European Journal of Organic Chemistry最新文献_第3页

Heavy Atom‐Enhanced Photooxidation Performance of Carbazole‐Substituted BODIPY Dyes 重原子增强咔唑取代的BODIPY染料的光氧化性能

IF 2.8 3区化学

European Journal of Organic Chemistry Pub Date : 2025-09-30 DOI: 10.1002/ejoc.202500797

Mücahit Özdemir, Esra Sevimli, Gülsema Ozan, Ümit Salan, Bahattin Yalçın, Baybars Köksoy

{"title":"Heavy Atom‐Enhanced Photooxidation Performance of Carbazole‐Substituted BODIPY Dyes","authors":"Mücahit Özdemir, Esra Sevimli, Gülsema Ozan, Ümit Salan, Bahattin Yalçın, Baybars Köksoy","doi":"10.1002/ejoc.202500797","DOIUrl":"https://doi.org/10.1002/ejoc.202500797","url":null,"abstract":"In this study, halogenated BODIPYs (C‐Br2‐BDPY and C‐I2‐BDPY) bearing a carbazole group at the meso position are synthesized and characterized using various spectroscopic techniques. Single‐crystal X‐ray diffraction analysis of the C‐I2‐BDPY revealed that it crystallizes in a triclinic crystal system with a P‐1 space group. The optical properties, singlet oxygen generation capacities, and photocatalytic activities of the BODIPY derivatives are evaluated with respect to juglone synthesis. While the nonhalogenated BODIPY (C‐BDPY) exhibit negligible singlet oxygen generation (ΦΔ < 0.05), the iodinated (C‐I2‐BDPY) and brominated (C‐Br2‐BDPY) derivatives demonstrate considerably higher singlet oxygen quantum yields of 0.82 and 0.73, respectively. In the photooxidation reaction of 1,5‐dihydroxynaphthalene (DHN) to juglone, these halogenated BODIPY compounds achieve conversion yields of 62.6% for C‐Br2‐BDPY and 87.8% for C‐I2‐BDPY within one hour. The turnover number values of the BODIPY photosensitizers show a continuous increase over time, indicating sustained product formation, whereas the turnover frequency values gradually decline, reflecting the decrease in reaction rate as the process progress. Density functional theory calculations support the experimental results by demonstrating that the presence of heavy atoms facilitates intersystem crossing and enhances the thermodynamic feasibility of the photooxidation reactions.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"29 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-09-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145194972","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

Efficient Hydrosilylation Reaction of Olefins Catalyzed by a Dinuclear Ruthenium Complex 双核钌配合物催化烯烃高效硅氢化反应

IF 2.7 3区化学

European Journal of Organic Chemistry Pub Date : 2025-09-29 DOI: 10.1002/ejoc.202500578

Fei Xie , Sheng Zhang , Xiujuan Feng , Xiaoqiang Yu , Ming Bao

引用次数: 0

Exploring the Regioselectivity of Diels–Alder Reactions of 2,6‐Disubstituted Benzoquinones through DFT Calculations 通过DFT计算探索2,6 -二取代苯醌Diels-Alder反应的区域选择性

IF 2.8 3区化学

European Journal of Organic Chemistry Pub Date : 2025-09-29 DOI: 10.1002/ejoc.202500661

Erik Kalla, Hugo Semrád, Lukáš Maier, Kamil Paruch, Hendrik Zipse, Markéta Munzarová

{"title":"Exploring the Regioselectivity of Diels–Alder Reactions of 2,6‐Disubstituted Benzoquinones through DFT Calculations","authors":"Erik Kalla, Hugo Semrád, Lukáš Maier, Kamil Paruch, Hendrik Zipse, Markéta Munzarová","doi":"10.1002/ejoc.202500661","DOIUrl":"https://doi.org/10.1002/ejoc.202500661","url":null,"abstract":"Diels–Alder reactions of 2‐methyl‐6‐substituted‐p‐benzoquinones are studied using quantum chemical calculations. The effect of 19 substituents, including halomethyl, alkyl, vinyl, ethynyl, nitrile, trifluoromethyl, methoxy, cyclohexenyl, phenyl, and trifluoromethoxyphenyl groups, on the reaction barriers is explored by the B3LYP‐D3, M06‐2X, and DLPNO‐CCSD(T) methods. Gibbs free activation energies are compared for the two regioisomeric products experimentally observed in the reaction mixture. For 75% of the substituents, the calculated barrier difference (ΔG‡b – ΔG‡a) lies within 2.0 kcal mol−1 of the value determined from the experimentally observed product ratio a/b. Activation barriers are further analyzed in terms of the underlying deformation and interaction energies. The difference in deformation energies of transition states corresponding to the two regioisomers ranges from −8.0 to +8.0 kcal mol−1 and is directly proportional to experimental ln(a/b) values. Differences in interaction energies between regioisomeric transition states are, in comparison, significantly smaller.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"118 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-09-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145182759","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

Copper Coils as Efficient and Inexpensive Reactors for the Synthesis of Tetrazoles in Flow Chemistry 流动化学中铜圈作为高效、廉价的四氮唑合成反应器

IF 2.7 3区化学

European Journal of Organic Chemistry Pub Date : 2025-09-29 DOI: 10.1002/ejoc.202500774

Maite Molins , Natàlia Roig , Javier Fernandez‐Garcia , Xavier Berzosa

{"title":"Copper Coils as Efficient and Inexpensive Reactors for the Synthesis of Tetrazoles in Flow Chemistry","authors":"Maite Molins , Natàlia Roig , Javier Fernandez‐Garcia , Xavier Berzosa","doi":"10.1002/ejoc.202500774","DOIUrl":"10.1002/ejoc.202500774","url":null,"abstract":"<div><div>Sartans are an important family of drugs used to treat hypertension. A common characteristic of most of them is a biphenyl moiety with a tetrazole ring in the <em>ortho</em> position of the phenyl–phenyl bond. This tetrazole is typically synthesized from the respective nitriles through a [3 + 2] azide‐nitrile cycloaddition. However, the use of large amounts of azides at high temperatures for extended periods of time is inherently concerning, as serious accidents can occur if safety protocols are not thoroughly developed and implemented. The implementation of these procedures in continuous flow would therefore be beneficial from the safety perspective. In this article, a method is presented for the preparation of tetrazoles from the respective nitriles employing a copper coil as reactor and catalyst. The reaction parameters have been studied and optimized to maximize conversion. A variety of benzonitriles with different ring substituents have been transformed in moderate to good yields and copper leaching has been analyzed, showing that the copper leached is enough to catalyze this reaction. More interestingly, the method has been applied to obtain the tetrazole ring present in a key intermediate used in sartan manufacturing, a highly sterically hindered compound.</div></div>","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"28 36","pages":"Article e202500774"},"PeriodicalIF":2.7,"publicationDate":"2025-09-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145195792","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

A Fullerene‐Based Selenosugar Ball 基于富勒烯的硒糖球

IF 2.7 3区化学

European Journal of Organic Chemistry Pub Date : 2025-09-29 DOI: 10.1002/ejoc.202500557

Reinier Lemos , Yoana Pérez‐Badell , Mauro De Nisco , Giovanna Cimmino , Claudia González , Andrea Carpentieri , Severina Pacifico , Margarita Suárez , Silvana Pedatella

{"title":"A Fullerene‐Based Selenosugar Ball","authors":"Reinier Lemos , Yoana Pérez‐Badell , Mauro De Nisco , Giovanna Cimmino , Claudia González , Andrea Carpentieri , Severina Pacifico , Margarita Suárez , Silvana Pedatella","doi":"10.1002/ejoc.202500557","DOIUrl":"10.1002/ejoc.202500557","url":null,"abstract":"<div><div>Fullerenes functionalized with selenosugar moieties are of particular interest because of their important properties, as one fragment enhances the properties of the other. Selenosugars are not only solubilizing groups, but their intrinsic biological properties also provide additional attractive features to the conjugates. Here the synthesis is reported of a fullerene hexakis‐adduct decorated with 12 peripheral seleno‐<span>d</span>‐talitol moieties with a <em>T</em><sub><em>h</em></sub>‐symmetric structure, which can be efficiently synthesized from the hexakis‐adduct of [60]fullerene prepared via a cycloaddition reaction and subsequent copper‐catalyzed azide‐alkyne cycloaddition click chemistry. This large‐scale system, refer to as the selenosugar ball (SeB), has been characterized by <sup>1</sup>H NMR and <sup>13</sup>C NMR spectroscopy, mass spectrometry, UV‐spectroscopy, and dynamic light scattering (DLS). Theoretical calculations using the multilevel DFT‐B3LYP‐D3(BJ)/6–311 G(2 d,p)//PM7 methodology are performed to predict the most stable conformation for the compound and to determine the factors that control the geometry of this molecule. In addition, some physicochemical parameters are estimated. Also, this new compound is tested on human keratinocyte HaCaT cells to determine its cytotoxicity and potential applications.</div></div>","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"28 36","pages":"Article e202500557"},"PeriodicalIF":2.7,"publicationDate":"2025-09-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145195793","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 Chiroptical Property of Chiral Heteroatom‐Embedded Zigzag‐Type Hydrocarbon Belts 手性杂原子嵌入之字形烃带的合成及其手性研究

IF 2.7 3区化学

European Journal of Organic Chemistry Pub Date : 2025-09-29 DOI: 10.1002/ejoc.202500755

Zi‐Yue Jin , Mei‐Xiang Wang , Shuo Tong

引用次数: 0

Cellulose‐Based Nanosponges Loaded with Palladium as Efficient Heterogeneous Catalysts for the Synthesis of Challenging Derivatives with Pharmaceutical Relevance 负载钯的纤维素基纳米海绵作为高效非均相催化剂用于合成具有药物相关性的具有挑战性的衍生物

IF 2.7 3区化学

European Journal of Organic Chemistry Pub Date : 2025-09-29 DOI: 10.1002/ejoc.202500517

Giulia Cazzaniga , Gloria Nicastro , Carlo Punta , Alessandro Sacchetti , Stefania Villa , Matteo Mori , Laura Riva

{"title":"Cellulose‐Based Nanosponges Loaded with Palladium as Efficient Heterogeneous Catalysts for the Synthesis of Challenging Derivatives with Pharmaceutical Relevance","authors":"Giulia Cazzaniga , Gloria Nicastro , Carlo Punta , Alessandro Sacchetti , Stefania Villa , Matteo Mori , Laura Riva","doi":"10.1002/ejoc.202500517","DOIUrl":"10.1002/ejoc.202500517","url":null,"abstract":"<div><div>Developing efficient catalytic systems is crucial for synthesizing complex heterocyclic compounds used in pharmaceuticals. However, key motifs, like pyridine and furan derivatives, pose challenges due to regioselectivity and sensitivity to harsh conditions. Conventional homogeneous palladium‐catalyzed cross‐coupling reactions, while effective, suffer from catalyst recovery issues, palladium contamination, and environmental concerns. To overcome these limitations, this study explores cellulose‐based nanosponges as sustainable palladium supports for heterogeneous catalysis, enhancing stability and green chemistry integration. These nanostructured materials, synthesized from cellulose, provide a high‐surface‐area scaffold that enhances uniform palladium dispersion, with a 22% w/w overall loading measured using inductively coupled plasma optical emission spectroscopy, and prevents metal leaching, integrating green chemistry principles and a safe‐and‐sustainable‐by‐design approach. In this work, the optimization of Suzuki–Miyaura couplings using CNS‐Pd under mild conditions, showcasing the efficiency and selectivity of this heterogeneous catalyst in the synthesis of pharmaceutically relevant heterocyclic derivatives, is presented. Notably, high reaction yields (65%–99%) even with unstable boronic derivatives are achieved, which are typically synthesized using homogeneous catalysts, often with poor yields, selectivity and purity of the final products. The obtained results underscore the potential of biopolymer‐based catalysts to drive innovation in sustainable pharmaceutical synthesis, effectively bridging the gap between heterogeneous catalysis and pharmaceutical chemistry.</div></div>","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"28 36","pages":"Article e202500517"},"PeriodicalIF":2.7,"publicationDate":"2025-09-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145195791","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

Pd‐Catalyzed Synthesis of Arylacetyl Thioesters from Benzyl Chlorides and Thioformates 钯催化氯苄和硫甲酸酯合成芳基乙酰硫酯

IF 2.7 3区化学

European Journal of Organic Chemistry Pub Date : 2025-09-29 DOI: 10.1002/ejoc.202500752

Anhui Wei , Ruiyun Wang , Nanchun Liu , Yicheng Wang , Bao Gao

引用次数: 0

Front Cover: Employing Multicomponent Reactions in Heterocycle Synthesis: Recent Advances (Eur. J. Org. Chem. 35/2025) 封面：多组分反应在杂环合成中的应用：最新进展。j . Org。化学35/2025)

IF 2.7 3区化学

European Journal of Organic Chemistry Pub Date : 2025-09-28 DOI: 10.1002/ejoc.70137

Tapas Ghosh, Sk Shamim Ahamed, Rahul Paul, Paramita Saha

引用次数: 0

Stitching β-Ketothioamides with N-Tosylbenzoquinone Imine: Transition-Metal Free Site-Selective Domino Synthesis of 2-Amino-3-aroyl-5-sulfonamide Substituted Benzo[b]furans β-酮硫酰胺与n-甲苯苯醌亚胺的拼接：2-氨基-3-芳基-5-磺酰胺取代苯并[b]呋喃的无过渡金属选择性多米诺合成

IF 2.8 3区化学

European Journal of Organic Chemistry Pub Date : 2025-09-28 DOI: 10.1002/ejoc.202500675

Vimlesh Kumar Kanaujiya, Nimisha Gupta, Virendra Prasad, Maya Shankar Singh

{"title":"Stitching β-Ketothioamides with N-Tosylbenzoquinone Imine: Transition-Metal Free Site-Selective Domino Synthesis of 2-Amino-3-aroyl-5-sulfonamide Substituted Benzo[b]furans","authors":"Vimlesh Kumar Kanaujiya, Nimisha Gupta, Virendra Prasad, Maya Shankar Singh","doi":"10.1002/ejoc.202500675","DOIUrl":"https://doi.org/10.1002/ejoc.202500675","url":null,"abstract":"Benzofuran derivatives are core components in many biologically active natural and synthetic compounds including approved drugs. Herein, an easy-to-access and TM-free, one-pot, three-step synthesis of 2-amino-3-aroyl-5-sulfonamide substituted benzo[<i>b</i>]furans bearing many functional groups of different electronic and steric nature using thioamides (as a 2C synthon) and <i>N</i>-tosylbenzoquinone imine (as a CCO unit partner) at room temperature in open air is presented for the first time. The reaction proceeds via deprotonation/Michael addition/cyclization/aromatization cascades forming two new (C<span></span>C and C<span></span>O) bonds and one ring, liberating only H<sub>2</sub>S as a byproduct. High resolution mass spectrometry study endorses the key intermediates involved during reaction, validating excellent regio- and chemoselectivity. This protocol will not only provide an efficient and scalable method to access diverse benzo[<i>b</i>]furans that could be adaptable to late-stage functionalization but also enrich the research domain of thioamides.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"199 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-09-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145183092","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