European Journal of Organic Chemistry最新文献_第9页

Synthesis of Indole‐Fused Chromane‐Based Spirooxindoles via Brønsted Acid‐Catalyzed Regioselective [5+1] Annulation Brønsted酸催化区域选择性[5+1]环法制备吲哚-铬基螺旋菌吲哚

IF 2.5 3区化学

European Journal of Organic Chemistry Pub Date : 2025-04-01 DOI: 10.1002/ejoc.202401405

Le‐Hua Ye , Xiao Cheng , Zi‐Qi Zhu , Prof. Feng Shi

引用次数: 0

Structure‐Property Evaluation of Knoevenagel‐Derived π‐Conjugated Organic Systems knoevenagel衍生π共轭有机体系的结构-性能评价

IF 2.5 3区化学

European Journal of Organic Chemistry Pub Date : 2025-04-01 DOI: 10.1002/ejoc.202401367

Maruti Vibhuti Ravikumar , Aswani K Raj , Malakalapalli Rajeswara Rao , Vellanki Lakshmi

引用次数: 0

NaI‐Promoted Synthesis of Dihydroquinolines via an Unusual Azetine Intermediate NaI促进了一种不寻常的Azetine中间体合成二氢喹啉

IF 2.5 3区化学

European Journal of Organic Chemistry Pub Date : 2025-04-01 DOI: 10.1002/ejoc.202401415

Futong Li , Dr. Zhongxuan Qiu , Prof. Daoshan Yang , Prof. Longjiang Huang , Dr. Feifei Xin

引用次数: 0

Unraveling Phenanthrenoid Dimerization in Juncus acutus: A DFT‐Guided Exploration of Radical‐Coupling Reaction Mechanisms 尖茎中类菲二聚化的揭示：DFT引导下自由基偶联反应机制的探索

IF 2.5 3区化学

European Journal of Organic Chemistry Pub Date : 2025-04-01 DOI: 10.1002/ejoc.202401123

Dr. Federico Coppola , Prof. Paola Cimino , Prof. Nadia Rega , Dr. Simona Zuppolini , Prof. Giovanni Di Fabio , Prof. Armando Zarrelli

{"title":"Unraveling Phenanthrenoid Dimerization in Juncus acutus: A DFT‐Guided Exploration of Radical‐Coupling Reaction Mechanisms","authors":"Dr. Federico Coppola , Prof. Paola Cimino , Prof. Nadia Rega , Dr. Simona Zuppolini , Prof. Giovanni Di Fabio , Prof. Armando Zarrelli","doi":"10.1002/ejoc.202401123","DOIUrl":"10.1002/ejoc.202401123","url":null,"abstract":"<div><div><em>Juncus acutus</em> is a plant found near ponds and brackish marshes, producing secondary metabolites like phenanthrenoid dimers with antibacterial, antioxidant, and anti‐inflammatory activities. Despite this, little is known about the detailed mechanisms behind their dimerization reactions. In this study, we used Density Functional Theory to explore the reaction mechanisms of phenanthrene and dihydrophenanthrene species in radical coupling, both in gas‐phase and in solution. The dimerization reactions, initiated by the OH radical, result in the formation of two phenanthrenoid dimers (homodimer and heterodimer). The OH radical abstracts a hydrogen atom from the hydroxyl group, leading to the formation of radicals and water. Our analysis of electronic spin density highlighted the preferred reactive sites that drive regioselective dimer formation. Furthermore, the study identifies a triplet <em>π</em>‐<em>π</em> stacked intermediate preceding the diketone formation on the singlet potential energy surface, revealing a two‐state reactivity mechanism. The diketone dimers are then converted via a water‐mediated keto‐enol tautomerization into their dienolic forms, completing the reaction pathway. This work offers insights into the complex dimerization processes of phenanthrenoids in nature, using computational methods to shed light on poorly understood molecular mechanisms in plant organisms.</div></div>","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"28 13","pages":"Article e202401123"},"PeriodicalIF":2.5,"publicationDate":"2025-04-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/ejoc.202401123","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142880099","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

Regio‐ and Stereo‐Selective Ring Opening of Cyclopropenes with Triflic Acid: en Route to Vinyl Triflates 环丙烯与三氟酸的区域和立体选择性开环：制备三氟乙烯酯的过程

IF 2.5 3区化学

European Journal of Organic Chemistry Pub Date : 2025-04-01 DOI: 10.1002/ejoc.202401410

Shu‐Ya Xin , Qian Wang , Fei Wang

引用次数: 0

High Throughput Experimentation as a Tool to Guide the Microwave Assisted Catalytic Amidation of Aryl Amines with Aryl Acids 高通量实验作为指导微波辅助芳基胺与芳基酸酰胺化的工具

IF 2.5 3区化学

European Journal of Organic Chemistry Pub Date : 2025-04-01 DOI: 10.1002/ejoc.202400764

Giulia Murbach , Shruti A. Biyani , David H. Thompson

{"title":"High Throughput Experimentation as a Tool to Guide the Microwave Assisted Catalytic Amidation of Aryl Amines with Aryl Acids","authors":"Giulia Murbach , Shruti A. Biyani , David H. Thompson","doi":"10.1002/ejoc.202400764","DOIUrl":"10.1002/ejoc.202400764","url":null,"abstract":"<div><div>The formation of amides is one of the most essential transformations in the pharmaceutical industry, but most synthetic procedures include the use of stoichiometric poor atom economy reagents. These limitations are often compounded when condensing aryl amines with aryl acids due to their inherently low reactivity. To overcome such hurdles, we utilized high throughput experimentation to screen 640 different reaction conditions to find a suitable catalyst and solvent for benzamide formation. Based on those initial findings, we developed an efficient catalytic transformation of aryl amines with aryl acids into N‐arylbenzamides using a 15 mol % loading of 2,4‐bis(trifluoromethyl) phenyl boronic acid and trimethylamine N‐oxide in 2‐MeTHF under microwave conditions for 1 h in the presence of 3 Å molecular sieves. Our method shows that even sterically hindered amines and carboxylic acids can be converted to the corresponding N‐arylbenzamides, including previously reported unreactive aromatic and secondary amines, in good to excellent yields. This approach follows the principles of green chemistry through use of<sup>[1]</sup> catalysis to improve atom economy,<sup>[2]</sup> a biorenewable solvent (2‐MeTHF),<sup>[3]</sup> high substrate loadings (0.5 M), and<sup>[4]</sup> energy efficient microwave heating.</div></div>","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"28 13","pages":"Article e202400764"},"PeriodicalIF":2.5,"publicationDate":"2025-04-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/ejoc.202400764","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143666404","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

Transition‐Metal Catalyzed, Thermally Driven [2π+2π]‐Cycloadditions of Olefins and Alkynes 过渡金属催化，热驱动[2π+2π]-烯烃和炔的环加成

IF 2.5 3区化学

European Journal of Organic Chemistry Pub Date : 2025-04-01 DOI: 10.1002/ejoc.202401403

M.Sc. Leif E. Hertwig , M.Sc. Felix J. Becker , Priv.Doz. Dragoş‐Adrian Roşca

引用次数: 0

Multianalytical Characterization of Acrylic Industrial Paints Used in Contemporary Mural Art 当代壁画艺术中丙烯酸工业颜料的多分析表征

IF 2.8 3区化学

European Journal of Organic Chemistry Pub Date : 2025-04-01 DOI: 10.1002/ejoc.202400759

Andrea Poliszuk, Laura Gelabert, Gabriel O. Ybarra, Marta S. Maier

引用次数: 0

Acceptor‐Donor‐Acceptor Systems Based on Indacenodithiophene‐Extended Tetrathiafulvalene 基于吲哚二噻吩-扩展四噻吩的受体-供体-受体体系

IF 2.5 3区化学

European Journal of Organic Chemistry Pub Date : 2025-04-01 DOI: 10.1002/ejoc.202401413

Christina Schøttler , Célia Noël , Laura Le Bras , Hayley Melville , Olivier Alévêque , Arthur H. G. David , Olivier Segut , Maxime Rémond , Eric Levillain , Philippe Blanchard , Mogens Brøndsted Nielsen

{"title":"Acceptor‐Donor‐Acceptor Systems Based on Indacenodithiophene‐Extended Tetrathiafulvalene","authors":"Christina Schøttler , Célia Noël , Laura Le Bras , Hayley Melville , Olivier Alévêque , Arthur H. G. David , Olivier Segut , Maxime Rémond , Eric Levillain , Philippe Blanchard , Mogens Brøndsted Nielsen","doi":"10.1002/ejoc.202401413","DOIUrl":"10.1002/ejoc.202401413","url":null,"abstract":"<div><div>Here, we present a series of acceptor‐donor‐acceptor (A−D‐A) conjugated molecules incorporating an indacenodithiophene‐extended tetrathiafulvalene (IDT‐TTF) as the central electron‐donating moiety, functionalized with various lateral electron acceptors. A key synthetic step was the Vilsmeier‐Haack formylation of the IDT‐TTF, providing the dialdehyde in quantitative yield. This compound was further used for the incorporation of dicyanovinyl and indanedione acceptors. UV‐vis absorption spectroscopy of the A−D‐A compounds in solution revealed a broad absorption in the visible spectrum which is further red‐shifted when proceeding from solutions to thin films. Their cyclic voltammograms in solution showed a multi‐redox behavior – undergoing both oxidation and reduction events. Notably, the oxidation of these compounds unveiled the formation of intermolecular mixed‐valence and π‐dimer species, especially strong in the case of the indanedione‐containing derivative. Computational calculations helped us to identify the electronic transitions involved in the main absorption bands of these A−D‐A compounds displaying different behaviors depending on the acceptor attached to the IDT‐TTF core. Finally, the potential of these compounds as donors in organic solar cells was investigated and the best performing solar cell exhibited a modest yet promising power conversion efficiency of 0.87 %.</div></div>","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"28 13","pages":"Article e202401413"},"PeriodicalIF":2.5,"publicationDate":"2025-04-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/ejoc.202401413","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143385091","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

Determination of the pKaH of Established Isothiourea Catalysts 既定异硫脲催化剂pKaH的测定

IF 2.5 3区化学

European Journal of Organic Chemistry Pub Date : 2025-04-01 DOI: 10.1002/ejoc.202401412

Lukas S. Vogl , Matthias Bechmann , Mario Waser

引用次数: 0