing four stereocenters were prepared in 40%-87% yields with high regioselectivity and diastereoselectivity. The control experimental results revealed that the reaction underwent in the order of [4+2] cycloaddition and sequential [3+2] cycloaddition between aza-ortho-quinone methides (ao-QM) generated from 2-chloromethyl anilines, furan, and nitrile N-oxides generated from hydroxamoyl chlorides. The present method features mild reaction conditions, broad substrate scope, high diastereoselectivity of four stereocenters, and novel scaffolds of isooxazoline-fused furo[3,2-b]quinolines.
{"title":"Three-Component Cycloadditions to prepare Isooxazoline-Fused Furo[3,2-b]quinolines","authors":"Chun-Yu Nong, Xiu-Qing Mo, Jin-He Zhao, Lu Lei, Lu Ma, Dong-Liang Mo","doi":"10.1002/ejoc.202500007","DOIUrl":"https://doi.org/10.1002/ejoc.202500007","url":null,"abstract":"A variety of isooxazoline-fused furo[3,2-b]quinolines containing four stereocenters were prepared in 40%-87% yields with high regioselectivity and diastereoselectivity. The control experimental results revealed that the reaction underwent in the order of [4+2] cycloaddition and sequential [3+2] cycloaddition between aza-ortho-quinone methides (ao-QM) generated from 2-chloromethyl anilines, furan, and nitrile N-oxides generated from hydroxamoyl chlorides. The present method features mild reaction conditions, broad substrate scope, high diastereoselectivity of four stereocenters, and novel scaffolds of isooxazoline-fused furo[3,2-b]quinolines.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"52 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-03-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143539333","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
This notification is for the above article, published online on December 2006 in Wiley Online Library (wileyonlinelibrary.com), and has been issued by agreement between the journal Editor-in-Chief, Anne Nijs; the publishing Chemistry Europe societies; and Wiley-VCH GmbH. This notification has been issued in response to concerns raised by third parties.1 The article presents experiments in a non-verifiable cell line, “BGC-803”. As the authors could not be reached to clarify this issue, the journal has decided to publish this notification to inform and alert readers.
{"title":"Notification: NOTIFICATION: Hopeanol: A Potent Cytotoxin with A Novel Skeleton from Hopea exalata","authors":"","doi":"10.1002/ejoc.202500185","DOIUrl":"https://doi.org/10.1002/ejoc.202500185","url":null,"abstract":"<p>This notification is for the above article, published online on December 2006 in Wiley Online Library (wileyonlinelibrary.com), and has been issued by agreement between the journal Editor-in-Chief, Anne Nijs; the publishing Chemistry Europe societies; and Wiley-VCH GmbH. This notification has been issued in response to concerns raised by third parties.<span><sup>1</sup></span> The article presents experiments in a non-verifiable cell line, “BGC-803”. As the authors could not be reached to clarify this issue, the journal has decided to publish this notification to inform and alert readers.</p>","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"32 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-02-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143518305","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Herein, we report a Pd(II)–catalyzed highly regiospecific ortho–hydroxylation of N–nitrosoanilines utilizing tert–butyl hydroperoxide (TBHP) as the hydroxylating source. The reaction proceeds through N–nitroso group directed C–H activation and subsequent hydroxylation at the ortho–position. The protocol provides a mild, operationally straightforward, and high–yielding transformation, offering a valuable tool for the construction of ortho–hydroxylated aniline derivatives, which are important intermediates in pharmaceutical and materials chemistry.
{"title":"ortho–Hydroxylation of N–Nitrosoanilines Using Palladium Acetate and TBHP","authors":"Saroj Ranjan De, Sandeep Singh","doi":"10.1002/ejoc.202500057","DOIUrl":"https://doi.org/10.1002/ejoc.202500057","url":null,"abstract":"Herein, we report a Pd(II)–catalyzed highly regiospecific ortho–hydroxylation of N–nitrosoanilines utilizing tert–butyl hydroperoxide (TBHP) as the hydroxylating source. The reaction proceeds through N–nitroso group directed C–H activation and subsequent hydroxylation at the ortho–position. The protocol provides a mild, operationally straightforward, and high–yielding transformation, offering a valuable tool for the construction of ortho–hydroxylated aniline derivatives, which are important intermediates in pharmaceutical and materials chemistry.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"16 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-02-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143518306","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
π-Conjugated organic compounds display unique optical and electrical properties, rendering them appropriate for semiconducting applications. Knoevenagel condensation is one of the important reactions that facilitate the formation of olefin linkages (-C=C-) and thus has been widely employed to synthesize new π-conjugated molecules. This review summarizes the synthesis of π-conjugated compounds constructed using four novel π-conjugated moieties: diketonate/azopyrrole-BF2 complexes (BF), p-azaquinodimethane (AQM), diketopyrrolopyrrole (DPP), and barbituric acid (BA), alongside their optoelectronic features and applications in sensing, bioimaging, and photovoltaic technologies.
{"title":"Structure-Property Evaluation of Knoevenagel-derived π-Conjugated Organic Systems","authors":"Vellanki Lakshmi, Maruti Vibhuti Ravikumar, Aswani K Raj, Malakalapalli Rajeswara Rao","doi":"10.1002/ejoc.202401367","DOIUrl":"https://doi.org/10.1002/ejoc.202401367","url":null,"abstract":"π-Conjugated organic compounds display unique optical and electrical properties, rendering them appropriate for semiconducting applications. Knoevenagel condensation is one of the important reactions that facilitate the formation of olefin linkages (-C=C-) and thus has been widely employed to synthesize new π-conjugated molecules. This review summarizes the synthesis of π-conjugated compounds constructed using four novel π-conjugated moieties: diketonate/azopyrrole-BF2 complexes (BF), p-azaquinodimethane (AQM), diketopyrrolopyrrole (DPP), and barbituric acid (BA), alongside their optoelectronic features and applications in sensing, bioimaging, and photovoltaic technologies.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"28 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-02-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143518307","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Leifeng Wang, Yue Wu, Tingwei Gu, Jing Zhao, Binbin Li
Amino acids play a significant role in the study of life sciences, pharmaceutical R&D, bioengineering, and so on. Artificial amino acid-based drugs are important in advancing therapeutic innovation including chronic pain, diabetes, and Alzheimer's disease. Multicomponent reactions (MCRs) are demonstrated to be a powerful strategy for the construction of complicated structures from readily accessible starting reagents in one pot. Thus, applying multicomponent reactions to the preparation of amino acids and derivatives can be a potent strategy for advancing the research of pharmaceutical chemistry. With the rapid development of various catalytic methods and multicomponent reactions, this review outlines recent construction methods of amino acid derivatives by transition metal-catalyzed, light-mediated and other organocatalytic multicomponent reactions.
{"title":"Recent Advances in the Synthesis of Amino Acid Derivatives through Multicomponent Reactions","authors":"Leifeng Wang, Yue Wu, Tingwei Gu, Jing Zhao, Binbin Li","doi":"10.1002/ejoc.202401299","DOIUrl":"https://doi.org/10.1002/ejoc.202401299","url":null,"abstract":"Amino acids play a significant role in the study of life sciences, pharmaceutical R&D, bioengineering, and so on. Artificial amino acid-based drugs are important in advancing therapeutic innovation including chronic pain, diabetes, and Alzheimer's disease. Multicomponent reactions (MCRs) are demonstrated to be a powerful strategy for the construction of complicated structures from readily accessible starting reagents in one pot. Thus, applying multicomponent reactions to the preparation of amino acids and derivatives can be a potent strategy for advancing the research of pharmaceutical chemistry. With the rapid development of various catalytic methods and multicomponent reactions, this review outlines recent construction methods of amino acid derivatives by transition metal-catalyzed, light-mediated and other organocatalytic multicomponent reactions.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"20 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-02-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143518309","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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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