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Front Cover: Filling the Gap within 10-Membered Heteroenediynes: Thiaenediyne – An Experimental and Theoretical Study (Eur. J. Org. Chem. 47/2024)
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2024-12-20 DOI: 10.1002/ejoc.202484701
Natalia A. Danilkina, Ekaterina A. Khmelevskaya, Andrey A. Shtyrov, Mikhail N. Ryazantsev, Alexander F. Khlebnikov, Elena Yu. Tupikina, Andrey M. Rumyantsev, Alexander S. D'yachenko, Irina A. Balova
{"title":"Front Cover: Filling the Gap within 10-Membered Heteroenediynes: Thiaenediyne – An Experimental and Theoretical Study (Eur. J. Org. Chem. 47/2024)","authors":"Natalia A. Danilkina, Ekaterina A. Khmelevskaya, Andrey A. Shtyrov, Mikhail N. Ryazantsev, Alexander F. Khlebnikov, Elena Yu. Tupikina, Andrey M. Rumyantsev, Alexander S. D'yachenko, Irina A. Balova","doi":"10.1002/ejoc.202484701","DOIUrl":"https://doi.org/10.1002/ejoc.202484701","url":null,"abstract":"<b>The Front Cover</b> illustrates a new member of the heteroenediyne group obtained through Nicholas cyclization. Although thiaenediyne is the least reactive in the Bergman cyclization, its appearance allows the application of NBO analysis to the entire family of benzothiophene-conjugated heteroenediynes, thus substantiating the major role of the heteroatom in the enediyne moiety for the reactivity of enediynes in the Bergman cyclization. More details can be found in the Research Article by I. A. Balova and co-workers (DOI: 10.1002/ejoc.202401127).","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"88 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2024-12-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142867585","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
PHOTOCAT24: The Best of the First Edition
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2024-12-18 DOI: 10.1002/ejoc.202401316
Katy Medrano-Uribe, Sara Cuadros, José J. Garrido-González, Giulio Goti, Daniele Mazzarella, Luca Dell'Amico
{"title":"PHOTOCAT24: The Best of the First Edition","authors":"Katy Medrano-Uribe, Sara Cuadros, José J. Garrido-González, Giulio Goti, Daniele Mazzarella, Luca Dell'Amico","doi":"10.1002/ejoc.202401316","DOIUrl":"https://doi.org/10.1002/ejoc.202401316","url":null,"abstract":"With more than 185 attendees, PHOTOCAT24 has been a real success. The photochemical community is vital and vibrant, as the young researchers that have attending the conference. With the help of light, we can perform unique transformations…and we are sure there will be even more to discover and discuss in the future edition.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"31 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2024-12-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142849700","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
Magnetite: a Green, Sustainable and Recyclable Catalyst for Direct Synthesis of Thioesters by C‐H Activation
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2024-12-17 DOI: 10.1002/ejoc.202400827
Yanina Moglie, Joaquín Marchán-García, Mariana Alvarez, Gabriel Radivoy
{"title":"Magnetite: a Green, Sustainable and Recyclable Catalyst for Direct Synthesis of Thioesters by C‐H Activation","authors":"Yanina Moglie, Joaquín Marchán-García, Mariana Alvarez, Gabriel Radivoy","doi":"10.1002/ejoc.202400827","DOIUrl":"https://doi.org/10.1002/ejoc.202400827","url":null,"abstract":"A green and sustainable approach to the direct synthesis of thioesters has been developed using Fe3O4 as a low‐cost, easily prepared, reusable and environmentally safe catalyst. The cross dehydrogenative coupling (CDC) of various thiols and aldehydes in water, or even in the absence of solvent, using tert‐butylhydroperoxide as oxidant, under ligand and base‐free mild conditions, afforded the corresponding thioesters in good to excellent yields. This simple protocol features broad substrate scope, good compatibility with different functional groups, as well as high atom‐efficiency. The scalability, ease of (magnetic) recovery and reuse of the magnetite catalyst are additional eco‐friendly attributes of this methodology. Moreover, the broad synthetic applications of thioesters further highlight the potential utility of the present protocol.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"49 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2024-12-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142832394","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 Biological Activity of 2,6-Disubstituted 7-Deazapurine Ribonucleosides
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2024-12-17 DOI: 10.1002/ejoc.202401187
Ugnė Šinkevičiūtė, Marcela Dvořáková, Michal Tichý, Soňa Gurská, Kateřina Ječmeňová, Lenka Poštová Slavětínská, Petr Džubák, Marián Hajdúch, Michal Hocek
{"title":"Synthesis and Biological Activity of 2,6-Disubstituted 7-Deazapurine Ribonucleosides","authors":"Ugnė Šinkevičiūtė, Marcela Dvořáková, Michal Tichý, Soňa Gurská, Kateřina Ječmeňová, Lenka Poštová Slavětínská, Petr Džubák, Marián Hajdúch, Michal Hocek","doi":"10.1002/ejoc.202401187","DOIUrl":"https://doi.org/10.1002/ejoc.202401187","url":null,"abstract":"Several series of 2,6-disubstituted 7-deazapurine ribonucleosides were synthesized to investigate their biological activities. The key-intermediate chloronucleosides were prepared by an anion-base glycosylation with 2-amino-6-chloro-7-deazapurine. The target compounds were obtained by diazotation, either Suzuki and Sonogashira reactions in the case of 2-arylethynyl-6-hetaryl nucleosides or two consecutive Suzuki reactions in the case of 2,6-diaryl nucleosides. The sequence of diazotation and the first Suzuki reaction is flexible and can be changed depending on the target compounds. Some of the final nucleosides showed moderate cytotoxic activity against several cancer cell lines and low antagonistic activity against a panel of adenosine receptors.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"46 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2024-12-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142832797","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
Cerium-Catalyzed Ritter-type C-H Amination of Alkylarenes
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2024-12-17 DOI: 10.1002/ejoc.202400935
Renpeng Guan, Tianlin Wang, Elliot L. Bennett, Zhiliang Huang, Jianliang Xiao
{"title":"Cerium-Catalyzed Ritter-type C-H Amination of Alkylarenes","authors":"Renpeng Guan, Tianlin Wang, Elliot L. Bennett, Zhiliang Huang, Jianliang Xiao","doi":"10.1002/ejoc.202400935","DOIUrl":"https://doi.org/10.1002/ejoc.202400935","url":null,"abstract":"Reported here is a photocatalytic strategy for Ritter-type C-H amination of alkylarenes with nitriles. Under the irradiation of blue light and the catalysis of a simple Ce(III) salt, alkylarenes were brominated by CBr3COOH and thereby channeled to the normal Ritter pathway to afford amide products. A wide range of alkylarenes and nitriles were tolerated, with a few equivalents of a nitrile being feasible.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"60 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2024-12-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142832795","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
Front Cover: Strategy for C−H Functionalization of Cubanes: From Stoichiometric Reaction to Catalytic Methodology (Eur. J. Org. Chem. 46/2024)
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2024-12-17 DOI: 10.1002/ejoc.202484601
Masaki Hosaka, Shota Nagasawa, Yoshiharu Iwabuchi
{"title":"Front Cover: Strategy for C−H Functionalization of Cubanes: From Stoichiometric Reaction to Catalytic Methodology (Eur. J. Org. Chem. 46/2024)","authors":"Masaki Hosaka, Shota Nagasawa, Yoshiharu Iwabuchi","doi":"10.1002/ejoc.202484601","DOIUrl":"https://doi.org/10.1002/ejoc.202484601","url":null,"abstract":"<b>The Front Cover</b> illustrates two main methodologies of the C−H functionalization of cubanes: directed <i>ortho-</i>metalation (left) and radical functionalization (right). The design is inspired by “Chinchirorin”, a traditional Japanese dice game. In the picture, the dice (the cubanes) are rolled into a pot (a reaction flask). This illustration shows that hand throwing (a metaphor for a catalytic methodology) the cubane into a reaction pot enables precise C−H functionalization of cubane. More information can be found in the Concept by M. Hosaka, S. Nagasawa and Y. Iwabuchi (DOI: 10.1002/ejoc.202401055).","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"115 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2024-12-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142841827","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
Divergent Synthesis of 4‐Aminotriazoles Through Click Cycloaddition and Generation of Iodonium(III) Triazoles
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2024-12-17 DOI: 10.1002/ejoc.202401273
Takumi Hayashi, Elghareeb E. Elboray, Hina Sudo, Naoko Takenaga, Hiroyuki Satake, Toshifumi Dohi
{"title":"Divergent Synthesis of 4‐Aminotriazoles Through Click Cycloaddition and Generation of Iodonium(III) Triazoles","authors":"Takumi Hayashi, Elghareeb E. Elboray, Hina Sudo, Naoko Takenaga, Hiroyuki Satake, Toshifumi Dohi","doi":"10.1002/ejoc.202401273","DOIUrl":"https://doi.org/10.1002/ejoc.202401273","url":null,"abstract":"The divergent synthesis of 4‐amino‐1,2,3‐triazoles was accomplished through the Cu‐catalyzed cycloaddition of organic azides with alkynyliodonium(III) salts, followed by Cu‐catalyzed triazole‐amine coupling involving treatment with amines and amides. The in situ formation of 1,2,3‐triazole iodonium salts is crucial to this approach, and the utilization of a Cu‐catalyst facilitates cycloaddition and C‐N bond formation. The synthesis of 1,2,3‐triazolyliodonium(III) salts proposed in this study offers advantages, including mild reaction conditions, a broad substrate scope, and operational simplicity, while also providing efficient access to a complex and diverse range of 4‐amino‐1,2,3‐triazole derivatives.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"25 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2024-12-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142832399","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
Front Cover: Merging New and Old Concepts: Tandem Oxidative Radical-Polar Crossover Ritter Amidation via Multicomponent Photo- and Electrochemical Processes (Eur. J. Org. Chem. 45/2024)
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2024-12-16 DOI: 10.1002/ejoc.202484501
Mattia Lepori, Indrasish Dey, Cassie Pratley, Joshua P. Barham
{"title":"Front Cover: Merging New and Old Concepts: Tandem Oxidative Radical-Polar Crossover Ritter Amidation via Multicomponent Photo- and Electrochemical Processes (Eur. J. Org. Chem. 45/2024)","authors":"Mattia Lepori, Indrasish Dey, Cassie Pratley, Joshua P. Barham","doi":"10.1002/ejoc.202484501","DOIUrl":"https://doi.org/10.1002/ejoc.202484501","url":null,"abstract":"<b>The Front Cover</b> showcases the modernization of the Ritter reaction by photo- and electrochemical methods. Historically, carbocation intermediates in Ritter reactions are achieved under strongly acidic conditions that are functional group intolerant. The Review by C. Pratley, J. P. Barham and co-workers (DOI: 10.1002/ejoc.202400840) describes modern radical methods to access carbocation intermediates that allow the expansion of Ritter chemistry to more complex molecules. Radical intermediates, generated photochemically or electrochemically, undergo oxidative radical polar crossover to carbocations that partake in Ritter chemistry to give amidated products. Oxidative radical polar crossover is the “knight's shining armour” (“Ritter” is German for “knight”). Image created by Sarah S. Coutts.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"22 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2024-12-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142825200","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
Solvent-Induced Amplification of Chiral Superstructures of Carbazole Porphyrins in Dynamic Supramolecular Aggregates
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2024-12-13 DOI: 10.1002/ejoc.202401181
Pooja V Shreechippa, Dinesh N Nadimetla, Avinash L. Puyad, Ambadas B. Rode, Sheshanath V. Bhosale
{"title":"Solvent-Induced Amplification of Chiral Superstructures of Carbazole Porphyrins in Dynamic Supramolecular Aggregates","authors":"Pooja V Shreechippa, Dinesh N Nadimetla, Avinash L. Puyad, Ambadas B. Rode, Sheshanath V. Bhosale","doi":"10.1002/ejoc.202401181","DOIUrl":"https://doi.org/10.1002/ejoc.202401181","url":null,"abstract":"Herein, we reported design, synthesis and investigation for supramolecular self-assembly of two types of carbazole porphyrins one with free base carbazole porphyrin (codes as 1), and second one zinc (II) metalated carbazole porphyrin (codes as 2) in the various ratios of chloroform (CHCl3, non-polar) and methanol (MeOH, polar) mixed solvent. Typically, in only chloroform both 1 and 2 produce micro-belt like structures, while increasing polar solvents i.e. 90% MeOH in CHCl3 (v/v, 9:1 ratio), 1 resulted as helical microfibres, however, 2 assembled into twisted helical ribbons, respectively. The solution based solvophobic effect on self-assembly demonstrated by using circular dichroism (CD), UV-Vis and emission spectroscopy. Furthermore, X-ray diffraction was used to confirm amorphous nature of assembly and DFT for computational study used to find energy band gap between carbazole and porphyrin. Importantly, Scanning Electron Microscopy (SEM) was employed to visualise chiral supramolecular superstructures of 1 and 2, respectively. It is clear that growth of chiral superstructures is due to π–π stacking of porphyrin core along with hydrophobic interaction of the ethyl hexyl chain. Thus, it is clear that adjusting the ratio of polar to non-polar solvent, hydrophobic carbazole porphyrins confirmed formation of chiral superstructures.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"33 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2024-12-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142821042","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
Iodine(III)‐Mediated Unexpected Ring‐contraction Rearrangement and Halogenated Addition Reaction to Synthesize 3‐Substituted Phthalides and Isochroman‐1‐one Derivatives 碘（III）介导的意外缩环重排和卤代加成反应合成 3-取代邻苯二甲酸盐和异苯并吡喃-1-酮衍生物
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2024-12-13 DOI: 10.1002/ejoc.202401173
Yang Cao, Fanjing Meng, Yihang Zhou, Wenhui Cui, Xinxin Si, Tao Liu
{"title":"Iodine(III)‐Mediated Unexpected Ring‐contraction Rearrangement and Halogenated Addition Reaction to Synthesize 3‐Substituted Phthalides and Isochroman‐1‐one Derivatives","authors":"Yang Cao, Fanjing Meng, Yihang Zhou, Wenhui Cui, Xinxin Si, Tao Liu","doi":"10.1002/ejoc.202401173","DOIUrl":"https://doi.org/10.1002/ejoc.202401173","url":null,"abstract":"Iodine(III)‐mediated ring‐contraction rearrangement and halogenated addition reaction have been realized. A series of 3‐substituted phthalides and isochroman‐1‐one derivatives bearing multiple functional groups were obtained in good to excellent yields under mild reaction conditions. Computational studies indicated that the reaction proceeds via a proton transfer followed by ring opening and ring formation to produce the target product. Moreover, preliminary biological evaluations revealed that both of 3‐substituted phthalides and isochroman‐1‐one derivatives show good antitumor activities.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"10 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2024-12-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142815788","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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