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Rh(III)-Catalyzed Cascade [3+3] Spiroannulation of N-Acyl Ketimines with Iodonium Ylides: Access to Spiro-N,O-Ketals
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-03-25 DOI: 10.1002/ejoc.202500155
Jiaojiao Wen, Xia Zhang, Chao Pi, Yangjie Wu, Xiuling Cui
{"title":"Rh(III)-Catalyzed Cascade [3+3] Spiroannulation of N-Acyl Ketimines with Iodonium Ylides: Access to Spiro-N,O-Ketals","authors":"Jiaojiao Wen, Xia Zhang, Chao Pi, Yangjie Wu, Xiuling Cui","doi":"10.1002/ejoc.202500155","DOIUrl":"https://doi.org/10.1002/ejoc.202500155","url":null,"abstract":"A Rh(III)-catalyzed cascade C-H activation/[3+3]spiroannulation of 3-hydroxy-3-arylisoindolin-1-ones with iodonium ylides has been developed. The method facilitates the efficient and selective construction of spirocyclic compounds in a one-pot manner, offering high yields and excellent conversion. The reaction proceeds via a highly regioselective process, resulting in the formation of spiro-N,O-ketals with remarkable chemo- and stereoselectivity. This strategy provides a valuable protocol for the synthesis of complex spirocyclics with potential applications in medicinal chemistry and materials science.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"16 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-03-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143695854","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}
引用次数: 0
Amphiphilic Fluoro-Functionalized Cellulosic Materials: Synthesis, Characterization and Organic Dye Adsorption Properties
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-03-25 DOI: 10.1002/ejoc.202500035
Davide Ricci, Andrea Maio, Christian Jahns, Elena Piacenza, Delia Francesca Chillura Martino, Roberto Scaffaro, Margit Schulze, Andrea Pace, Carla Rizzo, Ivana Pibiri
{"title":"Amphiphilic Fluoro-Functionalized Cellulosic Materials: Synthesis, Characterization and Organic Dye Adsorption Properties","authors":"Davide Ricci, Andrea Maio, Christian Jahns, Elena Piacenza, Delia Francesca Chillura Martino, Roberto Scaffaro, Margit Schulze, Andrea Pace, Carla Rizzo, Ivana Pibiri","doi":"10.1002/ejoc.202500035","DOIUrl":"https://doi.org/10.1002/ejoc.202500035","url":null,"abstract":"The growing interest towards biopolymers application in amphiphilic conditions prompted us to explore the preparation of fluorinated cellulosic materials. Cellulose (CE) and carboxymethylcellulose (CMC) were functionalized with highly fluorinated pendants, through a nucleophilic aromatic substitution on 3-pentadecafluoroheptyl-5-pentafluorophenyl-1,2,4-oxadiazole (FOX). leading to the corresponding fluorinated biopolymers CE-FOX and CMC-FOX. Structural and thermal stability confirmed covalent attachment of the fluorinated moiety onto the cellulosic skeleton and highlighted an interesting two-dimensional texture of the CMC-FOX material. Hybrid and amphiphilic features of CE-FOX and CMC-FOX, were confirmed by water and oil contact angle measurements (WCA/OCA). Applications as adsorbent material for organic contaminants from an aqueous solution was tested by previously incorporating the functional biopolymer into sodium alginate (SA) hydrogel beads. Rhodamine B (RhB) was used as a model wastewater pollutant. Fluoro-functionalization led to a three- to eightfold increase in the dye-removal efficiency of the SA-incorporated biopolymer with respect to the corresponding non-fluorinated material (from 11% to 48% for SA/CE vs SA/CE-FOX beads and from 11% to 94% for SA/CMC vs SA/CMC-FOX beads). Recyclability tests showed good residual performance of SA/CMC-FOX beads after seven desorption/reuse cycles opening the way to more sustainable adsorbing processes for the removal of emerging pollutants from contaminated water.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"33 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-03-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143695908","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}
引用次数: 0
Visible-Light-Driven E-selective Semihydrogenation and Its Application in the Treatment of Glioblastoma Multiforme
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-03-25 DOI: 10.1002/ejoc.202401370
Jinfei Yang, Huihui Yang, Xianglong Wang, Siqi Chen, Shutang Li, Baohu Li, Yanrui Fan, Haoze He, Zhou Lin
{"title":"Visible-Light-Driven E-selective Semihydrogenation and Its Application in the Treatment of Glioblastoma Multiforme","authors":"Jinfei Yang, Huihui Yang, Xianglong Wang, Siqi Chen, Shutang Li, Baohu Li, Yanrui Fan, Haoze He, Zhou Lin","doi":"10.1002/ejoc.202401370","DOIUrl":"https://doi.org/10.1002/ejoc.202401370","url":null,"abstract":"A visible-light-driven E-selective semihydrogenation scheme of alkyne compounds was developed for designing and synthesizing glioblastoma multiforme (GBM) inhibitors. In the present study, room-temperature semihydrogenation reactions of various alkyne compounds were successfully achieved under the irradiation of white light. The representative reaction mechanism was decoded through theoretical calculations and deuteration experiments, revealing the critical roles played by [Ir(Cp-Me5)Cl2]2, PdCl2, DPPE and TEOA as photosensitizer, catalyst, ligand, and electron donor, respectively. Our method exhibits excellent E-selectivity and broad functional group compatibility, and demonstrates its practical value by producing pinosylvin and its derivatives with strong inhibitory effects on U87 cells.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"35 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-03-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143703589","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}
引用次数: 0
Synthesis and reactivity of 1,4-ethano-1,5-naphthyridine derivatives using microwave activation or flow chemistry
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-03-25 DOI: 10.1002/ejoc.202401443
Mazarine Laurent, Rodolphe Vatinel, Stéphane Bostyn, Sylvain Routier, Frederic Buron
{"title":"Synthesis and reactivity of 1,4-ethano-1,5-naphthyridine derivatives using microwave activation or flow chemistry","authors":"Mazarine Laurent, Rodolphe Vatinel, Stéphane Bostyn, Sylvain Routier, Frederic Buron","doi":"10.1002/ejoc.202401443","DOIUrl":"https://doi.org/10.1002/ejoc.202401443","url":null,"abstract":"The design of some novel disubstituted 3,4-dihydro-2H-1,4-ethano-1,5-naphthyridine derivatives is reported under classical and flow methodologies. The series were developed from quinuclidinone, which afforded versatile platforms bearing one lactam function in position C-2 that was then used to create C–N bond using the Chan-Lam coupling reaction or in situ C–O bond activation via palladium-catalyzed cross-coupling reactions. The conditions were optimized, and a wide range of boronic acids were used to determine the scope and limitations of each method. To complete this study, a flow Suzuki-Miyaura process was established to afford polyfunctionalized 1,4-ethano-1,5-naphthyridine derivatives in high yields with a very efficient process (10 min.).","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"10 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-03-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143695852","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}
引用次数: 0
Harnessing Electricity in Dehydrogenative Coupling: Transition Metal-Free Synthesis of Quinoline Derivatives
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-03-25 DOI: 10.1002/ejoc.202500316
Raju Dey, Vageesh M, Abhijeet Anand, Subir Panja
{"title":"Harnessing Electricity in Dehydrogenative Coupling: Transition Metal-Free Synthesis of Quinoline Derivatives","authors":"Raju Dey, Vageesh M, Abhijeet Anand, Subir Panja","doi":"10.1002/ejoc.202500316","DOIUrl":"https://doi.org/10.1002/ejoc.202500316","url":null,"abstract":"An efficient strategy is demonstrated for the electrocatalyitc synthesis of 2-aryl quinoline derivatives via an anodic dehydrogenation of 2-aminobenzyl alcohol molecules followed by condensation with carbonyl compounds at room temperature. The current protocol requires only electricity as the green oxidant, provides the desired products in good to excellent yield and is compatible with a wide range of functional groups.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"21 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-03-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143695853","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}
引用次数: 0
Halogen‐Mediated Electrochemical C−N Bond Construction of Amine
IF 2.5 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-03-24 DOI: 10.1002/ejoc.202401352
Yu‐Yang Xie , Zhang Zhang , Ying‐Chun Wang
{"title":"Halogen‐Mediated Electrochemical C−N Bond Construction of Amine","authors":"Yu‐Yang Xie ,&nbsp;Zhang Zhang ,&nbsp;Ying‐Chun Wang","doi":"10.1002/ejoc.202401352","DOIUrl":"10.1002/ejoc.202401352","url":null,"abstract":"<div><div>Organic electrochemical synthesis stands out for its environmentally friendly and efficient characteristics. Among these approaches, halogen‐mediated indirect electrosynthesis has gained significant attention as an efficient strategy for C−N bond formation, widely applied in the synthesis of nitrogen‐containing compounds. This review highlights recent advances in direct C−N bond formation processes for various amines under halogen‐mediated electrosynthetic conditions. The features, scope, limitations, and proposed mechanisms of these transformations are discussed in detail. We aim to provide insights into expanding the applicability of halogen‐mediated electrosynthesis, contributing to the development of sustainable synthetic methodologies.</div></div>","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"28 12","pages":"Article e202401352"},"PeriodicalIF":2.5,"publicationDate":"2025-03-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143055274","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}
引用次数: 0
Recent Advances in the Photochemical Synthesis of Esters
IF 2.5 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-03-24 DOI: 10.1002/ejoc.202401398
Jie Li , Dr. Da‐Liang Zhu , David James Young , Prof. Dr. Yanqing Wang , Prof. Dr. Hong‐Xi Li
{"title":"Recent Advances in the Photochemical Synthesis of Esters","authors":"Jie Li ,&nbsp;Dr. Da‐Liang Zhu ,&nbsp;David James Young ,&nbsp;Prof. Dr. Yanqing Wang ,&nbsp;Prof. Dr. Hong‐Xi Li","doi":"10.1002/ejoc.202401398","DOIUrl":"10.1002/ejoc.202401398","url":null,"abstract":"<div><div>Photocatalysis has recently emerged as a powerful synthetic tool for making a variety of carbon‐carbon and carbon‐heteroatom bonds. The development of esterification reactions induced by light is an atom economical and energy efficient alternative to traditional methods for the synthesis of esters, with benefits including mild reaction conditions, high chemical yields, and wide functional group tolerance. This review summarizes recent progress made in this green methodology, including mechanisms of action, substrate scope, limitations and future prospects.</div></div>","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"28 12","pages":"Article e202401398"},"PeriodicalIF":2.5,"publicationDate":"2025-03-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143192371","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}
引用次数: 0
Front Cover: Cardo Bisphenol Fluorene Fused with Dibenzo[g,p]chrysene for a High Refractive Index Monomer (Eur. J. Org. Chem. 11/2025)
IF 2.5 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-03-24 DOI: 10.1002/ejoc.202581101
Toko Yura, Rion Noda, Ikuma Okada, Zhenfeng Guo, Prof. Dr. Takashi Nakanishi, Prof. Dr. Yousuke Yamaoka, Prof. Dr. Tetsuo Iwasawa
{"title":"Front Cover: Cardo Bisphenol Fluorene Fused with Dibenzo[g,p]chrysene for a High Refractive Index Monomer (Eur. J. Org. Chem. 11/2025)","authors":"Toko Yura,&nbsp;Rion Noda,&nbsp;Ikuma Okada,&nbsp;Zhenfeng Guo,&nbsp;Prof. Dr. Takashi Nakanishi,&nbsp;Prof. Dr. Yousuke Yamaoka,&nbsp;Prof. Dr. Tetsuo Iwasawa","doi":"10.1002/ejoc.202581101","DOIUrl":"10.1002/ejoc.202581101","url":null,"abstract":"<p><b>The Front Cover</b> shows a cardo-typed optical material with a high refractive index (1.83) that bends and focuses light. A heptacycle precursor from fused dibenzo[<i>g</i>,<i>p</i>]chrysene (DBC) and cyclopentanone underwent double arylation to yield a cardo scaffold comparable to bis-phenol fluorene. A DBC core with a bay-ester underwent intramolecular acylation and twofold arylation to afford a DBC-linked bisphenol. Achieving a high refractive index with purely hydrocarbons supports future cardo material chemistry. More information can be found in the Research Article by T. Iwasawa and co-workers (DOI: 10.1002/ejoc.202401409).\u0000 <figure>\u0000 <div><picture>\u0000 <source></source></picture><p></p>\u0000 </div>\u0000 </figure>\u0000 </p>","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"28 11","pages":""},"PeriodicalIF":2.5,"publicationDate":"2025-03-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/ejoc.202581101","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143678353","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Photoinduced, Decarboxylative Coupling of α‐Keto Acids with Diselenides to Form Selenoesters α-酮酸与二硒酸酯光诱导脱羧偶联生成硒酸酯
IF 2.5 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-03-24 DOI: 10.1002/ejoc.202401399
Pei Qu , Haifan Wang , Ying Chen , Kanta Pajujantaro , Dr. Gong‐Qing Liu
{"title":"Photoinduced, Decarboxylative Coupling of α‐Keto Acids with Diselenides to Form Selenoesters","authors":"Pei Qu ,&nbsp;Haifan Wang ,&nbsp;Ying Chen ,&nbsp;Kanta Pajujantaro ,&nbsp;Dr. Gong‐Qing Liu","doi":"10.1002/ejoc.202401399","DOIUrl":"10.1002/ejoc.202401399","url":null,"abstract":"<div><div>A mild and green strategy for the synthesis of selenoester derivatives has been developed through photoinduced decarboxylative coupling of α‐keto acids with diselenides. This transformation proceeds smoothly without requiring any external photocatalyst, additive, or oxidant. Both diaryl and dialkyl diselenides react efficiently with α‐keto acids to produce selenoesters in good yields. Mechanistic studies suggest that the generated acyl radical is responsible for this transformation.</div></div>","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"28 12","pages":"Article e202401399"},"PeriodicalIF":2.5,"publicationDate":"2025-03-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142929702","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}
引用次数: 0
An Efficient Synthetic Methodology for the Preparation of Glycosyl β‐diketones 一种制备糖基β-二酮的高效合成方法
IF 2.5 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-03-24 DOI: 10.1002/ejoc.202401366
Ivan A. Barri , Macarena S. Le Pors , Prof. Dr. Pedro A. Colinas
{"title":"An Efficient Synthetic Methodology for the Preparation of Glycosyl β‐diketones","authors":"Ivan A. Barri ,&nbsp;Macarena S. Le Pors ,&nbsp;Prof. Dr. Pedro A. Colinas","doi":"10.1002/ejoc.202401366","DOIUrl":"10.1002/ejoc.202401366","url":null,"abstract":"<div><div>In this study, we present a synthetic methodology for preparing glycosyl β‐diketones from the corresponding allyl ethers. The process involves three steps: nitrile oxide cycloadditions, reduction of the glycosyl isoxazolines, and oxidation of β‐hydroxyketones. This route is suitable for acid‐ and base‐sensitive protecting groups, and the reactions were conducted with retention of the anomeric configuration. The resulting glycosyl β‐diketones were then utilized in the synthesis of the corresponding pyrazoles.</div></div>","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"28 12","pages":"Article e202401366"},"PeriodicalIF":2.5,"publicationDate":"2025-03-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142874612","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}
引用次数: 0
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