European Journal of Organic Chemistry最新文献_第2页

Ring Expansion of Carbocycles via Heteroatom‐Enabled Skeletal Editing 通过杂原子激活骨架编辑的碳环扩展

IF 2.8 3区化学

European Journal of Organic Chemistry Pub Date : 2026-11-09 DOI: 10.1002/ejoc.70960

Han Sun, Feiyue Zhang, Yi Wu, Albert S. C. Chan, Shan‐Shui Meng

{"title":"Ring Expansion of Carbocycles via Heteroatom‐Enabled Skeletal Editing","authors":"Han Sun, Feiyue Zhang, Yi Wu, Albert S. C. Chan, Shan‐Shui Meng","doi":"10.1002/ejoc.70960","DOIUrl":"https://doi.org/10.1002/ejoc.70960","url":null,"abstract":"Carbocycles serve as fundamental scaffolds in a wide range of biologically active molecules and functional materials. Traditional synthetic transformations predominantly target peripheral functional groups, while the emerging paradigm of skeletal editing enables direct remodeling of molecular carbon backbones. Among these strategies, heteroatom insertion has become a powerful approach to access high‐value heterocycles. In this review, we summarize recent progress (2020–2025) in ring expansion of carbocycles via nitrogen‐ and oxygen‐atom‐enabled skeletal editing, with an emphasis on the mechanistic paradigms of diverse strategies including transition‐metal catalysis, photochemical/electrochemical activation, radical relay cascades, and cation‐driven rearrangements. These methods enable selective incorporation of N or O atoms into inert C─C bonds, providing efficient access to diverse N ‐ and O ‐heterocycles. We also discuss the current challenges in this field, such as the development of general catalytic systems, expansion of unactivated substrate scope, and the lack of efficient insertion strategies for other heteroatoms, and provide an outlook on future development to offer insights for programmable skeletal editing and functional molecule design.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"7 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2026-11-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149374591","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

In Situ Generation of (Dichloroiodo)benzene From PhI(OAc) 2 and SOCl 2 : Application to the Synthesis of Chlorinated 1,3‐Dicarbonyl and Aromatic Compounds 由PhI(OAc) 2和SOCl 2原位生成（二氯碘）苯：在氯化1,3‐二羰基和芳香族化合物合成中的应用

IF 2.8 3区化学

European Journal of Organic Chemistry Pub Date : 2026-11-09 DOI: 10.1002/ejoc.70958

Junpei Matsuoka, Kumi Nakaoka, Haruhi Sato, Karin Izawa, Akira Nakamura, Tomohiro Maegawa

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Amphiphilic Dendrimers Based on a Thiacalix[4]arene‐Gallic Alcohol Conjugate: Synthesis, Aggregation Behavior, and Catalytic Activity in Aqueous Media 基于thacalix[4]芳烃-没食子醇共轭物的两亲性树状大分子：合成、聚集行为和在水介质中的催化活性

IF 2.8 3区化学

European Journal of Organic Chemistry Pub Date : 2026-11-09 DOI: 10.1002/ejoc.70957

Roman Gabdullin, Julia Abdullina, Artur Khannanov, Elza Sultanova, Vladimir Evtugyn, Svetlana Solovieva, Vladimir Burilov, Igor Antipin

{"title":"Amphiphilic Dendrimers Based on a Thiacalix[4]arene‐Gallic Alcohol Conjugate: Synthesis, Aggregation Behavior, and Catalytic Activity in Aqueous Media","authors":"Roman Gabdullin, Julia Abdullina, Artur Khannanov, Elza Sultanova, Vladimir Evtugyn, Svetlana Solovieva, Vladimir Burilov, Igor Antipin","doi":"10.1002/ejoc.70957","DOIUrl":"https://doi.org/10.1002/ejoc.70957","url":null,"abstract":"A novel family of amphiphilic dendrimers based on a thiacalix[4]arene‐gallic alcohol conjugate was synthesized via Mitsunobu reaction followed by copper‐catalyzed azide–alkyne cycloaddition (CuAAC). Three types of polar peripheral groups—sulfonate (SO 3 Na), oligoethylene glycol (EG), and hydroxyl (OH)—were introduced to impart hydrophilic character, while the hydrophobic thiacalix[4]arene core served as the lipophilic domain. The dendrimers were employed as stabilizers for palladium nanoparticles (Pd NPs). Nanoparticle racking analysis revealed that the terminal group critically governs aggregation behavior, with SO 3 Na inducing compaction, EG promoting surface aggregation, and OH disrupting pre‐existing aggregates to generate a larger number of smaller particles. The Pd&R‐TCA composites exhibited excellent catalytic activity in the reduction of p ‐nitrophenol ( k app up to 0.9 min −1 ) and p ‐ethylnitrobenzene ( k app up to 0.6 min −1 ), significantly outperforming unsupported Pd 0 and Pd(OAc) 2 . In aqueous Suzuki–Miyaura and Heck cross‐coupling, the Pd&EG‐TCA system demonstrated the highest conversions (up to 99%) due to its superior thermal stability and substrate solubilization capacity, as confirmed by TEM and Orange OT tests. The activity order reversed compared with reduction reactions, highlighting that the optimal dendrimer stabilizer depends on both reaction type and substrate hydrophobicity.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"17 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2026-11-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149374599","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

Trifluoromethanesulfonyl‐Based Reagents: Novel Synthetic Strategies and Mechanistic Insights for Trifluoromethylation Transformations 基于三氟甲烷磺酰的试剂：三氟甲基化转化的新合成策略和机理见解

IF 2.8 3区化学

European Journal of Organic Chemistry Pub Date : 2026-11-09 DOI: 10.1002/ejoc.70945

Jia‐Le Niu, Jia‐Lin Zhan, Zhou Sun, Chao‐Peng Yang, Ya‐Ping Han, Yong‐Min Liang

{"title":"Trifluoromethanesulfonyl‐Based Reagents: Novel Synthetic Strategies and Mechanistic Insights for Trifluoromethylation Transformations","authors":"Jia‐Le Niu, Jia‐Lin Zhan, Zhou Sun, Chao‐Peng Yang, Ya‐Ping Han, Yong‐Min Liang","doi":"10.1002/ejoc.70945","DOIUrl":"https://doi.org/10.1002/ejoc.70945","url":null,"abstract":"Trifluoromethylated compounds act as indispensable synthetic building blocks in the fields of agrochemicals, pharmaceuticals, and functional materials, by virtue of their tunable lipophilicity, enhanced cell membrane permeability and superior metabolic stability. The distinctive physicochemical characteristics of the trifluoromethyl group have stimulated tremendous research interest in developing efficient, site‐selective, and scalable synthetic methodologies for the trifluoromethylation of diverse organic molecular skeletons. Over recent years, trifluoromethanesulfonyl‐derived trifluoromethylating reagents have arisen as versatile, bench‐stable, and easily accessible CF 3 sources, facilitating the development of numerous green, atom‐economic, and mild synthetic strategies to access structurally varied trifluoromethylated compounds and functional molecular scaffolds. This review systematically summarizes the advances in catalytic trifluoromethylation reactions enabled by trifluoromethanesulfonyl derivatives, which are categorized into four main types: photoredox catalysis, electrochemical catalysis, metal‐free catalysis, and transition‐metal catalysis for trifluoromethylation transformations.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"68 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2026-11-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149374601","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

Photocatalytic Pyridylation of Cyanopyridines With Benzyl and Alkyl Dihydropyridines: Divergent Reactivity and Mechanistic Insights 光催化苄基和烷基二氢吡啶对氰吡啶的吡啶化反应：不同的反应活性和机理

IF 2.8 3区化学

European Journal of Organic Chemistry Pub Date : 2026-11-09 DOI: 10.1002/ejoc.70931

Ziming Li, Zhiqin Zhang, Jiaxi Xu, Ning Chen

引用次数: 0

Cyanation of Dihydropyrrolo[2,1‐ a ]isoquinoline With Phenylacetonitrile 二氢吡咯[2,1‐a]异喹啉与苯乙腈的氰化反应

IF 2.8 3区化学

European Journal of Organic Chemistry Pub Date : 2026-11-09 DOI: 10.1002/ejoc.70967

Dianming Chen, Wei Lv, Zhikang Lv, Chao Liu, Shuo Yuan, Yuehai Shen, Jian Li

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One‐Pot Metal‐Free Synthesis of 3‐Substituted 4‐Hydroxyisocoumarins via Oxa‐Hauser–Kraus Reaction of Sulfonyl Phthalide With Glyoxal Derivatives 磺酰酞与乙二醛衍生物的Oxa - Hauser-Kraus反应一锅无金属合成3 -取代4 -羟基异香豆素

IF 2.8 3区化学

European Journal of Organic Chemistry Pub Date : 2026-11-09 DOI: 10.1002/ejoc.70944

Rajni Kumari, Abhishek R. Tiwari, Shyam Sreedhar, Irishi N. N. Namboothiri

引用次数: 0

Photochemical CF 3 Radical Generation: A Spin Trapping/Electron Paramagnetic Resonance and In Situ 19 F Nuclear Magnetic Resonance Study 光化学cf3自由基的产生：自旋捕获/电子顺磁共振和原位核磁共振研究

IF 2.8 3区化学

European Journal of Organic Chemistry Pub Date : 2026-11-09 DOI: 10.1002/ejoc.70885

Béatrice Tuccio, Flavien Bourdreux, Guillaume Dagousset, Géraldine Masson, Emmanuel Magnier, Elsa Anselmi

{"title":"Photochemical CF 3 Radical Generation: A Spin Trapping/Electron Paramagnetic Resonance and In Situ 19 F Nuclear Magnetic Resonance Study","authors":"Béatrice Tuccio, Flavien Bourdreux, Guillaume Dagousset, Géraldine Masson, Emmanuel Magnier, Elsa Anselmi","doi":"10.1002/ejoc.70885","DOIUrl":"https://doi.org/10.1002/ejoc.70885","url":null,"abstract":"Trifluoromethyl (CF 3 ) radicals, generated under photoredox catalysis, are valuable tools for introducing CF 3 groups into organic molecules, significantly altering their physical, chemical, and biological properties. Although reagents, like the Umemoto and Togni compounds, are widely used to introduce CF 3 groups, the details of how they generate CF 3 radicals are not well understood. In this article, we study the reactivity of 18 different CF 3 ‐donating reagents using two methods: spin trapping‐electron paramagnetic resonance (ST/EPR) spectroscopy and in situ 19 F nuclear magnetic resonance (NMR). ST/EPR measures how quickly CF 3 radicals are released by detecting their reaction with the spin trap 2‐methyl‐2‐nitrosopropane (MNP), forming MNP‐CF 3 adducts. In parallel, 19 F NMR monitors how the reagents are consumed and which products are formed during trifluoromethylation of alkenes. Notably, the observed reactivity trends differ between the two techniques, likely due to differences in reaction environments and side reactions such as CF 3 I formation. The comparison between each reagent must therefore be limited to the values determined by each analytical technique, EPR or NMR. This study provides nevertheless new insights into how CF 3 radicals are generated and how the structure of the reagent influences its reactivity.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"14 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2026-11-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149374593","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

Strategic Formation of Indoles Using Phenyl Hydrazine as a Key Reagent 以苯肼为关键试剂的吲哚合成研究

IF 2.8 3区化学

European Journal of Organic Chemistry Pub Date : 2026-11-06 Epub Date: 2026-09-30 DOI: 10.1002/ejoc.70878

Amit Kumar Verma, Anuj Yadav, Devendra Singh Negi, Surendra Puri

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Copper-Catalyzed One-Pot Approach to 6-Membered Sultams From Vinyl Sulfonamide Using Methanol as C1 Building Block 以甲醇为C1构建块，铜催化一锅法从乙烯基磺胺中提取6元磺胺

IF 2.8 3区化学

European Journal of Organic Chemistry Pub Date : 2026-11-06 Epub Date: 2026-10-01 DOI: 10.1002/ejoc.70889

Sichun Ai, Xuan Wang, Ruijun Wei, Chenrui Niu, Bo Lv, Yanjie Wang, Min Wang

引用次数: 0