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Transition-Metal Catalyzed, Thermally Driven [2π+2π]-Cycloadditions of Olefins and Alkynes
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-02-20 DOI: 10.1002/ejoc.202401403
Dragos Adrian Rosca, Leif E. Hertwig, Felix J. Becker
{"title":"Transition-Metal Catalyzed, Thermally Driven [2π+2π]-Cycloadditions of Olefins and Alkynes","authors":"Dragos Adrian Rosca, Leif E. Hertwig, Felix J. Becker","doi":"10.1002/ejoc.202401403","DOIUrl":"https://doi.org/10.1002/ejoc.202401403","url":null,"abstract":"The [2+2]-cycloaddition of olefins and alkynes stands out as a versatile and atom-economical strategy for synthesizing cyclobutane and cyclobutene building blocks, which are challenging to access through other synthetic methods. While photochemical approaches have traditionally dominated this field, thermally-driven methods employing transition metals offer distinct advantages, including decreased reliance on pre-functionalized substrates and improved scalability. This review explores the underlying principles of metal-catalyzed [2+2]-cycloadditions and highlights recent advances in thermally-driven approaches for the efficient synthesis of cyclobutane and cyclobutene frameworks. Particular attention is given to electronically unbiased substrates, which remain a significant challenge for photochemical approaches.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"50 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-02-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143462711","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
Tandem Friedel−Crafts Alkylation/Lactonization for γ-Lactone
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-02-20 DOI: 10.1002/ejoc.202500044
Fufang Wu, Miao Liu, Hao Jia, Xueyin Zhang, Xiaobao Shen, Hongbin Zhai
{"title":"Tandem Friedel−Crafts Alkylation/Lactonization for γ-Lactone","authors":"Fufang Wu, Miao Liu, Hao Jia, Xueyin Zhang, Xiaobao Shen, Hongbin Zhai","doi":"10.1002/ejoc.202500044","DOIUrl":"https://doi.org/10.1002/ejoc.202500044","url":null,"abstract":"The lactonization of C(sp3)−H bonds from simple, readily available materials remains a significant challenge in organic synthesis. In this study, we present a tandem Friedel-Crafts Alkylation /Lactonization reaction using aromatic compounds and cyclo-anhydrides as raw materials to obtain γ-lactones under metal-free conditions. This method offers operational simplicity, broad substrate scope, and high synthetic efficiency. Furthermore, the gram scale experiment of this reaction had been conducted, and the synthesis of natural product Cytosporanone A was achieved using this method.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"16 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-02-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143462706","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
Automated and Parallel Amide Synthesis
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-02-19 DOI: 10.1002/ejoc.202401258
Tuo Jiang, Guillaume Coin, Samuele Bordi, Paula L. Nichols, Jeffrey W. Bode, Benedikt M. Wanner
{"title":"Automated and Parallel Amide Synthesis","authors":"Tuo Jiang, Guillaume Coin, Samuele Bordi, Paula L. Nichols, Jeffrey W. Bode, Benedikt M. Wanner","doi":"10.1002/ejoc.202401258","DOIUrl":"https://doi.org/10.1002/ejoc.202401258","url":null,"abstract":"Amide bonds are ubiquitous in molecules of interest such as pharmaceuticals, natural products, and agrochemicals. Over the last decades, significant efforts have been directed at developing efficient methods for the formation of this class of chemical bonds. Herein, we disclose a robust, user‐friendly approach for the efficient and rapid parallel synthesis of amide‐containing compounds, in good yield and purity. Our approach utilizes automated synthesis technologies and pre‐packed capsules containing all the necessary materials for the reaction and work‐up. Following manual addition of the amine and carboxylic acid, the reaction and product isolation is achieved automatically in a standardized, integrated manner. This methodology tolerates a wide diversity of carboxylic acids and amines (or amine salts). To accelerate discovery and rapidly create amide‐containing compound libraries, the method was miniaturized into an automated parallel synthesis format, using 96‐well plate kits, which could be beneficial to medicinal chemists.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"6 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-02-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143452317","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
Asymmetric Construction of Acyclic 1,3‐Nonadjacent Stereogenic Centers Containing a Tetrasubstituted Carbon through Diastereoselective Alkylation of Benzyl Sulfone Derivatives
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-02-19 DOI: 10.1002/ejoc.202401292
Rihaku Ojima, Azusa Kondoh, Masahiro Terada
{"title":"Asymmetric Construction of Acyclic 1,3‐Nonadjacent Stereogenic Centers Containing a Tetrasubstituted Carbon through Diastereoselective Alkylation of Benzyl Sulfone Derivatives","authors":"Rihaku Ojima, Azusa Kondoh, Masahiro Terada","doi":"10.1002/ejoc.202401292","DOIUrl":"https://doi.org/10.1002/ejoc.202401292","url":null,"abstract":"A strategy for the asymmetric construction of acyclic 1,3‐nonadjacent stereogenic centers containing a tetrasubstituted carbon has been established, which involves an enantioselective addition reaction and a subsequent chelate‐controlled diastereoselective alkylation reaction. Specifically, the enantioselective addition reaction of α‐thioacetamides with α‐phenyl‐substituted vinyl sulfones under chiral Brønsted base catalysis and the subsequent LDA‐mediated diastereoselective methylation, allylation and benzylation at the α position of the sulfonyl group of the adducts afforded the desired enantio‐enriched products having 1,3‐nonadjacent stereogenic centers containing a tetrasubstituted carbon in a highly stereoselective manner.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"1 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-02-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143452316","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
Regio‐ and stereoselective alkyl enol ether synthesis via microwave‐promoted, base‐catalysed alkyne hydroalkoxylation
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-02-19 DOI: 10.1002/ejoc.202500091
Alexis Perry, Owaen Guppy
{"title":"Regio‐ and stereoselective alkyl enol ether synthesis via microwave‐promoted, base‐catalysed alkyne hydroalkoxylation","authors":"Alexis Perry, Owaen Guppy","doi":"10.1002/ejoc.202500091","DOIUrl":"https://doi.org/10.1002/ejoc.202500091","url":null,"abstract":"The diverse reactivity presented by alkyl enol ethers underpins a wide range of synthetically significant processes. Their synthesis is often achieved by atom‐economical alkyne hydroalkoxylation (i.e., addition of an alcohol across an alkyne), either using superbasic conditions or transition metal catalysis. Unfortunately, the harsh conditions of the former approach limit substrate tolerance whilst the latter approach often requires inert, anhydrous conditions and exotic, expensive catalysts. In order to pursue more convenient, general and sustainable methodology for enol ether synthesis, we have developed microwave‐promoted alkyne hydroalkoxylation as an attractive solution. Our optimised conditions employ caesium carbonate as a mild base catalyst and the required alcohol as solvent and reagent, with reaction temperatures from 20‐150 °C and reaction times from 10‐60 minutes. We have demonstrated that the reaction shows broad tolerance of diverse substrate functionality (e.g., ester, ether, carboxylate, nitrile, nitro, halide), including examples of terminal, internal, aryl and alkyl alkynes. Greatest reactivity is observed with electron‐poor alkyne substrates, and the reaction shows near‐complete anti‐Markovnikov regioselectivity and a very strong stereochemical bias towards Z‐configured enol ether products. These observations are consistent with a polar mechanism proceeding via a vinyl anion intermediate, and we provide empirical and computation evidence in support of this.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"64 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-02-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143452318","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‐Catalyzed Tandem Cyclization for Efficient Synthesis of Quinazolinones from Indoles and amines
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-02-19 DOI: 10.1002/ejoc.202401323
Ruili Zhang, Xiaoying Liu, Zongze Long, Kaiyuan Zhang, Xianglong Chu
{"title":"Iodine‐Catalyzed Tandem Cyclization for Efficient Synthesis of Quinazolinones from Indoles and amines","authors":"Ruili Zhang, Xiaoying Liu, Zongze Long, Kaiyuan Zhang, Xianglong Chu","doi":"10.1002/ejoc.202401323","DOIUrl":"https://doi.org/10.1002/ejoc.202401323","url":null,"abstract":"In this study, we report an iodine‐catalyzed multicomponent reaction of indoles, glyoxylic acid or DMSO, and aliphatic amines to synthesize quinazolinone derivatives via oxygenation cleavage of the C=C double bonds of indoles. This method features mild conditions, high efficiency, and excellent functional group tolerance. The practicality of this approach is demonstrated through its application in synthesizing rutaecarpine and a scalable protocol for efficient quinazolinone production.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"25 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-02-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143452319","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
Influence of Pillararene‐Based Host–Guest Chemistry on the Enantioselective Synthesis of 2,3‐Dihydroquinazolinones
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-02-19 DOI: 10.1002/ejoc.202500081
Dan Zhou, Menglan Ma, Jiyong Liu, Yuhang Sheng, Peiling Zhang, Shuping Wang, Feihe Huang, Shijun Li, Zibin Zhang
{"title":"Influence of Pillararene‐Based Host–Guest Chemistry on the Enantioselective Synthesis of 2,3‐Dihydroquinazolinones","authors":"Dan Zhou, Menglan Ma, Jiyong Liu, Yuhang Sheng, Peiling Zhang, Shuping Wang, Feihe Huang, Shijun Li, Zibin Zhang","doi":"10.1002/ejoc.202500081","DOIUrl":"https://doi.org/10.1002/ejoc.202500081","url":null,"abstract":"To clarify the relationship between the host‐guest complexation and enantioselectivity of an asymmetric reaction, we studied the impacts of pillar[5]arene‐based host–guest chemistry on the asymmetric catalytic synthesis of cyclic dihydroquinazolinones from aldehydes, where the aldehydes meanwhile acted as guests. The addition of different pillar[5]arenes cannot only adjust the reactivity of the substrates but also change the enantiomeric excess of the products. The magnitude of such impacts is influenced by several factors, including the solvent, the temperature, the catalyst, the usage and kind of pillararenes, and the structure of aldehydes. When the pillararene‐substrate interactions are strong in the reaction systems, the ee variations of products are mainly decided by the guests, aldehydes, whereas the reaction activities are mainly affected by the hosts, pillar[5]arenes.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"13 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-02-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143443724","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 4H-imidazol-4-ones from α-Amino acids, and their Antioxidant Activities using Electron Transfer Methods
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-02-18 DOI: 10.1002/ejoc.202401449
Mukherjee Singh Okram, Mayanglambam Maneeta Devi, Keisham Subharani Devi, Thangjam Linda Devi, Thokchom Prasanta Singh
{"title":"Synthesis of 4H-imidazol-4-ones from α-Amino acids, and their Antioxidant Activities using Electron Transfer Methods","authors":"Mukherjee Singh Okram, Mayanglambam Maneeta Devi, Keisham Subharani Devi, Thangjam Linda Devi, Thokchom Prasanta Singh","doi":"10.1002/ejoc.202401449","DOIUrl":"https://doi.org/10.1002/ejoc.202401449","url":null,"abstract":"A novel series of 4H-imidazol-4-ones, designated as compounds 5(a–l), were synthesized from phenylalanine and tyrosine. This synthesis involved derivatization of amino acids with phenylacetyl chloride, followed by cyclocondensation with aromatic amines using PCl3 and a deep eutectic solvent as both catalyst and solvent. Amide intermediates were first produced via the Schotten-Baumann reaction. These intermediates then underwent cyclization in the presence of PCl3 and deep-eutectic solvent, leading to the formation of imidazolones as potent antioxidants. The newly synthesized compounds were evaluated for their antioxidant activities using several electron transfer-based assays, including DPPH, ABTS, FRAP, and CUPRAC. Among the tested compounds, compound 5i exhibited excellent antioxidant activity compared to the standard reference drugs, ascorbic acid and Trolox.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"66 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-02-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143435699","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 new approach towards the synthesis of imidazol‐4‐ones using α‐diazoesters and hydrazide catalysed by Cu(I) salt
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-02-18 DOI: 10.1002/ejoc.202401395
Hilal Ahmad Khan, S Naveen Kumar, Ananth Kumar R, Gruhapriya Jelakam, Chinnappan Sivasankar
{"title":"A new approach towards the synthesis of imidazol‐4‐ones using α‐diazoesters and hydrazide catalysed by Cu(I) salt","authors":"Hilal Ahmad Khan, S Naveen Kumar, Ananth Kumar R, Gruhapriya Jelakam, Chinnappan Sivasankar","doi":"10.1002/ejoc.202401395","DOIUrl":"https://doi.org/10.1002/ejoc.202401395","url":null,"abstract":"Imidazole and substituted imidazoles have drawn much attention owing to their superior biological functions. In this regard, devising a synthetic strategy to improve viability, easy to handle and more yield is challenging task for synthetic chemists. Herein we report a new synthetic strategy for the synthesis of imidazol‐4‐ones from hydrazides and α‐diazoesters using Cu(I) metal catalyst. In the absence of the Cu(I) catalyst or even utilizing any other metal catalyst, the imine bond formation between the terminal N of hydrazides and carbene was observed. Therefore, Cu(I) salt catalysis this reaction in a unique way. The reaction proceeds via the cleavage of the C‐N bond of the hydrazide followed by cyclization and yielded the expected product. We have also explored the substrate scope of our strategy and obtained excellent yields. We have isolated the products in a pure form and fully characterized using sophisticated analytical and spectroscopic techniques including single crystal X‐Ray analysis.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"29 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-02-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143435380","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 One‐Pot Two‐Step Synthesis of Phosphoryl‐Substituted 4‐Quinolones and 3‐Indolinones
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-02-18 DOI: 10.1002/ejoc.202401423
Ivan Nuzhdin, Arina Murashkina, Stanislav Bezzubov, Alexander Mitrofanov, Irina Beletskaya
{"title":"Divergent One‐Pot Two‐Step Synthesis of Phosphoryl‐Substituted 4‐Quinolones and 3‐Indolinones","authors":"Ivan Nuzhdin, Arina Murashkina, Stanislav Bezzubov, Alexander Mitrofanov, Irina Beletskaya","doi":"10.1002/ejoc.202401423","DOIUrl":"https://doi.org/10.1002/ejoc.202401423","url":null,"abstract":"In this study, we have developed an approach for the selective two‐step synthesis of phosphoryl‐substituted 4‐quinolones and phosphoryl‐substituted 3‐indolinones. This was achieved through the reaction of (3‐(2‐iodoaryl)‐3‐oxoprop‐1‐yn‐1‐yl)phosphonates with anilines followed by Cu‐catalyzed intramolecular cyclization of the intermediately formed regioisomeric enamines, which are selectively formed under neat conditions or in the presence of a gold complex as a catalyst. This method allows for the synthesis of a series of phosphoryl‐substituted 4‐quinolones and phosphoryl‐substituted 3‐indolinones in good yields.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"49 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-02-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143435403","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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