发布求助
文献互助 智能选刊 最新文献

European Journal of Organic Chemistry最新文献

筛选
英文 中文
Cross-Coupling Reactions in Aqueous Micellar Media 水性胶束介质中的交叉偶联反应
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-06-17 DOI: 10.1002/ejoc.202500499
Alexander Uner, Liam Thomas Ball
{"title":"Cross-Coupling Reactions in Aqueous Micellar Media","authors":"Alexander Uner, Liam Thomas Ball","doi":"10.1002/ejoc.202500499","DOIUrl":"https://doi.org/10.1002/ejoc.202500499","url":null,"abstract":"Thanks to their ability to efficiently and reliably construct carbon-carbon and carbon-heteroatom bonds, cross-coupling reactions remain at the forefront of chemical research in both academic and industrial settings. However, the growing emphasis on sustainability has exposed the shortcomings of cross-coupling chemistry in several areas, including the preponderance towards toxic polar aprotic solvents, high loadings of precious metal catalysts, and production of large quantities of waste. In recent years, micellar reaction media, formed by dissolution of surfactant molecules in water, have emerged as a sustainable alternative to organic solvents, allowing for use of water as the bulk medium while circumventing the usual solubility issues associated with its use. This Review introduces the fundamentals of surfactants for synthesis and summarises recent advances in cross-coupling chemistry in micellar media, with a focus on improving both sustainability and reaction performance using micellar technologies.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"14 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-06-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144305562","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
Ni(OAc)2 Catalyzed N‐Formylation of Primary Sulfonamides Using Carbon Dioxide at Ambient Pressure 常压下Ni(OAc)2催化伯胺N -甲酰化反应的研究
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-06-16 DOI: 10.1002/ejoc.202500369
David Izuchukwu Ugwu, Ganesh Chandra Upreti, Ashish Garg, Anand Singh
{"title":"Ni(OAc)2 Catalyzed N‐Formylation of Primary Sulfonamides Using Carbon Dioxide at Ambient Pressure","authors":"David Izuchukwu Ugwu, Ganesh Chandra Upreti, Ashish Garg, Anand Singh","doi":"10.1002/ejoc.202500369","DOIUrl":"https://doi.org/10.1002/ejoc.202500369","url":null,"abstract":"A Ni(OAc)2 catalysed N‐formylation of primary sulfonamides using gaseous carbon dioxide is reported. A range of aromatic, heteroaromatic, and aliphatic sulfonamides were formylated under ambient pressure of carbon dioxide in a closed system. This redox neutral method represents a mechanistically novel and operationally convenient method for employing carbon dioxide as a formyl equivalent.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"13 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-06-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144296199","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
Green Approach for Copper‐Free Pd‐catalyzed Sonogashira Cross‐Coupling using Saponin‐Based Micellar Catalysis in Water at Ambient Temperature 室温下用水皂素胶束催化无铜钯催化Sonogashira交叉偶联的绿色途径
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-06-16 DOI: 10.1002/ejoc.202500436
Vinothkumar Vinayagam, Subir Kumar Sadhukhan, Maroju Ravi Kumar, Nooka Raju Anisetti, Chittem Rajashekar Reddy
{"title":"Green Approach for Copper‐Free Pd‐catalyzed Sonogashira Cross‐Coupling using Saponin‐Based Micellar Catalysis in Water at Ambient Temperature","authors":"Vinothkumar Vinayagam, Subir Kumar Sadhukhan, Maroju Ravi Kumar, Nooka Raju Anisetti, Chittem Rajashekar Reddy","doi":"10.1002/ejoc.202500436","DOIUrl":"https://doi.org/10.1002/ejoc.202500436","url":null,"abstract":"A micellar catalysis that is derived from commercially available saponin for copper‐free, Pd‐catalyzed Sonogashira cross‐coupling under mild reaction conditions has been developed. Using this green and sustainable method, a broad range of aryl/heteroaryl and alkyl terminal alkynes were cross‐coupled with aryl/heteroaryl halides at ambient temperature in an aqueous medium. The commercially available, inexpensive, and plant‐based natural saponin served as a surfactant for a micellar system that effectively enabled C(sp2)‐C(sp) cross‐coupling with a wide range of substrates. The attractive features of this protocol are the use of water as a reaction medium, the in‐situ generation of the micellar‐catalysis system from biodegradable natural saponins, good functional group tolerance, scalability of the products, and notably the ability to retain the catalyst activity by recycling the aqueous reaction medium.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"2 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-06-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144296189","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
Formal Higher‐Order [8 + 3] Cycloaddition of Azaheptafulvenes with Donor‐Acceptor Cyclopropanes 氮杂七烯与供体-受体环丙烷的正式高阶[8 + 3]环加成
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-06-16 DOI: 10.1002/ejoc.202500331
Junjie Xi, Wang Liu, Guochun Li, Xiaoyan Zhang, Yujiao Xiang, Yonghai Hui, Xin Zhou, Weiliang Chen, Yungui Peng
{"title":"Formal Higher‐Order [8 + 3] Cycloaddition of Azaheptafulvenes with Donor‐Acceptor Cyclopropanes","authors":"Junjie Xi, Wang Liu, Guochun Li, Xiaoyan Zhang, Yujiao Xiang, Yonghai Hui, Xin Zhou, Weiliang Chen, Yungui Peng","doi":"10.1002/ejoc.202500331","DOIUrl":"https://doi.org/10.1002/ejoc.202500331","url":null,"abstract":"Cyclohepta[b]pyridine derivatives have attracted significant attention owing to their unique bioactivities. Herein, we describe an efficient method to access various cyclohepta[b]pyridine derivatives through formal higher‐order [8+3] cycloaddition of azaheptafulvenes with donor‐acceptor cyclopropanes catalyzed by Yb(OTf)3. This method exhibited broad substrate accommodation and gave the corresponding products in high yields and selectivity.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"11 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-06-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144296174","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
Organocatalytic Halogenation of Aromatic and Heteroaromatic Compounds 芳香族和杂芳香族化合物的有机催化卤化
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-06-14 DOI: 10.1002/ejoc.202500125
Paola Andrea Acosta-Guzman, Alexander Garay-Talero, Diego Gamba-Sanchez
{"title":"Organocatalytic Halogenation of Aromatic and Heteroaromatic Compounds","authors":"Paola Andrea Acosta-Guzman, Alexander Garay-Talero, Diego Gamba-Sanchez","doi":"10.1002/ejoc.202500125","DOIUrl":"https://doi.org/10.1002/ejoc.202500125","url":null,"abstract":"The halogenation of aromatic and heteroaromatic systems has attracted considerable attention in recent decades owing to the importance of haloaromatics in biologically relevant compounds and their role as essential building blocks for more complex systems. In recent years, various research groups have explored the challenge of developing new synthetic methodologies for electrophilic halogenation. Nevertheless, these methods continue to encounter several challenges, such as waste products from halogenating agents, toxic or contaminating reagents, and problems with low regioselectivity, with polyhalogenation—often the predominant side reaction—occurring in some cases. In this context, organocatalysis has emerged as a promising approach to address these limitations. This review highlights key organocatalytic strategies reported in the last 14 years and discusses experimental aspects, mechanisms, and selectivity issues in chlorination, bromination, fluorination, and iodination of aromatic systems.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"308 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-06-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144288284","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
Hydrogen peroxide ‐ responsive aminoferrocene prodrugs 过氧化氢反应性氨基二茂前药
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-06-14 DOI: 10.1002/ejoc.202500294
Marlies Körber, Jennifer Rühle, Fabian Halter, Andriy Mokhir
{"title":"Hydrogen peroxide ‐ responsive aminoferrocene prodrugs","authors":"Marlies Körber, Jennifer Rühle, Fabian Halter, Andriy Mokhir","doi":"10.1002/ejoc.202500294","DOIUrl":"https://doi.org/10.1002/ejoc.202500294","url":null,"abstract":"Aminoferrocene (AF)‐based prodrugs are activated in cancer cells through reactions with H₂O₂ and other reactive oxygen species (ROS), generating electron‐rich AF’s. These, in turn, induce the production of highly toxic O2·‐ and HO·, leading to cancer cell death. Effective activation of these prodrugs depends on their ability to target intracellular organelles rich in ROS, as non‐targeted prodrugs are practically inactive. In this study, we replaced the boronic acid pinacol ester—previously used as a ROS‐trigger—with an α‐ketoamide fragment, which is more selective and sensitive to H₂O₂. This modification enhanced the anticancer efficacy of untargeted AF prodrugs, reducing the IC₅₀ from 23.9–35.5 μM (previously reported prodrug 13b) to 5–6.4 μM (new prodrug 2a) in human ovarian cancer A2780 and Burkitt’s lymphoma BL‐2 cells. Further analysis confirmed that the anticancer effect of 2a is driven by its ability to markedly increase intracellular ROS levels in both the cytoplasm and mitochondria.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"37 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-06-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144289826","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
Photocatalyst‐ and Oxidant‐Free Photoinduced Radical Cascade for the Synthesis of Difluoromethylated Dihydroisoquinolones from N‐Allylbenzamides N -烯丙基苯酰胺合成二氟甲基化二氢异喹诺酮类药物的光催化和无氧化剂光诱导自由基级联反应
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-06-14 DOI: 10.1002/ejoc.202500214
Bo-Mi Long, Guang-Lin Lu, Zhengshuang Xu, Guo-Kai Liu
{"title":"Photocatalyst‐ and Oxidant‐Free Photoinduced Radical Cascade for the Synthesis of Difluoromethylated Dihydroisoquinolones from N‐Allylbenzamides","authors":"Bo-Mi Long, Guang-Lin Lu, Zhengshuang Xu, Guo-Kai Liu","doi":"10.1002/ejoc.202500214","DOIUrl":"https://doi.org/10.1002/ejoc.202500214","url":null,"abstract":"A mild photocatalyst‐ and oxidant‐free photoinduced reaction for the convenient synthesis of difluoromethylated dihydroisoquinolones from N‐allylbenzamides with a difluoromethyl phenoxathiinium salt (CF2H‐PXT+) is presented, which involves a radical difluoromethylation/cyclization cascade process with broad substrate scope and good functional‐group tolerance. Using this method, a broad range of N‐allylbenzamides were successfully converted to the desired difluoromethylated dihydroisoquinolones in good to high yields.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"20 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-06-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144289785","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
Facile Synthesis of 5-Halo-1,2,3-triazole-fused Benzotricyclic Frameworks from 1-(ω-Azidoalkyl)-2-(2,2-dihalovinyl)arenes and their Application in Fluorescent Triazole Derivatives 1-（ω-叠氮烷基）-2-（2,2-二卤乙烯基）芳烃催化合成5- halo -1,2,3-三唑-并杂三环骨架及其在荧光三唑衍生物中的应用
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-06-13 DOI: 10.1002/ejoc.202500355
Takeshi Hata, Seiya Kikukawa, Miki Ebihara, Kazuki Kobayashi, Nozomi Kasakura, Takashi Kanamori, Tadaomi Furuta, Ai Kohata, Nobuaki Funahashi, Shota Matsumoto, Satoru Karasawa, Kazushi Kinbara, Naohiko Koshikawa, Hideya Yuasa
{"title":"Facile Synthesis of 5-Halo-1,2,3-triazole-fused Benzotricyclic Frameworks from 1-(ω-Azidoalkyl)-2-(2,2-dihalovinyl)arenes and their Application in Fluorescent Triazole Derivatives","authors":"Takeshi Hata, Seiya Kikukawa, Miki Ebihara, Kazuki Kobayashi, Nozomi Kasakura, Takashi Kanamori, Tadaomi Furuta, Ai Kohata, Nobuaki Funahashi, Shota Matsumoto, Satoru Karasawa, Kazushi Kinbara, Naohiko Koshikawa, Hideya Yuasa","doi":"10.1002/ejoc.202500355","DOIUrl":"https://doi.org/10.1002/ejoc.202500355","url":null,"abstract":"By heating 1-(ω-azidoalkyl)-2-(2,2-dihalovinyl)arenes in DMF, intramolecular Huisgen cycloaddition between the azido group and the 1,1-dihalovinyl moiety proceeded smoothly to afford 5-halo-1,2,3-triazole-fused tricyclic benzocondensed compounds. Leveraging the remaining halogen groups, carbon-chain extension via Mizoroki–Heck or Suzuki–Miyaura coupling reactions, followed by an intramolecular Friedel–Crafts reaction, furnished polycyclic systems incorporating fused triazole rings. Furthermore, transformation of the halogen groups into 2-nitrobenzene derivatives via Suzuki–Miyaura cross-coupling, followed by a Cadogan reaction using triphenylphosphine, provided a series of fluorescent pentacyclic compounds.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"221 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-06-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144278652","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
Point‐to‐axis optical activity induction in extended, sterically congested chromophoric systems 扩展的、立体拥挤的显色系统中点对轴旋光性的诱导
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-06-13 DOI: 10.1002/ejoc.202500461
Marcin Kwit, Klaudia Chuchracka, Agnieszka Czapik, Paweł Skowronek
{"title":"Point‐to‐axis optical activity induction in extended, sterically congested chromophoric systems","authors":"Marcin Kwit, Klaudia Chuchracka, Agnieszka Czapik, Paweł Skowronek","doi":"10.1002/ejoc.202500461","DOIUrl":"https://doi.org/10.1002/ejoc.202500461","url":null,"abstract":"The readily available, modular and electronic circular dichroism (ECD)‐silent derivatives of terephthalaldehyde (the probes) have exhibited an induced optical activity upon condensation with chiral primary amines. The central unit of the probe serves as an amine binder by forming imine bonds and is flanked by two extended chromophoric units (“the wings”). Modification of the wings by diphenylamine or carbazole units affects the sterical and spectroscopic properties of the probes. An increase in sterical congestion within the probe core resulted in a change in the mechanism of optical activity induction. In the more congested systems, the point‐to‐axial chirality transmission from the chiral amine (the inducer) to the chromophoric system led to the adaptation of helical conformation by “the wings” and the appearance of non‐zero Cotton effects (CEs) in the low‐energy part of the ECD spectrum. However, the sterically congested probes were sensitive to the chirality of the inducers but relatively indifferent to the differences in their structure. Thus, the chirality of the inducers triggers conformational change towards the thermodynamically preferred conformational diastereoisomer due to the probe's —1 ‐ +1 operation scheme.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"37 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-06-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144288282","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
Selective Ruthenium‐Catalyzed Photoredox α‐C(sp3)–H Alkynylation of Cyclic Amines Under Visible Light 可见光下选择性钌催化环胺光氧化还原α - C(sp3) -H炔化反应
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-06-13 DOI: 10.1002/ejoc.202500254
Paulo Henrique Schneider, Caren D. G. Silva, Douglas B. Paixão, Eduardo G. O. Soares
{"title":"Selective Ruthenium‐Catalyzed Photoredox α‐C(sp3)–H Alkynylation of Cyclic Amines Under Visible Light","authors":"Paulo Henrique Schneider, Caren D. G. Silva, Douglas B. Paixão, Eduardo G. O. Soares","doi":"10.1002/ejoc.202500254","DOIUrl":"https://doi.org/10.1002/ejoc.202500254","url":null,"abstract":"A direct visible‐light α‐C(sp3)–H bond alkynylation of N‐aryl pyrrolidine derivatives with 1‐bromoalkynes has been developed, enabling the synthesis of propargylic amines. This transformation utilizes [Ru(bpy)3]Cl2·6H2O as a photocatalyst, driven by blue LED (455 nm) irradiation. Detailed mechanistic studies and cyclic voltammetry support the proposed reaction pathway, where the C(sp3)‐C(sp) bond formation occurs via the oxidation of α‐amino radicals, followed by a radical coupling with 1‐bromoalkynes. This approach offers a straightforward, efficient, and selective method for synthesizing a wide range of cyclic α‐aminoalkynes, yielding moderate to good yields.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"13 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-06-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144288283","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
首页 上一页 下一页 尾页
0
×
引用
GB/T 7714-2015
复制
MLA
复制
APA
复制
导出至
BibTeX EndNote RefMan NoteFirst NoteExpress
×
提示
您的信息不完整，为了账户安全，请先补充。
现在去补充
×
提示
您因"违规操作"
具体请查看互助需知
我知道了
×
提示
现在去查看 取消
×
提示
确定
请完成安全验证×
相关产品
×
本文献相关产品
联系我们：info@booksci.cn Book学术提供免费学术资源搜索服务，方便国内外学者检索中英文文献。致力于提供最便捷和优质的服务体验。 Copyright © 2023 布克学术 All rights reserved.
京ICP备2023020795号-1
ghs 京公网安备 11010802042870号
Book学术文献互助
Book学术文献互助群
群 号：604180095
Book学术官方微信