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Fluorinated Aminophosphonates and Aminophosphonic Acids: A Journey Through Recent Advances 氟化氨基膦酸盐和氨基膦酸：最新进展之旅
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-06-23 DOI: 10.1002/ejoc.202500510
Tomasz Cytlak, Monika Bilska-Markowska, Marcin Kaźmierczak
{"title":"Fluorinated Aminophosphonates and Aminophosphonic Acids: A Journey Through Recent Advances","authors":"Tomasz Cytlak, Monika Bilska-Markowska, Marcin Kaźmierczak","doi":"10.1002/ejoc.202500510","DOIUrl":"https://doi.org/10.1002/ejoc.202500510","url":null,"abstract":"This review aims to summarise the most recent developments in the chemistry of fluorinated aminophosphonates and aminophosphonic acids, with a particular focus on literature published since the turn of 2016/2017. Fluorinated derivatives of aminophosphonates and aminophosphonic acids represent a rapidly growing area of interest due to their unique chemical properties and potential applications in various fields, including medicinal and agricultural chemistry. In this work, special emphasis is placed on highlighting the most significant reports concerning selective and efficient synthetic methodologies for these compounds. Particular attention is given to strategies that offer high yields, regio‐ or stereoselectivity, and operational simplicity, including direct fluorination, addition reactions, as well as catalytic and radical processes. Additionally, the review discusses the potential practical applications of these fluorinated derivatives, such as their roles as enzyme inhibitors, bioisosteres of amino acids, and potential pharmaceuticals.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"51 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-06-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144370590","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
Decarboxylative Michael Additions of Substituted Malonic Acid Half‐Oxyesters to Methylidene Malonates 取代丙二酸半氧酯对丙二酸甲酯的脱羧作用
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-06-23 DOI: 10.1002/ejoc.202500457
Marine Pinaud, Tania Xavier, Léa Lin, Erwan Le Gall, Marc Presset
{"title":"Decarboxylative Michael Additions of Substituted Malonic Acid Half‐Oxyesters to Methylidene Malonates","authors":"Marine Pinaud, Tania Xavier, Léa Lin, Erwan Le Gall, Marc Presset","doi":"10.1002/ejoc.202500457","DOIUrl":"https://doi.org/10.1002/ejoc.202500457","url":null,"abstract":"Decarboxylative Michael additions between substituted malonic acids half oxyesters (SMAHOs) and methylidene malonates have been achieved using either a catalytic amount of a weak base such as N‐methyl‐morpholine (NMM) or di‐iso‐propylamine (DIPEA) in a refluxing solvent. This transformation occurs under practical conditions (bulk solvent and open to air) and can be performed with various SMAHOs and methylidene malonates, in yields ranging from 22 to 89%. NMR studies support the occurrence of a Michael addition pre‐decarboxylation mechanism.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"49 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-06-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144370626","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 of Amphiphilic Naphthalenediimides and Investigation of Their Bioimaging Potential in Large Unilamellar Vesicles 两亲性萘二亚胺的合成及其在大单层囊泡中的生物成像潜力研究
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-06-23 DOI: 10.1002/ejoc.202500363
Francesca Cardano, Federica Micheletto, Giada Fregnan, Giacomo Renno, Paolo Ettore Porporato, Andrea Fin
{"title":"Synthesis of Amphiphilic Naphthalenediimides and Investigation of Their Bioimaging Potential in Large Unilamellar Vesicles","authors":"Francesca Cardano, Federica Micheletto, Giada Fregnan, Giacomo Renno, Paolo Ettore Porporato, Andrea Fin","doi":"10.1002/ejoc.202500363","DOIUrl":"https://doi.org/10.1002/ejoc.202500363","url":null,"abstract":"New fluorescent probes for bioimaging outlook are constantly required to in depth elucidate relevant biochemical processes and macrodomains. Among them the targeted imaging of cellular membranes is of high importance due to their complex biochemical function. In this work, a small library of amphiphilic core substituted 1,4,5,8-naphthalenediimides (cNDIs) has been synthesized and investigated. This approach aims to evaluate how fluorophores with the same molecular structure and hydrophilic/hydrophobic balance but bearing different small structural moieties, needed to tune their optical features, can stain the lipid bilayer membrane in large unilamellar vesicles (LUVs) as cell membrane models. The photophysical properties and the partition kinetic into different LUVs have been analysed with respect to the probe structure and the specific photophysical traits related to cNDIs core substitution spanning the whole visible spectrum. The obtained results and preliminary cell imaging analyses represent versatile key data to support the design of new amphiphilic fluorescent sensors for bioimaging.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"38 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-06-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144341379","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
Exploring the Impact of Topological Variations on the Stability of the Ground Singlet and Lowest-Lying Triplet States of Catacondensed Hexabenzenoids 探索拓扑变化对六苯类化合物底单重态和最低三重态稳定性的影响
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-06-20 DOI: 10.1002/ejoc.202500376
Iqra Sarfraz, Anna Roglans, Albert Artigas, Miquel Solà
{"title":"Exploring the Impact of Topological Variations on the Stability of the Ground Singlet and Lowest-Lying Triplet States of Catacondensed Hexabenzenoids","authors":"Iqra Sarfraz, Anna Roglans, Albert Artigas, Miquel Solà","doi":"10.1002/ejoc.202500376","DOIUrl":"https://doi.org/10.1002/ejoc.202500376","url":null,"abstract":"Polycyclic aromatic hydrocarbons (PAH) like tetracenes, pentacenes, hexacenes, and some higher acenes play a central role in organic electronics due to their unique electronic properties. The impact of topological variations on the relative stability of PAH isomers in different electronic states is poorly understood, with limited insights into how Clar p-sextets and topological features like bay, cove, fjord, and K-regions influence stability in their ground singlet (S0) and lowest-lying triplet (T1) states. In this work, we perform density functional theory calculations of the S0 and T1 states of the 37 catacondensed hexabenzenoids. We use a multivariate linear regression model with relative energy as the dependent variable and a series of topological parameters as the independent variables to quantify the effect of topology in the relative stability of the catacondensed hexabenzenoids. Our analysis shows that, in S0, stability is enhanced by an increase in the number of Clar p-sextets and K-regions and decreased by the presence of coves and fjords. In T1, the main stabilizing factors are the number of Clar p-sextets and the number of rings involved in the antiaromatic region, whereas topological regions like K-edges, bays, coves, or fjords are destabilizing.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"13 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-06-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144329360","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
Eco-Friendly Borylation of Allylic Acetates via Nickel-Catalyzed Dual-Role Base Activation 镍催化双作用碱活化丙烯酸酯的生态友好型硼化反应
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-06-20 DOI: 10.1002/ejoc.202500319
Ziyi Quan, Yaxu Liu, Aihua Zhen, Fengcui Ma, Xiang Gao, Jifu Sun, Bo Wang
{"title":"Eco-Friendly Borylation of Allylic Acetates via Nickel-Catalyzed Dual-Role Base Activation","authors":"Ziyi Quan, Yaxu Liu, Aihua Zhen, Fengcui Ma, Xiang Gao, Jifu Sun, Bo Wang","doi":"10.1002/ejoc.202500319","DOIUrl":"https://doi.org/10.1002/ejoc.202500319","url":null,"abstract":"Allylic boronates are valuable synthons in organic chemistry, making the development of efficient and sustainable preparation methods highly desirable. We report a nickel-catalyzed borylation of unactivated allylic acetates using a recyclable N-donor ligand system in ethyl acetate. The method employs an innovative dual-role base that simultaneously activates diboron reagents and reduces air-stable NiBr2, eliminating need for external reductants. The approach shows excellent compatibility across a diverse array of substrates, delivering the desired products with isolated yields up to 97%. Its operational simplicity is evidenced by glovebox-free conditions and successful multi-gram scale implementation (13 mmol scale, yields up to 95%), underscoring the method's practicality as a eco-friendly alternative to conventional allylic borylation.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"19 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-06-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144329359","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
NHC‐based Photoswitches in Catalysis: Recent Developments and Challenges 催化中基于NHC的光开关：最近的发展和挑战
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-06-20 DOI: 10.1002/ejoc.202500362
Gilles Alcaraz, Lucie Jarrige
{"title":"NHC‐based Photoswitches in Catalysis: Recent Developments and Challenges","authors":"Gilles Alcaraz, Lucie Jarrige","doi":"10.1002/ejoc.202500362","DOIUrl":"https://doi.org/10.1002/ejoc.202500362","url":null,"abstract":"Using light as an external stimulus, photoswitchable catalysis offers the attractive opportunities to modulate the activity and selectivity of catalytic systems on demand and remotely, with high spatial and temporal precision. Consequently, the development of photoswitchable catalyst has attracted considerable attention from the chemist community in recent decades, leading to various photoresponsive species with diverse properties. Among these, only a few examples incorporate N‐heterocyclic carbenes (NHCs), despite their unique electronic and steric properties and their ubiquity in organic and organometallic catalysis. This review highlights recent advances in this emerging research area from the first reported species in 2009 to the present day, with particular emphasis on the synthesis of photoswitchable NHCs and their corresponding transition metal complexes for application in catalysis. Future perspectives in the field are also discussed.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"237 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-06-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144334891","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 Multicomponent aza‐Prins Strategy for the Diastereoselective Synthesis of Piperidine Fused Dihydroquinazolinones 多组分aza - Prins策略非对映选择性合成哌啶融合二氢喹啉酮
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-06-19 DOI: 10.1002/ejoc.202500368
Lovisa Dybeck, Morgane Baudoin, Luke Robert Odell
{"title":"A Multicomponent aza‐Prins Strategy for the Diastereoselective Synthesis of Piperidine Fused Dihydroquinazolinones","authors":"Lovisa Dybeck, Morgane Baudoin, Luke Robert Odell","doi":"10.1002/ejoc.202500368","DOIUrl":"https://doi.org/10.1002/ejoc.202500368","url":null,"abstract":"Dihydroquinazolinones and piperidines are widely acknowledged as privileged structures and are of significant interest for the development of new drug candidates. Herein we present a novel aza‐Prins strategy for the synthesis of piperidine fused dihydroquinazolinones through a domino multicomponent reaction. Homoallylic ammonium halide salts were found to react with bifunctional aldehydes under acidic conditions to give halide substituted fused piperidines in a diastereoselective fashion. The reaction could be extended to the incorporation of alcohol nucleophiles via fine tuning of the reaction conditions. Finally, the utility of the substituted compounds was shown by performing a variety of functionalization reactions on the scaffold.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"36 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-06-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144319461","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
Aggregation‐Induced Asymmetric Synthesis of 2,3‐Dihydrobenzofurans by [4 + 1] Annulation with Substituted Salicyl N‐Phosphonyl Imines [4 + 1]环化取代水杨基N -膦酰亚胺聚合诱导不对称合成2,3 -二氢苯并呋喃
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-06-18 DOI: 10.1002/ejoc.202500426
Guigen Li, Qingkai Yuan, Jasmine Yan, Hao Liu, Destin Mununga Maleka, Eric Augusto Eichelmann, Olivia Villanueva, Anthony F. Cozzolino
{"title":"Aggregation‐Induced Asymmetric Synthesis of 2,3‐Dihydrobenzofurans by [4 + 1] Annulation with Substituted Salicyl N‐Phosphonyl Imines","authors":"Guigen Li, Qingkai Yuan, Jasmine Yan, Hao Liu, Destin Mununga Maleka, Eric Augusto Eichelmann, Olivia Villanueva, Anthony F. Cozzolino","doi":"10.1002/ejoc.202500426","DOIUrl":"https://doi.org/10.1002/ejoc.202500426","url":null,"abstract":"The aggregation‐induced asymmetric synthesis of trans‐2,3‐dihydrobenzofuran compounds was achieved via the reaction of salicyl N‐phosphonyl imines with sulfur ylide. This transformation proceeds through a [4 + 1] annulation pathway, affording products in good to excellent yields with tunable diastereoselectivities. By employing various THF/EtOH cosolvent systems in conjunction with group‐assisted purification (GAP) chemistry, the conventional aggregation cosolvent systems were shown to play a crucial role in enhancing diastereoselectivity and modulating aggregate formation. This was supported by studies involving aggregation‐induced emission (AIE), aggregation‐induced polarization (AIP), and dynamic light scattering (DLS). The developed protocol provides a practical and versatile synthetic approach to 2,3‐dihydrobenzofuran scaffolds, highlighting the utility of aggregation‐induced asymmetric synthesis (AIAS) as a powerful strategy for achieving stereocontrol.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"30 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-06-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144311414","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
Electrochemical gem-Bisarylation of Hydrazone: Access to Bis(indolyl)methane 腙的电化学宝石-双芳基化：获得双（吲哚基）甲烷
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-06-17 DOI: 10.1002/ejoc.202500515
Hui Meng, Jing Feng, Mingqi Yang, Mingming Yu, Zefeng Xu, Chuanying Li
{"title":"Electrochemical gem-Bisarylation of Hydrazone: Access to Bis(indolyl)methane","authors":"Hui Meng, Jing Feng, Mingqi Yang, Mingming Yu, Zefeng Xu, Chuanying Li","doi":"10.1002/ejoc.202500515","DOIUrl":"https://doi.org/10.1002/ejoc.202500515","url":null,"abstract":"An electrochemical organic method for the direct synthesis of bis(indolyl)methane derivatives is presented, with the reaction of hydrazones and indoles. This developed approach is effective for aliphatic, aromatic, and heteroaromatic aldehydes, which react with a range of electron-rich and electron-poor indoles to produce the desired BIMs in good to excellent yields. Additionally, potential antiobesity drug was also successfully synthesized with various indole derivatives under the influence of an electric current, and the transformation of BIMs demonstrated the application potential of this protocol.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"12 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-06-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144305428","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
Photoredox Decarboxylative 3-Fluoroallylation of α-Amino Acids α-氨基酸的光氧化还原脱羧3-氟烯丙基化
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-06-17 DOI: 10.1002/ejoc.202500519
Taylor Semeniuk, Jacob Challenger, Ty Dudas, Dennis Toporkov, Miriam D. van Hoeve, Jean-Denys Hamel
{"title":"Photoredox Decarboxylative 3-Fluoroallylation of α-Amino Acids","authors":"Taylor Semeniuk, Jacob Challenger, Ty Dudas, Dennis Toporkov, Miriam D. van Hoeve, Jean-Denys Hamel","doi":"10.1002/ejoc.202500519","DOIUrl":"https://doi.org/10.1002/ejoc.202500519","url":null,"abstract":"The photocatalytic decarboxylation of α-amino acids is an effective route to α-aminoalkyl radicals which is also amenable to the derivatization of peptides through selective C–C bond formation at the C-terminus. We report that, in the presence of an iridium photocatalyst, allylic difluorides are suitable radical traps to capture α-aminoalkyl radicals produced from α-amino acids, ultimately amounting to a defluorinative 3-fluoroallylation reaction. The catalytic system was applied to the derivatization of a wide breadth of N-protected amino acids and dipeptides in high yields, and the transformation displays great functional group tolerance. α-Amino acids of all substitution levels at the α-carbon led to the desired products in high yields. Post-functionalization of the monofluoroalkene-containing products revealed the potential to attain fluorine-containing organic compounds of greater complexity.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"11 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-06-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144305450","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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