European Journal of Organic Chemistry最新文献_第4页

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}

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All-Visible-Light Diarylethene Photoswitches and Control over Dynamic Conjugate Addition Reactions 全可见光二乙烯光开关及动态共轭加成反应的控制

IF 2.8 3区化学

European Journal of Organic Chemistry Pub Date : 2025-09-28 DOI: 10.1002/ejoc.202500660

Guozhen Wu, Hanwei Lu, Hebo Ye, Jiafan Xin, Lei You

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Copper-Catalyzed Diastereo- and Enantioselective 1,3-Dipolar Cycloaddition of Imino Lactones with Ylidene-Pyrazolones 铜催化酰基吡唑酮与亚胺内酯的非映对和对映选择性1,3-偶极环加成反应

IF 2.8 3区化学

European Journal of Organic Chemistry Pub Date : 2025-09-28 DOI: 10.1002/ejoc.202500409

Kenji Muroi, Shohei Furuya, Shin-ichi Fukuzawa

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Activation in Organic and Macromolecular Including Peptide Synthesis by Fluorinated Carboxylic Acids and Derivatives 氟化羧酸及其衍生物在有机和大分子包括肽合成中的活化作用

IF 2.8 3区化学

European Journal of Organic Chemistry Pub Date : 2025-09-28 DOI: 10.1002/ejoc.202500776

Virgil Percec, Jasper Adamson, Devendra S. Maurya

{"title":"Activation in Organic and Macromolecular Including Peptide Synthesis by Fluorinated Carboxylic Acids and Derivatives","authors":"Virgil Percec, Jasper Adamson, Devendra S. Maurya","doi":"10.1002/ejoc.202500776","DOIUrl":"https://doi.org/10.1002/ejoc.202500776","url":null,"abstract":"This concept article discusses recent developments in activated esters, including fluorinated activated esters and other activated carboxylic acid derivatives. Activated carboxylic acid derivatives, including esters, are of interest since 1901 when Emil Fischer prepared the first peptide, and soon after, for the synthesis of Nylons, Kevlar, and other condensation polymers. Since the synthesis of sequence-defined peptides and methodologies for their construction relied mostly on the development of activated ester derivatives, the preparation of the peptide and amide bond is used as a strategy for the organization and the development of this concept article. Therefore, the acyl chlorides, anhydrides, numerous nonfluorinated activated esters, and fluorinated activated esters, including pentachlorophenyl, pentafluorophenyl, hexafluoroisopropyl, and other fluorinated esters, will be discussed in aminolysis and transesterification reactions. The synthesis of peptide and amide bond, the modification of polymers, the bioorthogonal chemistry, and the living chain-growth condensation polymerization are also briefly discussed. This concept article ends with a brief mention of the resurgence of acyl fluoride in organic and macromolecular chemistry.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"118 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-09-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145183093","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}

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Visible Light-Promoted Aerobic Oxidation of Boronic Acids and Esters Utilizing a Benzothioxanthene Imide as the Photocatalyst 以苯并噻吩亚胺为光催化剂，可见光促进硼酸和硼酸酯的好氧氧化

IF 2.8 3区化学

European Journal of Organic Chemistry Pub Date : 2025-09-27 DOI: 10.1002/ejoc.202500782

Stamatis K. Serviou, Petros L. Gkizis, Darío Puchán Sánchez, Soussana Azar, Arthur H. G. David, Clement Cabanetos, Christoforos G. Kokotos

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The Reactivity of α‐Fluorinated Mono‐ and Diketones Uncovers their Potential as Electrophilic Warheads for Reversible Covalent Drugs α-氟化单酮和二酮的反应性揭示了它们作为可逆共价药物亲电战斗部的潜力

IF 2.7 3区化学

European Journal of Organic Chemistry Pub Date : 2025-09-26 DOI: 10.1002/ejoc.202500380

Yossi Zafrani , Ido Michael Herzog , Eliav Blum , Shlomi Elias , Sigal Saphier , Ishay Columbus

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Two Metals, One Goal: Unlocking Reactivity with Heterobimetallic Systems for Organic Transformations 两种金属，一个目标：解锁有机转化的异双金属体系的反应性

IF 2.7 3区化学

European Journal of Organic Chemistry Pub Date : 2025-09-26 DOI: 10.1002/ejoc.202500463

Madhuri P. Rao , Madhu Ganesh

{"title":"Two Metals, One Goal: Unlocking Reactivity with Heterobimetallic Systems for Organic Transformations","authors":"Madhuri P. Rao , Madhu Ganesh","doi":"10.1002/ejoc.202500463","DOIUrl":"10.1002/ejoc.202500463","url":null,"abstract":"<div><div>The design of heterobimetallic catalysis is redefining the frontiers in organic synthesis by harnessing the combined power of two distinct metals. It maneuvers a powerful platform in advancing organic transformations through leveraging cooperative synergetic effect of bimetals. In this review, this study unveils heterobimetallic systems that unlock challenging bond activations and novel reaction pathways inaccessible to traditional monometallic systems. It highlights key examples across diverse reaction classes of organic transformation paving way for alkylation, alkenylation, arylation, annulation, cross‐coupling, and oxidative and decarboxylative coupling reactions for the synthesis of pharmaceutically and industrially relevant molecules. The review consolidates on the current updates on the reactions, mechanism, catalytic cycle, and their synthetic transformations. Heterobimetallic catalysts deliver amplified reactivity, expanded substrate diversity, and sharpened selectivity profiles. The bimetallic catalytic system orchestrates multielectron redox‐processes, dual‐site activation, and high turnover numbers. The review concludes with a brief outlook on the future scope, offering a blueprint for next‐generation catalytic platforms that push the boundaries of molecular construction.</div></div>","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"28 35","pages":"Article e202500463"},"PeriodicalIF":2.7,"publicationDate":"2025-09-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145181534","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}

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Synthesis and Physicochemical Characterization of 6‐Trifluoromethyl Spiro[3.3]Heptane Building Blocks 6‐三氟甲基螺[3.3]庚烷结构块的合成与理化表征

IF 2.7 3区化学

European Journal of Organic Chemistry Pub Date : 2025-09-26 DOI: 10.1002/ejoc.202500587

Oleksandr S. Olifir , Pavlo R. Lenda , Anton V. Chernykh , Daria S. Klymenko , Oleksandr S. Liashuk , Svetlana V. Shishkina , Ivan S. Kondratov , Oleksandr O. Grygorenko

{"title":"Synthesis and Physicochemical Characterization of 6‐Trifluoromethyl Spiro[3.3]Heptane Building Blocks","authors":"Oleksandr S. Olifir , Pavlo R. Lenda , Anton V. Chernykh , Daria S. Klymenko , Oleksandr S. Liashuk , Svetlana V. Shishkina , Ivan S. Kondratov , Oleksandr O. Grygorenko","doi":"10.1002/ejoc.202500587","DOIUrl":"10.1002/ejoc.202500587","url":null,"abstract":"<div><div>A practical synthesis of 6‐(trifluoromethyl)spiro[3.3]heptane‐derived building blocks is developed. Starting from a commercially available cyclobutanone derivative, a key building block—1,1‐bis(bromomethyl)‐3‐(trifluoromethyl)cyclobutane—is prepared on a 0.5 kg scale in a single run. Further construction of the spiro[3.3]heptane core is achieved via double alkylation of TosMIC or malonate diester on up to 120 g scale. Simple functional group transformation provides access to a wide range of mono‐ and bifunctional spiro[3.3]heptane‐derived building blocks, including alcohols, amines, boronate esters, carboxylic acids, and amino acids on a gram to multigram scale. Physicochemical properties (i.e., acidity p<em>K</em><sub>a</sub> and lipophilicity Log<em>P</em>) are experimentally determined and compared to those for non‐, mono‐, and <em>gem</em>‐difluorinated counterparts, as well as cyclohexane and cycloheptane derivatives. The spatial structure of the obtained compounds is evaluated by X‐ray diffraction studies and characterized by exit vector plot analysis.</div></div>","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"28 35","pages":"Article e202500587"},"PeriodicalIF":2.7,"publicationDate":"2025-09-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144898831","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}

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Synthesis and Photophysical Analysis of Amphiphilic Azobenzene Surfactants for Photomechanical Actuation 两亲性偶氮苯表面活性剂的合成及光物理分析

IF 2.8 3区化学

European Journal of Organic Chemistry Pub Date : 2025-09-26 DOI: 10.1002/ejoc.202500250

Awatef Ayadi, Jongseong Park, Orein Francis Jafter, Dominik Lungerich

{"title":"Synthesis and Photophysical Analysis of Amphiphilic Azobenzene Surfactants for Photomechanical Actuation","authors":"Awatef Ayadi, Jongseong Park, Orein Francis Jafter, Dominik Lungerich","doi":"10.1002/ejoc.202500250","DOIUrl":"https://doi.org/10.1002/ejoc.202500250","url":null,"abstract":"Photoswitchable amphiphiles are promising candidates for investigating light-responsive mechanical behavior in soft and biological systems, with potential applications in dynamic materials and adaptive interfaces. Azobenzene is the most studied photoactuator, but research typically focuses on its standard backbone, limiting control over its photophysical and kinetic properties. Modifying its conjugated core offers new opportunities for tuning its behavior. Here, the synthesis and characterization of water-soluble azobenzene derivatives featuring a hexaethylene glycol (OCH<sub>2</sub>CH<sub>2</sub>)<sub>6</sub> unit terminated with a sodium sulfate (O<span></span>SO<sub>3</sub>Na) group, alongside subtle electronic modifications to the conjugated backbone, are reported. Their steady-state photophysical properties and reversible photoisomerization kinetics in aqueous environments under real-time observation are demonstrated. Despite similar activation parameters for the thermal <i>cis</i>–<i>trans</i> isomerization in some derivatives, their half-lives vary significantly, underscoring the overlooked role of the transmission coefficient in isomerization kinetics. Finally, these photo-responsive amphiphiles are showcased as dynamic surfactants in oil-in-water and water-in-oil emulsions, visualizing their behavior through operando microscopy. These findings underscore their potential for tunable emulsions and adaptive soft matter applications.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"29 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-09-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145141057","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

Environmental Control of Regio-/Stereoselectivity Across Mechanistically Similar Transformations 机制相似转化中区域/立体选择性的环境控制

IF 2.8 3区化学

European Journal of Organic Chemistry Pub Date : 2025-09-26 DOI: 10.1002/ejoc.202500299

Anushka Asurumunige, Doris Itubo, Kerry Gilmore

{"title":"Environmental Control of Regio-/Stereoselectivity Across Mechanistically Similar Transformations","authors":"Anushka Asurumunige, Doris Itubo, Kerry Gilmore","doi":"10.1002/ejoc.202500299","DOIUrl":"https://doi.org/10.1002/ejoc.202500299","url":null,"abstract":"The control of regio- and stereoselectivity in organic transformations remains a foundational challenge in synthetic chemistry. While chemoselectivity can often be influenced by careful selection of reagents or protective groups, controlling regio- and stereoselectivity is far more nuanced, often requiring highly specific reaction conditions. In this work, a unified approach for controlling both regio- and stereoselectivity across mechanistically related transformations is explored, specifically focusing on epoxide openings and carbonyl additions. It is demonstrated that the same environmental factors, here the nature of the Lewis acid (LA), can be leveraged to influence divergent outcomes in these two reaction types by amplifying inherent differences between reaction sites/faces, leading to highly selective transformations. The systematic evaluation of over 30 Lewis acids revealed a dichotomy between “labile” and “strong” activation modes, where strong LAs, such as AlCl<sub>3</sub> and SnCl<sub>4</sub>, drive the highest levels of regio- and diastereoselectivity for both transformations. Further, there exists nuanced differences between the degree of influence of some LA within these mechanistically related transformations. These findings suggest that environmental factors can be broadly applied across different mechanistic classes to achieve selectivity, offering a versatile strategy for reaction optimization.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"42 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-09-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145153589","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