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Iodine-Assisted Regioselective C3-H Chalcogenation of 4-Phenyl Aminocoumarin: Access to Unusual Dual Selenylation of N-Substituted Derivatives
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2024-12-13 DOI: 10.1002/ejoc.202401163
Swapan Dey, Suhag Singh Sahay, Segufa Rahaman, Rwishanya Das
{"title":"Iodine-Assisted Regioselective C3-H Chalcogenation of 4-Phenyl Aminocoumarin: Access to Unusual Dual Selenylation of N-Substituted Derivatives","authors":"Swapan Dey, Suhag Singh Sahay, Segufa Rahaman, Rwishanya Das","doi":"10.1002/ejoc.202401163","DOIUrl":"https://doi.org/10.1002/ejoc.202401163","url":null,"abstract":"A simple, efficient, metal and photocatalyst-free, eco-friendly approach for the C3-H regioselective chalcogenation of 4-phenyl aminocoumarin, as well as abnormal dual selenylation of N-substituted 4-phenyl aminocoumarin, has been developed by using diphenyl dichalcogenides and iodine as support in green solvent PEG-400 under ambient temperature and aerobic condition. Furthermore, chalcogenation of 4-phenyl amino-2-pyrone has also been accomplished in similar conditions. The proposed mechanism is based on the control experiments and suggests an ionic pathway. The reaction offers a green synthetic path with a high yield, and the methodology is crucially significant due to its operational simplicity, convenient execution, scalability, and tolerance of various functional groups.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"63 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2024-12-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142821046","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
p‐Anisil as a Versatile Catalyst for the E‐to‐Z Photoisomerization of Activated Alkenes – Application in Late‐Stage Modification of Drugs and Peptides
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2024-12-12 DOI: 10.1002/ejoc.202401338
Thanh V. Q. Nguyen, Peter R. Hansen
{"title":"p‐Anisil as a Versatile Catalyst for the E‐to‐Z Photoisomerization of Activated Alkenes – Application in Late‐Stage Modification of Drugs and Peptides","authors":"Thanh V. Q. Nguyen, Peter R. Hansen","doi":"10.1002/ejoc.202401338","DOIUrl":"https://doi.org/10.1002/ejoc.202401338","url":null,"abstract":"High‐throughput experimentation was employed to discover p‐Anisil as a highly effective and versatile catalysts for the E‐to‐Z photoisomerization of cinnamic acid derivatives and other activated alkenes. This new catalytic system tolerated a number of functional groups found in medicinal chemistry. The discovery enabled the preparation of previously unknown complex Z‐alkenes in two steps directly from drugs or peptides.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"51 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2024-12-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142815792","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
Ni‐Catalyzed Synthesis of Multisubstituted Allenes via Reductive Cross‐Coupling of Propargylic Acetates with Chlorohydrosilanes
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2024-12-12 DOI: 10.1002/ejoc.202401234
Xiaohui Yan, Hong Deng
{"title":"Ni‐Catalyzed Synthesis of Multisubstituted Allenes via Reductive Cross‐Coupling of Propargylic Acetates with Chlorohydrosilanes","authors":"Xiaohui Yan, Hong Deng","doi":"10.1002/ejoc.202401234","DOIUrl":"https://doi.org/10.1002/ejoc.202401234","url":null,"abstract":"Conventional transition metal‐catalyzed cross‐coupling reactions have been developed for the synthesis of allenes using propargyl electrophiles and various nucleophiles. However, the construction of allenes through reductive cross‐coupling remains a challenging topic. This paper presents a strategy for synthesizing multisubstituted allenes through nickel‐catalyzed reductive cross‐coupling reactions. The method employs propargyl acetates and chlorosilanes to generate a range of silyl‐substituted allenes. The reaction conditions are mild, and the process exhibits high chemo‐ and regioselectivity, along with good substrate universality. Moreover, the method can be extended to chlorogermane and chlorostannane, leading to the formation of germanium or stannium substituted allenes. This study provides a useful strategy for the synthesis of multisubstituted allenes and expands the synthetic toolbox for the construction of highly functionalized molecules.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"200 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2024-12-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142809412","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 General Protocol for the Aqueous Morita-Baylis-Hillman Reaction between Cyclic Enones and 1,2-Dicarbonyl Compounds
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2024-12-11 DOI: 10.1002/ejoc.202400852
Manoel T. Rodrigues, José Claudio Serafim, Hugo Santos, João Arantes, Ana Julia Senna, Lais V. Acconcia, Albert Moyano, Fernando Coelho
{"title":"A General Protocol for the Aqueous Morita-Baylis-Hillman Reaction between Cyclic Enones and 1,2-Dicarbonyl Compounds","authors":"Manoel T. Rodrigues, José Claudio Serafim, Hugo Santos, João Arantes, Ana Julia Senna, Lais V. Acconcia, Albert Moyano, Fernando Coelho","doi":"10.1002/ejoc.202400852","DOIUrl":"https://doi.org/10.1002/ejoc.202400852","url":null,"abstract":"A general methodology for the Morita-Baylis-Hillman reaction of cycloenones and a variety of di- and tricarbonyl compounds. The methodology involves the use of a bifunctional Lewis base as catalyst in aqueous medium at room temperature. The synthetic applicability of the polyfunctionalized MBH adducts is demonstrated by the preparation of an acenaphtho[1,2-<i>b</i>]indole derivative.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"12 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2024-12-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142810157","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
Recent Advances in Sustainable Total Synthesis and Chiral Pool Strategies with Emphasis on (–)‐Sclareol in Natural Products Synthesis 以天然产品合成中的 (-)-Sclareol 为重点的可持续全合成和手性池策略的最新进展
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2024-12-11 DOI: 10.1002/ejoc.202400983
Ayyoub Selka, Abdelnasser Abidli, Lucie Schiavo, Loïc Jeanmart, Gilles Hanquet, William David Lubell
{"title":"Recent Advances in Sustainable Total Synthesis and Chiral Pool Strategies with Emphasis on (–)‐Sclareol in Natural Products Synthesis","authors":"Ayyoub Selka, Abdelnasser Abidli, Lucie Schiavo, Loïc Jeanmart, Gilles Hanquet, William David Lubell","doi":"10.1002/ejoc.202400983","DOIUrl":"https://doi.org/10.1002/ejoc.202400983","url":null,"abstract":"Starting materials for sustainable total synthesis often come from the chiral pool: carbohydrates, cyclitols, amino acids, and terpenes. In the terpene family, (–)‐sclareol has served as a sustainable, readily available, and versatile chiral building block for the synthesis of numerous natural products. (–)‐Sclareol possesses a unique structure that has consequently promoted its integration as a core framework within various structurally complex and biologically active substances, including sesquiterpenoids, diterpenoids, and sesterterpenoids. In fact, (–)‐sclareol has facilitated access to diverse synthetic key intermediates, promoting the sustainable synthesis of several natural products. Herein, a critical and comprehensive review is presented covering the recent trends in sustainable total syntheses and the chiral pool approaches with emphasis on the synthesis of natural products through diverse synthetic routes employing (–)‐sclareol as chiral educt. Additionally, newly developed catalysts and synthetic protocols using (–)‐sclareol amongst their substrates scope are also analyzed and discussed in this review.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"1 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2024-12-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142805136","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
Research Progress of Rhodium(III)‐Catalyzed C(sp2)‐H Bond Functionalization
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2024-12-11 DOI: 10.1002/ejoc.202401177
DeMao Chen, Dao-Qing Dong, Zhao-Xin Qiu, Yi-Meng Wang, Shi-Qiang Yan, Xin-Ming Xu, Zu-Li Wang
{"title":"Research Progress of Rhodium(III)‐Catalyzed C(sp2)‐H Bond Functionalization","authors":"DeMao Chen, Dao-Qing Dong, Zhao-Xin Qiu, Yi-Meng Wang, Shi-Qiang Yan, Xin-Ming Xu, Zu-Li Wang","doi":"10.1002/ejoc.202401177","DOIUrl":"https://doi.org/10.1002/ejoc.202401177","url":null,"abstract":"Over the past decade, rhodium‐catalyzed C‐H bond activation reactions have made significant progress and found broad applications in organic synthesis, biomedicine, and materials science. This is primarily attributed to their broad substrate scope, excellent functional group compatibility, and high reactivity. Currently, although considerable progress has been made, rhodium‐catalyzed C(sp2)‐H functionalization still heavily relies on directing groups to achieve selectivity, which significantly diminishes the reaction's efficiency. Additionally, the challenge of selectively functionalizing remote (meta/para) C‐H bonds further complicates research in this field. In this review, we primarily focus on the research progress in rhodium‐catalyzed C(sp2)‐H functionalization from 2018 to 2024, categorizing reactions by type and providing a systematic overview of the mechanistic insights for each.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"5 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2024-12-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142805052","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
Dehydrogenative Photoredox Catalyzed Synthesis of Indolyl Δ2‐Isoxazolines via a Formal C(sp3)–H Functionalization.
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2024-12-11 DOI: 10.1002/ejoc.202401369
Jonathan da Luz, Farhaan Dobah, James Rossi-Ashton, Richard J. Payne, William Unsworth, Wade Petersen
{"title":"Dehydrogenative Photoredox Catalyzed Synthesis of Indolyl Δ2‐Isoxazolines via a Formal C(sp3)–H Functionalization.","authors":"Jonathan da Luz, Farhaan Dobah, James Rossi-Ashton, Richard J. Payne, William Unsworth, Wade Petersen","doi":"10.1002/ejoc.202401369","DOIUrl":"https://doi.org/10.1002/ejoc.202401369","url":null,"abstract":"A dehydrogenative photoredox catalyzed formal C(sp3)‐H intramolecular cyclization of indolyl‐oximes to generate indolyl Δ2‐isoxazolines is reported. In contrast to the current state‐of‐the‐art, the reaction avoids the use of super stoichiometric chemical oxidants and high reaction temperatures and is proposed to operate via two sequential single electron oxidation events.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"37 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2024-12-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142805190","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
Advances in C-N bond Formation via N-centered Radicals from N-Aminopyridinium Reagents
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2024-12-11 DOI: 10.1002/ejoc.202401220
Tiegen Chen, farrukh sajjad, Cheng Lu
{"title":"Advances in C-N bond Formation via N-centered Radicals from N-Aminopyridinium Reagents","authors":"Tiegen Chen, farrukh sajjad, Cheng Lu","doi":"10.1002/ejoc.202401220","DOIUrl":"https://doi.org/10.1002/ejoc.202401220","url":null,"abstract":"Abstract: Nitrogen-centered radicals (NCRs) have gained significant attention due to their high reactivity, which facilitates many useful and challenging transformations, particularly in the formation of C–N bonds. In this regard, N-aminopridinium reagents are easily accessible substrates that readily generate N-centered radicals, which can be trapped by arenes, olefins, alkynes and even alkanes under visible light irradiation. In recent years, amination strategies involving N-aminopyridinium salts have grown remarkably and attracted considerable interest within the synthetic community. This review comprehensively includes all the significant advances in C–N bond construction via N-centered radicals derived from N-aminopyridinium substrates.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"21 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2024-12-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142810155","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
From Enzyme Encapsulation to Environmental Solutions: Photostable Laccase in DOPC Vesicles
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2024-12-11 DOI: 10.1002/ejoc.202400807
MARIA ALEJANDRA LUNA, Eugenia Reynoso, M. Alicia Biasutti, Hernán A. Montejano, Fernando Moyano, N. Mariano Correa
{"title":"From Enzyme Encapsulation to Environmental Solutions: Photostable Laccase in DOPC Vesicles","authors":"MARIA ALEJANDRA LUNA, Eugenia Reynoso, M. Alicia Biasutti, Hernán A. Montejano, Fernando Moyano, N. Mariano Correa","doi":"10.1002/ejoc.202400807","DOIUrl":"https://doi.org/10.1002/ejoc.202400807","url":null,"abstract":"The laccase enzyme offers significant advantages for the removal of organic contaminants; but its stability and effectiveness in bioremediation can be compromised by photo-induced degradation processes. To address this challenge, we investigated the immobilization of laccase in unilamellar and multilamellar vesicles of dioleoyl phosphatidylcholine (DOPC) as a means to enhance its photo-stability while preserving its catalytic activity. Enzymatic activity was evaluated spectroscopically for both free and encapsulated laccase, before and after UVB irradiation.\u0000Our results demonstrate that DOPC vesicles effectively encapsulate the laccase enzyme, maintaining its activity within the vesicles. Moreover, the substrate syringaldazine, a model compound for laccase activity studies, was able to permeate through the bilayer. Notably, encapsulated laccase exhibited significantly higher retention of enzymatic activity (REA) post-irradiation compared to the free enzyme.\u0000In conclusion, both unilamellar and multilamellar vesicles provide substantial photoprotection for laccase against UVB light. This protective effect is attributed to the enzyme's confinement within a system that scatters high-energy photons. Furthermore, the simplicity and ease of large-scale production of multilamellar vesicles present an advantageous option for various applications, including bioremediation.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"8 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2024-12-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142805050","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 Oxidative Hydroxychalcogenation of Olefins with Disulfides/Thiols/Diselenides and H2O as Nucleophilic Oxygen Sources 以二硫化物/硫醇/二硒化物和 H2O 为亲核氧源的烯烃电化学氧化羟基钙化反应
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2024-12-11 DOI: 10.1002/ejoc.202401226
Wenxue Li, Junwu Li, Fengkai Sun, Man Miao, Xiao-Bing Lan, Jian-Qiang Yu, Pengpeng Liu, Houyuan Li, Rui Wang, Jian Zhang, Zhenyu An
{"title":"Electrochemical Oxidative Hydroxychalcogenation of Olefins with Disulfides/Thiols/Diselenides and H2O as Nucleophilic Oxygen Sources","authors":"Wenxue Li, Junwu Li, Fengkai Sun, Man Miao, Xiao-Bing Lan, Jian-Qiang Yu, Pengpeng Liu, Houyuan Li, Rui Wang, Jian Zhang, Zhenyu An","doi":"10.1002/ejoc.202401226","DOIUrl":"https://doi.org/10.1002/ejoc.202401226","url":null,"abstract":"A direct electrochemical redox reaction of olefins and disulfides/thiols/diselenides without external oxidants has been developed, which includes the hydroxychalcogenation of olefins. This procedure exhibited good functional group tolerance, and a series of β‐hydroxysulfide/β‐hydroxyselenide derivatives were obtained in moderate to good yields. Mechanistic studies and cyclic voltammetry were also conducted to elucidate the reaction process.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"28 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2024-12-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142805137","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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