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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
Kinetic Estimation of Ring Opening of Cyclopropylvinyl Radical Using Radical Substitution Reaction on at the Tin Atom 用锡原子上的自由基取代反应估计环丙基乙烯自由基开环的动力学
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-06-13 DOI: 10.1002/ejoc.202500225
Akio Kamimura, Kanako Ishido
{"title":"Kinetic Estimation of Ring Opening of Cyclopropylvinyl Radical Using Radical Substitution Reaction on at the Tin Atom","authors":"Akio Kamimura, Kanako Ishido","doi":"10.1002/ejoc.202500225","DOIUrl":"https://doi.org/10.1002/ejoc.202500225","url":null,"abstract":"The present study investigated kinetic estimation of cyclopropylvinyl radical. Treatment of cyclopropane‐substituted 1,6‐enyne with Bu3SnH resulted in multi‐component radical cascade reaction, which commenced with addition of Bu3Sn radical to unsaturated amide followed by 5‐exo‐radical cyclization, generating cyclopropylvinyl radical intermediate. The intermediate then underwent either the ring cleavage of the adjacent cyclopropane ring, yielding the allene product, or the formation of dihydrostannole which was formed through direct radical substitution on a tin atom. The reaction path depended on the concentration of Bu3SnH. We applied this cascade process for a mechanistic probe to explore the radical reaction, and estimated kinetic parameters of the ring cleavage of the cyclopropylvinyl radical, which has not been well investigated.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"151 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-06-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144278289","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
Reaction of Nitrones with Phosphinylallenes: DFT Mechanistic Investigations 硝基酮与膦烯的反应：DFT机理研究
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-06-12 DOI: 10.1002/ejoc.202500359
Rayhane Hammami, Pascale Maldivi, Sébastien Carret, Soufiane Touil, Jean-François Poisson, Benjamin DARSES
{"title":"Reaction of Nitrones with Phosphinylallenes: DFT Mechanistic Investigations","authors":"Rayhane Hammami, Pascale Maldivi, Sébastien Carret, Soufiane Touil, Jean-François Poisson, Benjamin DARSES","doi":"10.1002/ejoc.202500359","DOIUrl":"https://doi.org/10.1002/ejoc.202500359","url":null,"abstract":"The reaction between phosphinylallenes and nitrones efficiently leads to 4-phosphinylpyrrolidin-3-ones. The mechanism involved in this reaction was theoretically studied to understand the overall pathway and the stereochemical outcome of the transformation. The first step of the mechanism is a (3+2) cycloaddition between the nitrone and the allene delivering an isoxazolidine ylidene intermediate. This never isolated intermediate undergoes a spontaneous rearrangement to the final 4-phosphinylpyrrolidin-3-one through the homolytic N–O bond cleavage followed by rotation and C–N recombination of the biradical intermediate. The computational results obtained from this study are highly informative for potentially obtaining diastereoisomerically and enantiomerically pure 4-phosphinylpyrrolidin-3-ones by a judicious choice of substituents on nitrone and allene.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"602 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-06-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144269437","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: Silver-Mediated Cascade Synthesis of Open-Cage Fullerenes from C60 and Propargylic Carbonates (Eur. J. Org. Chem. 22/2025) 前封面：银介导的由C60和丙炔碳酸酯级联合成开笼富勒烯。j . Org。化学22/2025)
IF 2.5 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-06-12 DOI: 10.1002/ejoc.202582201
Michio Yamada, Masahiro Miyazaki, Hiro Yamazaki, Miyu Kaneko, Yoshihisa Hashimoto, Yutaka Maeda
{"title":"Front Cover: Silver-Mediated Cascade Synthesis of Open-Cage Fullerenes from C60 and Propargylic Carbonates (Eur. J. Org. Chem. 22/2025)","authors":"Michio Yamada,&nbsp;Masahiro Miyazaki,&nbsp;Hiro Yamazaki,&nbsp;Miyu Kaneko,&nbsp;Yoshihisa Hashimoto,&nbsp;Yutaka Maeda","doi":"10.1002/ejoc.202582201","DOIUrl":"https://doi.org/10.1002/ejoc.202582201","url":null,"abstract":"<p><b>The Front Cover</b> shows the molecular structure of an open-cage fullerene synthesized according to a recently developed silver-mediated cascade synthetic methodology. The proposed protocol facilitates the synthesis of bisfulleroid derivatives, wherein a hydrogen atom resides on one side of the bridgehead carbon at the orifice, while an aryl or alkyl substituent is strategically introduced on the opposite side. More information can be found in the Research Article by M. Yamada and co-workers (DOI: 10.1002/ejoc.202500114).\u0000 <figure>\u0000 <div><picture>\u0000 <source></source></picture><p></p>\u0000 </div>\u0000 </figure></p>","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"28 22","pages":""},"PeriodicalIF":2.5,"publicationDate":"2025-06-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/ejoc.202582201","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144273284","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
Identifying the True Catalyst: A Mn(II) Salt versus Mn(II) Complexes in Epoxidation with m-Chloroperbenzoic Acid 确定Mn（II）盐与Mn（II）配合物在间氯过苯甲酸环氧化反应中的真正催化剂
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-06-12 DOI: 10.1002/ejoc.202500432
Milica Savić, Aleksandra Mitrović, Božidar Čobeljić, Andrej Pevec, Matija Zlatar, Maja Gruden, Wesley R. Browne, Marika Di Berto Mancini
{"title":"Identifying the True Catalyst: A Mn(II) Salt versus Mn(II) Complexes in Epoxidation with m-Chloroperbenzoic Acid","authors":"Milica Savić, Aleksandra Mitrović, Božidar Čobeljić, Andrej Pevec, Matija Zlatar, Maja Gruden, Wesley R. Browne, Marika Di Berto Mancini","doi":"10.1002/ejoc.202500432","DOIUrl":"https://doi.org/10.1002/ejoc.202500432","url":null,"abstract":"The oxidant meta-chloroperbenzoic acid (m-CPBA) is used widely for the epoxidation of alkenes, yet its efficiency is often limited under ambient conditions. In this study we investigate the catalytic activity of a Mn(II) salt and mononuclear Mn(II) complexes, two of which are reported here for the first time, in the epoxidation of alkenes with m-CPBA under ambient conditions. Time-resolved Raman spectroscopy was used to monitor substrate conversion, oxidant consumption, and product formation. The data reveal that simple Mn(II) salts exhibit significantly higher catalytic activity than Mn(II) complexes, indicating that ligand coordination inhibits the reactivity of the manganese centre. The catalytic efficiency of Mn(II) perchlorate was particularly notable, achieving near-complete oxidation of styrene within minutes under mild conditions. Furthermore, epoxidation of a range of alkenes demonstrated that Mn(II) salts provide broad substrate scope and high selectivity. These findings suggest that simple Mn(II) salts can serve as highly efficient and cost-effective catalysts in alkene epoxidations with m-CPBA.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"42 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-06-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144269434","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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