Ariful Islam, Gaurav K. Rastogi, Amit Kumar Pathak, Subrata Ghosh, Mohit L. Deb, Pranjal K. Baruah
{"title":"Harnessing a novel organophotocatalyst for C‐H functionalization and E‐Z isomerization","authors":"Ariful Islam, Gaurav K. Rastogi, Amit Kumar Pathak, Subrata Ghosh, Mohit L. Deb, Pranjal K. Baruah","doi":"10.1002/ejoc.202500468","DOIUrl":"https://doi.org/10.1002/ejoc.202500468","url":null,"abstract":"Organic chemistry continues to evolve by discovering and applying novel catalytic systems that enable efficient and selective transformations. Herein, we report on developing and utilizing a newly synthesized organophotocatalyst for C‐H functionalization and isomerization reactions. A pyridazine derivative is successfully used here as a photocatalyst to synthesize 1,3‐oxazines via C‐H functionalizations of Betti bases (a‐aminoalkyl naphthols) and for the E‐Z isomerization of 2‐(alkylthio)‐substituted‐1,4‐enedione derivatives. A tentative mechanism is also proposed for the catalytic behavior of the novel photocatalyst.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"11 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-06-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144260157","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}
{"title":"Pd-Catalyzed C-H Activation and Oxidative Annulation to Access N-methoxy-7H-Chromenoquinolinones and N-methoxyphenyl quinolinones","authors":"Harishankar Behera, Suhasini Mohapatra, Sabita Nayak, Seetaram Mohapatra, Tapaswini Pati, Kamalika Prusty","doi":"10.1002/ejoc.202500107","DOIUrl":"https://doi.org/10.1002/ejoc.202500107","url":null,"abstract":"The palladium-catalyzed oxidative annulation of N-methoxy-2H-chromene-3-carboxamides and N-methoxycinnamamides with benzynes via C-H functionalization to synthesize N-methoxy-7H-Chromenoquinolinones and N-methoxyphenylquinolinones have been developed successfully. The reaction demonstrates broad compatibility with different substrates, high tolerance for various functional groups, and excellent regioselectivity. By carefully selecting substituted arynes, exceptional regioselectivity can be achieved. The structure of a key product was confirmed through X-ray crystallography, further validating the efficiency and success of the reaction.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"49 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-06-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144260839","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}
Pascal Paquin, Nicolas DeGrâce, Guillaume Bélanger-Chabot, Jean-François Paquin
{"title":"Gold‐catalyzed synthesis of substituted 4‐pentafluorosulfanyl‐1,3‐oxazoles","authors":"Pascal Paquin, Nicolas DeGrâce, Guillaume Bélanger-Chabot, Jean-François Paquin","doi":"10.1002/ejoc.202500348","DOIUrl":"https://doi.org/10.1002/ejoc.202500348","url":null,"abstract":"We report the first synthesis of pentafluorosulfanylated oxazoles through a gold(I) catalyzed cyclization of SF5‐alkynes and nitriles. We describe 17 examples of 4‐SF5‐oxazoles with NMR yield ranging from 3% to 75%. While the isolation of the pure pentafluorosulfanylated oxazoles proved challenging, the fluorinated heterocycles could nonetheless be obtained in yields between 14 and 52%, opening the door for their use as a novel fluorine‐containing scaffold.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"63 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-06-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144268586","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}
{"title":"Covalent Organic Framework Films: Preparation, Properties, and Applications","authors":"Qinchen Jiang, Weijie Yang, Qianwei Xu, Qiaoyu Wang, Keqian Wang, Xiang-Chun Li, Wen-Yong Lai","doi":"10.1002/ejoc.202500569","DOIUrl":"https://doi.org/10.1002/ejoc.202500569","url":null,"abstract":"Covalent organic frameworks (COFs), as a class of crystalline porous materials, have attracted substantial interest due to their tunable structures and diverse functionalities. This review examines recent advancements in the preparation of COF films, with a particular focus on the strategies employed to synthesize these materials while achieving high crystallinity and porosity. The challenges encountered during the synthesis and application of COF films are discussed, including the necessity for scalable production methods and the optimization of their properties for practical applications. Current research and innovation efforts in the field of COF films are poised to broaden their potential applications across various domains. Although the synthesis of large-scale single-crystal COF films presents significant challenges, the progress observed in this area offers promising avenues for unlocking the full potential of COF films in electronic and optoelectronic applications.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"17 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-06-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144260840","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}
Fusheng Li, Tao Huang, Xiaoxia He, Zulin Xiao, Juan Liu
{"title":"The Novel Radical‐Based Strategies for the Construction of α‐Allenols","authors":"Fusheng Li, Tao Huang, Xiaoxia He, Zulin Xiao, Juan Liu","doi":"10.1002/ejoc.202500448","DOIUrl":"https://doi.org/10.1002/ejoc.202500448","url":null,"abstract":"α‐Allenols have become common advanced synthons for the synthesis of various of structures and are a frequent motif in natural products and pharmaceuticals. The special reactivity could occur due to the synergistic effect of the allene and hydroxy functional groups. Thus, many remarkable and elegant protocols have been explored through ionic pathways for the construction of α‐allenols. Recently, the rapid growth of radical chemistry has provided an alternative strategy to obtain α‐allenols through single‐electron transfer. As compared to the ionic pathway, the radical pathway has clear advantages, such as mild conditions, high efficiency, and excellent selectivity control. In this Review, we summarize the most important contributions for the construction of α‐allenols via radical intermediates by categorizing them into different types of substrates. Additionally, mechanistic studies and synthetic challenges are highlighted.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"173 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-06-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144260158","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}
Ameneh Tatar, Martin Havlík, Tereza Navrátilová, Tereza Uhlíková, Michaela Drozdová, Karolína Hricková, Jan Hajduch, Pavel Anzenbacher, Bohumil Dolensky
{"title":"On the Preparation of Nickel Porphyrins Bearing Two to Four Nitro Groups at β‐Positions","authors":"Ameneh Tatar, Martin Havlík, Tereza Navrátilová, Tereza Uhlíková, Michaela Drozdová, Karolína Hricková, Jan Hajduch, Pavel Anzenbacher, Bohumil Dolensky","doi":"10.1002/ejoc.202500420","DOIUrl":"https://doi.org/10.1002/ejoc.202500420","url":null,"abstract":"The preparation, isolation, and identification of dinitro, trinitro, and tetranitro metalloporphyrins bearing nitro groups on pyrrole rings—desirable intermediates that enable fundamental changes in the chemico‐physical properties of the porphyrin core—were studied. All six possible dinitro‐Ni‐TPP isomers were formed; three were isolated as pure substances using column chromatography, while the remaining three were inseparable. All possible trinitro‐Ni‐TPP isomers were prepared and isolated, except for the 2,7,13 isomer. Attempts to synthesize tetranitro‐Ni‐TPP either through direct nitration of metalloporphyrin or via direct condensation of the nitropyrrole building blocks were unsuccessful. The molecular structures were unambiguously identified using 2D NMR experiments. Some experimental observations, though not all, were consistent with quantum chemical calculations performed on the geometry, energy, Fukui indices, dipole moments of nitroporphyrins, and the energy of nitration intermediates.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"12 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-06-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144268587","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}
Mateusz Klarek, Tim Schäfer, Aleksander Gorski, Natalia Dutkiewicz, Paweł Hikisz, Magdalena Gapińska, Damian Trzybiński, Krzysztof Woźniak, Jens Müller, Konrad M. Kowalski
{"title":"Luminescent click‐pyrenyl nucleosides as novel building blocks for nucleic acids: synthesis, photophysics, confocal microscopy studies and oligonucleotide conjugation","authors":"Mateusz Klarek, Tim Schäfer, Aleksander Gorski, Natalia Dutkiewicz, Paweł Hikisz, Magdalena Gapińska, Damian Trzybiński, Krzysztof Woźniak, Jens Müller, Konrad M. Kowalski","doi":"10.1002/ejoc.202500559","DOIUrl":"https://doi.org/10.1002/ejoc.202500559","url":null,"abstract":"We report the synthesis of dinucleoside analogues with a “pyrenyl‐triazole‐N‐(triazole)2” linker substituting the natural phosphodiester linkage. The compounds were obtained stepwise with the copper‐catalyzed Huisgen (3+2) azide alkyne cycloaddition reaction of azidopyrene tripropargylamine, and the respective nucleoside azide. Due to the presence of the pyrenyl entity, compounds show unimolecular (in diluted solutions) or excimer (at higher concentrations and in the solid state) emission. Luminescence allowed to track their spatial distribution inside living MCF‐7 cells by using confocal microscopy. The compounds showed am affinity to lipid membranes and localize in a form of granules or larger aggregates in the area of the cytosol including, in particular, the perinuclear region. Representative nucleoside was appended to the 5’‐terminus of the deoxyribonucleotide 5’‐d(TTT CTT TCC CTC)‐3’. The resulting conjugate forms stable B‐type DNA duplex with complementary oligonucleotide.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"41 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-06-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144268589","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}
Timo A. Zschau, Kathin Bensberg, Cedric Meysing, Nofisa Lamuadni, Adrián Gómez Suárez, Stefan F Kirsch
{"title":"Upcycling Food Waste: Ursolic Acid as Sustainable Feedstock","authors":"Timo A. Zschau, Kathin Bensberg, Cedric Meysing, Nofisa Lamuadni, Adrián Gómez Suárez, Stefan F Kirsch","doi":"10.1002/ejoc.202500422","DOIUrl":"https://doi.org/10.1002/ejoc.202500422","url":null,"abstract":"Herein, we present a sustainable strategy to access the ursane class of natural products. Our complexity-controlling synthesis (CCS) approach employs ursolic acid – readily obtained from apple pomace, a waste product of apple juice production – as sustainable feedstock to access 24 natural products of the ursane family in short synthetic sequences (1–12 steps) and good yields (up to 98%).","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"257 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-06-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144260782","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}
Jin-Kui Liu, Jiayu Niu, Bo Zhang, Xiuge Hao, Mao-Ping Song, Hui Jiang, Jun-Fang Gong
{"title":"Catalytic Behavior of Cobalt Complexes Bearing Imine‐Pyridine‐Oxazoline Ligands in Isoprene Polymerization","authors":"Jin-Kui Liu, Jiayu Niu, Bo Zhang, Xiuge Hao, Mao-Ping Song, Hui Jiang, Jun-Fang Gong","doi":"10.1002/ejoc.202500471","DOIUrl":"https://doi.org/10.1002/ejoc.202500471","url":null,"abstract":"A series of cobalt complexes bearing imine‐pyridine‐oxazoline ligands were successfully synthesized and characterized. Upon activation with diethylaluminum chloride (AlEt2Cl), these cobalt complexes exhibited high catalytic activity in isoprene polymerization and provided cis‐1,4‐co‐3,4 polyisoprene (cis‐1,4/3,4 ≈ 2:1). Among them, a complex featuring a diphenylmethyl substituent, demonstrated the highest thermal stability, maintaining a catalytic activity of up to 1.06×105 g·mol‐1·h‐1 at 70 °C. Single‐crystal X‐ray diffraction analysis showed that this complex adopted a trigonal bipyramidal configuration via N,N,N‐tridentate coordination to cobalt center. Both the ligand architecture and the polymerization temperature were found to play critical roles in determining the catalytic performance and the structural properties of the resulting polymers. Furthermore, the influence of various polymerization parameters on catalytic activity and selectivity was systematically investigated.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"57 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-06-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144260159","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}
Safomuddin Abduahadi, Emmanuel Mintah Bonku, Fuqiang Zhu, Feipu Yang, Samuel Desta Guma, Zayniddin Nuriddinov, Hongjian Qin, Jingshan Shen
{"title":"An Efficient Asymmetric Synthesis of Finerenone via Evans' Chiral Auxiliary","authors":"Safomuddin Abduahadi, Emmanuel Mintah Bonku, Fuqiang Zhu, Feipu Yang, Samuel Desta Guma, Zayniddin Nuriddinov, Hongjian Qin, Jingshan Shen","doi":"10.1002/ejoc.202500538","DOIUrl":"https://doi.org/10.1002/ejoc.202500538","url":null,"abstract":"This article reports a new application of Evans' chiral auxiliary for an efficient asymmetric synthesis of finerenone. This new application successfully achieves the key step of stereoselective construction of the naphthyridine core of finerenone, with a high diastereomeric ratio (dr 86:14) and an 80% yield of the desired product via Evans’ chiral (R)-4-benzyl-2-oxazolidinone. The downstream transamidation of ethyl ester, with ammonia, leads to the formation of finerenone.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"100 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-06-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144260784","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}