European Journal of Organic Chemistry最新文献_第5页

Mechanochemical Dissociation of Singlet Carbene–CS2 Adducts 单重态碳cs2加合物的机械化学解离

IF 2.5 3区化学

European Journal of Organic Chemistry Pub Date : 2025-04-23 DOI: 10.1002/ejoc.202500004

Gayeong Lim , Subin Park , Minji Lee , Dongmin Kang , Prof. Dr. Youngsuk Kim

{"title":"Mechanochemical Dissociation of Singlet Carbene–CS2 Adducts","authors":"Gayeong Lim , Subin Park , Minji Lee , Dongmin Kang , Prof. Dr. Youngsuk Kim","doi":"10.1002/ejoc.202500004","DOIUrl":"10.1002/ejoc.202500004","url":null,"abstract":"<div><div>Owing to the extensive application of singlet carbenes, their generation through the release of small molecules from stable adducts is attracting increasing research interest. This study explores the mechanochemical release of CS2 from Carbene–CS2 adducts formed by three distinct singlet carbenes: cyclic (alkyl)(amino)carbene (CAAC); N‐heterocyclic carbene (NHC); and N,N’‐diamidocarbene (DAC). Under ball‐milling conditions, these adducts exhibit notably different reactivities; DAC–CS2 releases CS2 completely within 20 min, NHC–CS2 has a slower release rate, while CAAC–CS2 decomposes into a complex mixture. DFT calculations reveal that the release of CS2 from CAAC–CS2 requires the highest activation energy (32 kcal/mol), suggesting that it is inaccessible under the reaction conditions. This is likely because of the higher HOMO energy of CAAC, which correlates with a stronger bond with CS2, thereby limiting its dissociation. This study highlights how the electronic structures of carbenes influence their interactions with small molecules, paving the way for controlling the reactivity of carbene–small‐molecule adducts.</div></div>","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"28 16","pages":"Article e202500004"},"PeriodicalIF":2.5,"publicationDate":"2025-04-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143470688","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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NHC‐Organocatalyzed Multicomponent Fluorination and Fluoroalkylation for Access to Fluorine‐Containing Compounds nhc有机催化多组分氟化和氟烷基化制备含氟化合物

IF 2.5 3区化学

European Journal of Organic Chemistry Pub Date : 2025-04-23 DOI: 10.1002/ejoc.202401473

Jie Lv , Ziliang Yuan , Xinyan Yang , Xuning Qiu , Yimeng Yang , Yanrong Ren

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Regioselective Synthesis of n‐Nonanal and Aldehyde‐Containing Polysiloxanes via Rh‐Catalyzed Hydroformylation Enhanced by A New Silicon‐Tethered Multidentate Phosphine Ligand 一种新型硅系多齿膦配体增强的Rh催化氢甲酰化合成正壬醛和含醛聚硅氧烷的区域选择性

IF 2.5 3区化学

European Journal of Organic Chemistry Pub Date : 2025-04-23 DOI: 10.1002/ejoc.202500020

Shu‐Yuan Tian , Lin Shi , Jun‐Hui Zhu , Dr. Li Li , Dr. Fei Ye , Prof. Dr. Zheng Xu , Prof. Dr. Li‐Wen Xu

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Photochemical Multicomponent Synthesis of Six‐Membered Heterocycles 六元杂环的光化学多组分合成

IF 2.5 3区化学

European Journal of Organic Chemistry Pub Date : 2025-04-23 DOI: 10.1002/ejoc.202401480

Dr. Biplob Borah , Mihir Patat , Dr. L. Raju Chowhan

{"title":"Photochemical Multicomponent Synthesis of Six‐Membered Heterocycles","authors":"Dr. Biplob Borah , Mihir Patat , Dr. L. Raju Chowhan","doi":"10.1002/ejoc.202401480","DOIUrl":"10.1002/ejoc.202401480","url":null,"abstract":"<div><div>Despite the efficient progress achieved in the synthesis of heterocyclic compounds, accessing these molecules by combining both visible lights induced radical chemistry and multicomponent reactions is extremely demanding yet challenging. Recognizing the significant features associated with oxygen‐ and nitrogen‐containing heterocyclic compounds, the search for these attractive molecules in nature and developing new synthetic strategies for synthesizing these molecules remain interesting domain for synthetic chemists. In this mini‐review article, we aim to demonstrate a transitory outline of the recent development achieved in the synthesis of six‐membered heterocycles having oxygen and nitrogen as the major heteroatoms as well as six‐membered heterocycle containing spirooxindole molecules based on visible‐light‐induced photochemical multicomponent reactions strategies. Besides addressing the key success of the reaction design and product developments in this promising area, we have also emphasized the major shortcomings and challenges associated with the reaction discovery in order to stimulate further succeeding investigations.</div></div>","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"28 16","pages":"Article e202401480"},"PeriodicalIF":2.5,"publicationDate":"2025-04-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143599704","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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Blue‐Light‐Induced Stereoselective Synthesis of α‐Alkylated Amino Acid Derivatives 蓝光诱导 α-烷基化氨基酸衍生物的立体选择性合成

IF 2.5 3区化学

European Journal of Organic Chemistry Pub Date : 2025-04-23 DOI: 10.1002/ejoc.202401477

Hongying Fan , Meiling Ye , Xue Zhang , Jinyu Hou , Liulin Jiao , Jian Chen , Li Guo , Zhong Lian , Yong Wu

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Photoinduced Copper-Catalyzed N-Arylation Reaction of N–H Heteroarenes Using Aryl Thianthrenium Salts 利用芳基硫鎓盐光诱导N-H杂芳烃的n -芳基化反应

IF 2.8 3区化学

European Journal of Organic Chemistry Pub Date : 2025-04-22 DOI: 10.1002/ejoc.202500303

Zhenhui Wang, Qianqian Yang, Lan Bao, Ruiyun Zhang, Mingming Gao, wei liu

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Tagitinin C, a Sesquiterpene Lactone, and Derivatives as Proteasome Inhibitors 倍半萜内酯及其衍生物作为蛋白酶体抑制剂

IF 2.8 3区化学

European Journal of Organic Chemistry Pub Date : 2025-04-22 DOI: 10.1002/ejoc.202500181

Georges Massiot, Fadila Derguini, Flavien Marcadet, Fabien Plisson, Raphael Rahmani, Florie Lavigne, Christophe Menendez, Christophe Long

{"title":"Tagitinin C, a Sesquiterpene Lactone, and Derivatives as Proteasome Inhibitors","authors":"Georges Massiot, Fadila Derguini, Flavien Marcadet, Fabien Plisson, Raphael Rahmani, Florie Lavigne, Christophe Menendez, Christophe Long","doi":"10.1002/ejoc.202500181","DOIUrl":"https://doi.org/10.1002/ejoc.202500181","url":null,"abstract":"Tagitinin C, a germacranolide, isolated from Tithonia diversifolia was shown to have an interesting level of activity on the proteasome pathway. It is however a particularly unstable molecule, sensitive to acids, bases, nucleophiles, and light. This article describes a series of modifications aimed at improving the chemical and biological properties of the molecule and securing a solid industrial property. This study particularly focuses on the isobutyrate chain replacement by other esters or ethers. The key steps were the cross-conjugated dienone reactivity neutralization by reduction and the methylene lactone protection with morpholine or imidazole. Selective saponification of the isobutyrate was also achieved with crude pig liver esterase leading to tagitinol C with a moderate yield. Heliangine from the Jerusalem artichoke (Helianthus tuberosus) and hydroxylated derivatives of tagitinin C from the common sunflower (Helianthus annuus), two abundant field crops, constituted alternative sources of germacranolide derivatives not accessible from tagitinin C. Some esters were more potent than the lead compound, whereas the di-ethers displayed higher activity levels, probably due to a better in vivo stability.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"2 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-04-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143858150","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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Front Cover: Investigations into Intramolecular Cerium- and Manganese-Catalyzed Aerobic Coupling of β-Oxoesters with Styryl Moieties (Eur. J. Org. Chem. 15/2025) 封面：分子内铈和锰催化β-氧酯与苯乙烯基部分的好氧偶联的研究。j . Org。化学15/2025)

IF 2.5 3区化学

European Journal of Organic Chemistry Pub Date : 2025-04-22 DOI: 10.1002/ejoc.202581501

M.Sc. Julian Friedrich, Dr. Marc Schmidtmann, Prof. Dr. Jens Christoffers

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Ring-Rearrangement-Driven Formal (3+2) Cycloaddition of Enaminone-Based Thioalkynes with Nitriles to Form Thiazole-Containing Bis-heterocycles 烯酮基硫代炔与腈形成含噻唑的双杂环的环重排驱动的正式（3+2）环加成反应

IF 2.8 3区化学

European Journal of Organic Chemistry Pub Date : 2025-04-22 DOI: 10.1002/ejoc.202500287

Chandran R, Abha Sharma, Keshri Nath Tiwari

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New Glycoconjugates Containing Selenium and Polyphenols. Stereoselective Synthesis by Pummerer-like Rearrangement 含硒和多酚的新糖缀合物。类振子重排立体选择性合成

IF 2.8 3区化学

European Journal of Organic Chemistry Pub Date : 2025-04-19 DOI: 10.1002/ejoc.202500291

Claudia González, Mauro De Nisco, Reinier Lemos, Giovanna Cimmino, Yoana Pérez-Badell, Severina Pacifico, Silvana Pedatella

{"title":"New Glycoconjugates Containing Selenium and Polyphenols. Stereoselective Synthesis by Pummerer-like Rearrangement","authors":"Claudia González, Mauro De Nisco, Reinier Lemos, Giovanna Cimmino, Yoana Pérez-Badell, Severina Pacifico, Silvana Pedatella","doi":"10.1002/ejoc.202500291","DOIUrl":"https://doi.org/10.1002/ejoc.202500291","url":null,"abstract":"In the last 20 years the exploitation of antioxidant activity of selenobased compounds has improved, just due to the use of Ebselen, a selenocompound, as a Glutathione peroxidase (GPx) mimic. However, their clinical use seems to be compromised by the low solubility in water. To deal with this problem is possible to take advantage of the new approach including selenosugars in which selenium replaces heterocyclic oxygen. In this frame, to optimize the antioxidant properties of selenosugars, the glycoconjugation with a polyphenolic unit, which is a molecule capable of inhibiting or disabling the action of free radicals, has been considered in this work. The Mitsunobu reaction mechanism links covalently the primary alcoholic function of selenobased glycosyl donors, coming from the commercially available d-mannose, and phenolic moiety acceptors, to obtain the corresponding glycoconjugates, has been exploited affording the products in efficient yields. A DFT theoretical study was carried out to help understand the possible influence of the seleno donor on the reactivity. Crucially, a new pathway based on Pummerer-like rearrangement followed by a glycosylation, gave a selenosugar with selenium in the ring and bearing an acetal-like functional group at C-1. All compounds were characterized by NMR spectroscopy confirming their structures and purity.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"28 7 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-04-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143849458","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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