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Photochemical‐, Electrochemical‐, and Photoelectrochemical‐ Catalyzed Hydrogen Atom Transfer from Aldehydes to Acyl Radicals and Their Transformations 光化学、电化学和光电化学催化的氢原子从醛到酰基自由基的转移及其转化
IF 2.5 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-02-10 DOI: 10.1002/ejoc.202401206
Dr. Fang Wang , Dr. Bin Wang , Qidi Wang , Prof. Dr. Lei Wang
{"title":"Photochemical‐, Electrochemical‐, and Photoelectrochemical‐ Catalyzed Hydrogen Atom Transfer from Aldehydes to Acyl Radicals and Their Transformations","authors":"Dr. Fang Wang ,&nbsp;Dr. Bin Wang ,&nbsp;Qidi Wang ,&nbsp;Prof. Dr. Lei Wang","doi":"10.1002/ejoc.202401206","DOIUrl":"10.1002/ejoc.202401206","url":null,"abstract":"<div><div>Acyl radical has assumed an eminent position in the synthetic chemistry due to its unique and often highly reactivity. Using aldehyde as acyl radical source does not require the prefunctionalization of substrate. Furthermore, the formation of acyl radical can be achieved through a hydrogen atom transfer (HAT) process. In recent years, photochemical‐, electrochemical‐, and photoelectrochemical‐catalyzed intermolecular HAT from aldehydes have been regarded as mild and sustainable routes to acyl radicals. Herein, we discuss the important advancements in the past 6 years in photo‐, electro‐, and photoelectro‐catalyzed generation of acyl radicals from aldehydes and their applications in organic synthesis. We also highlight the mechanistic insights that have emerged from these transformations.</div></div>","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"28 6","pages":"Article e202401206"},"PeriodicalIF":2.5,"publicationDate":"2025-02-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142805049","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: Divergent Synthesis of 4-Aminotriazoles Through Click Cycloaddition and Generation of Iodonium(III) Triazoles (Eur. J. Org. Chem. 6/2025)
IF 2.5 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-02-10 DOI: 10.1002/ejoc.202580601
Takumi Hayashi, Elghareeb E. Elboray, Hina Sudo, Naoko Takenaga, Hiroyuki Satake, Toshifumi Dohi
{"title":"Front Cover: Divergent Synthesis of 4-Aminotriazoles Through Click Cycloaddition and Generation of Iodonium(III) Triazoles (Eur. J. Org. Chem. 6/2025)","authors":"Takumi Hayashi,&nbsp;Elghareeb E. Elboray,&nbsp;Hina Sudo,&nbsp;Naoko Takenaga,&nbsp;Hiroyuki Satake,&nbsp;Toshifumi Dohi","doi":"10.1002/ejoc.202580601","DOIUrl":"https://doi.org/10.1002/ejoc.202580601","url":null,"abstract":"<p><b>The Front Cover</b> illustrates the coupling of iodonium(III) triazoles with amines through copper catalysis. 1,2,3-Triazolyliodonium(III) salts are demonstrated to be a valuable synthetic tool for the transfer of triazoles. Just as kingfishers target prey and skillfully catch small fish with their beaks, these compounds exhibit efficient reactivity with amines to produce 4-aminotriazoles. More information can be found in the Research Article by T. Dohi and co-workers (DOI: 10.1002/ejoc.202401273). Artwork by Takumi Hayashi.\u0000 <figure>\u0000 <div><picture>\u0000 <source></source></picture><p></p>\u0000 </div>\u0000 </figure>\u0000 </p>","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"28 6","pages":""},"PeriodicalIF":2.5,"publicationDate":"2025-02-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/ejoc.202580601","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143380196","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Recent Advances in Zinc-Catalyzed Carbon-Heteroatom Bond Formation
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-02-10 DOI: 10.1002/ejoc.202401271
Julio Álvarez-Valle, Patricia García-Martínez, Luis A. López, Javier Santamaría
{"title":"Recent Advances in Zinc-Catalyzed Carbon-Heteroatom Bond Formation","authors":"Julio Álvarez-Valle, Patricia García-Martínez, Luis A. López, Javier Santamaría","doi":"10.1002/ejoc.202401271","DOIUrl":"https://doi.org/10.1002/ejoc.202401271","url":null,"abstract":"Zinc has been an overlooked metal in catalysis for many years. However, this situation has begun to change in the last two decades with a number of contributions demonstrating that zinc salts and complexes are able to catalyze transformations typically accomplished with catalysts based on precious transition metals. The development of such zinc-catalyzed methodologies is highly appealing because, in general, zinc catalysts are easily available, inexpensive and less toxic. This Review aims to present the most recent and relevant examples of the use of zinc catalysts in the formation of carbon-heteroatom bonds, which is a very important process in synthetic organic chemistry.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"144 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-02-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143375486","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
Photolabile ortho‐Nitro‐Benzyl Carbonate as an Amino Protecting Group for Stereocontrolled Synthesis of 2‐Amino‐2‐Deoxy‐β‐d‐Glycosides 可发光的邻硝基苄基碳酸酯作为氨基保护基用于 2-氨基-2-脱氧-β-D-糖苷的立体控制合成
IF 2.5 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-02-10 DOI: 10.1002/ejoc.202401160
Jintao Shang , Yi Wang , Dongsheng Chang , Jibin Zheng , Hongyu Chen , Shuang Yao , Prof. Dr. You Yang
{"title":"Photolabile ortho‐Nitro‐Benzyl Carbonate as an Amino Protecting Group for Stereocontrolled Synthesis of 2‐Amino‐2‐Deoxy‐β‐d‐Glycosides","authors":"Jintao Shang ,&nbsp;Yi Wang ,&nbsp;Dongsheng Chang ,&nbsp;Jibin Zheng ,&nbsp;Hongyu Chen ,&nbsp;Shuang Yao ,&nbsp;Prof. Dr. You Yang","doi":"10.1002/ejoc.202401160","DOIUrl":"10.1002/ejoc.202401160","url":null,"abstract":"<div><div>Traditional amino protecting groups are often removed under harsh conditions or incompatible with other protecting groups, rendering the synthesis of complex 2‐amino‐2‐deoxy‐β‐<span>d</span>‐glycosides difficult. Here, we utilize the photolabile <em>ortho</em>‐nitrobenzyl carbonate (<em>o</em>NBC) as an amino protecting group for stereocontrolled synthesis of 2‐amino‐2‐deoxy‐β‐<span>d</span>‐glycosides. The gold(I)‐catalyzed glycosylation with per‐<em>O</em>‐<em>o</em>NBC‐protected 2‐<em>N</em>‐phthaloyl (Phth)‐2‐deoxy‐, 2‐<em>N</em>‐trichloroacetyl (TCA)‐2‐deoxy‐, and 2‐<em>N‐o</em>NBC‐2‐deoxy‐glycosyl ynenoates proceeded smoothly to provide 2‐amino‐2‐deoxy glycosides with exclusive β‐selectivities via the neighboring group participation (NGP) effect. Removal of the multiple <em>O</em>‐ and <em>N</em>‐<em>o</em>NBC protecting groups of 2‐amino‐2‐deoxy glycosides was achieved under irradiation at 365 nm with aminomethyl polystyrene as the carbonyl scavenger.</div></div>","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"28 6","pages":"Article e202401160"},"PeriodicalIF":2.5,"publicationDate":"2025-02-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142691025","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 on Light-Mediated Nitrene Transfer Reactions: An Emerging Area
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-02-10 DOI: 10.1002/ejoc.202401404
Minghan Yao, Gang Chen, Xinke Zhang, Abdulla Yusuf, Xinfang Xu
{"title":"Recent Advances on Light-Mediated Nitrene Transfer Reactions: An Emerging Area","authors":"Minghan Yao, Gang Chen, Xinke Zhang, Abdulla Yusuf, Xinfang Xu","doi":"10.1002/ejoc.202401404","DOIUrl":"https://doi.org/10.1002/ejoc.202401404","url":null,"abstract":"Nitrogen atoms are fundamental in biological systems and are widely found in approved drugs, natural products, and materials. Thus, catalytic methods for the C-N bond formation have attracted significant attention in synthetic chemistry. Among the toolbox, nitrene transfer reaction is one of the powerful protocols for the construction of N-incorporating frameworks with structural diversity. In this field, transition metal-catalyzed nitrene transfer reactions have been extensively explored using different types of precursors. On the other hand, photochemistry offers a sustainable protocol in synthetic chemistry, which has emerged as an eco-friendly catalytic method in nitrene chemistry, particularly, with the induction of visible light as the initiator in this area. In the last decade, a variety of visible-light-mediated synthetic transformations involving free nitrene species have been reported under mild reaction conditions. Thus, it is timely and highly desirable to summarize the advancements in this area. This review summarized the advances in photo-mediated nitrene transfer reactions from 1950s to 2024, which is organized into two sections according to the protocols for the nitrene formation: (i) direct photolysis of diverse nitrene precursors and (ii) photocatalytic generation of free nitrenes. The detailed reaction mechanisms and synthetic potential are the main focus in this review article.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"29 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-02-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143385879","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
Water Mediated Chemoselective Synthesis of Novel Spiro benzoxazinoindoline and Extended Synthesis of Spiro benzoxazinoindene Derivatives*
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-02-10 DOI: 10.1002/ejoc.202401488
Diksha Bansal, Pooja Sivaganesan, Chibisree Elanchezhian, Gokulprasanth Nataraj, Mrinal Kanti Das, Saikat Chaudhuri
{"title":"Water Mediated Chemoselective Synthesis of Novel Spiro benzoxazinoindoline and Extended Synthesis of Spiro benzoxazinoindene Derivatives*","authors":"Diksha Bansal, Pooja Sivaganesan, Chibisree Elanchezhian, Gokulprasanth Nataraj, Mrinal Kanti Das, Saikat Chaudhuri","doi":"10.1002/ejoc.202401488","DOIUrl":"https://doi.org/10.1002/ejoc.202401488","url":null,"abstract":"Spirobenzoxazines are a unique class of heterocyclic compounds that combine the structural features of spiro and benzooxazine frameworks, offering enhanced chemical stability and diverse biological activities. Their rigid three-dimensional structures make them ideal candidates for interacting with biological targets, contributing to their potential in various therapeutic applications, including anticancer, antimicrobial, and enzyme inhibition. However, the development of efficient and sustainable methods for the synthesis of spirobenzoxazines remains a challenge in organic synthesis. In this work, we present a novel and environmentally friendly approach for the synthesis of spirobenzoxazine derivatives. Utilizing water as a green solvent, this methodology offers an efficient and sustainable route for constructing these complex heterocyclic frameworks. By emphasizing eco-friendly practices, this approach aligns with the principles of green chemistry, providing both high yields and operational simplicity. This advancement not only highlights the potential of spirobenzoxazines in the pharmaceutical and material sciences but also paves the way for future research in sustainable synthetic methodologies.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"4 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-02-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143385897","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
Catalytic Asymmetric Azidative Functionalization of Alkenes
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-02-10 DOI: 10.1002/ejoc.202500015
Fuming Zhong, Xiaodan Zhao, Lihao Liao
{"title":"Catalytic Asymmetric Azidative Functionalization of Alkenes","authors":"Fuming Zhong, Xiaodan Zhao, Lihao Liao","doi":"10.1002/ejoc.202500015","DOIUrl":"https://doi.org/10.1002/ejoc.202500015","url":null,"abstract":"Aliphatic azides are an important class of nitrogen-containing compounds found in numerous biologically active molecules. Besides, they also serve as useful building blocks owning to their remarkable reactivities. Catalytic azidation of alkenes is an efficient way to produce aliphatic azides. In this respect, azidated chiral molecules can be formed if a chiral catalyst is used. The last quarter of century has witnessed a burgeoning of new methods for catalytic enantioselective azidative functionalization of alkenes to yield chiral alkyl azides. In this review, we provide a summary of the development of the asymmetric azidation of alkenes systematically, from the view of reaction models (conjugate addition, π activation, reductive elimination, and radical addition and atom transfer) combining the roles that azido sources play (nucleophilic, electrophilic, and radical). This review will be useful to the fields of azide chemistry and asymmetric alkene functionalization.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"57 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-02-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143385881","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
β‐halovinyl Aldehydes: Multifaceted Versatile Building Blocks In Organic Synthesis β-卤乙烯基醛：有机合成中的多面多用途构建块
IF 2.5 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-02-10 DOI: 10.1002/ejoc.202401058
Paras Saini , Jyoti , Pawan K. Sharma , Virender Singh
{"title":"β‐halovinyl Aldehydes: Multifaceted Versatile Building Blocks In Organic Synthesis","authors":"Paras Saini ,&nbsp;Jyoti ,&nbsp;Pawan K. Sharma ,&nbsp;Virender Singh","doi":"10.1002/ejoc.202401058","DOIUrl":"10.1002/ejoc.202401058","url":null,"abstract":"<div><div>β‐halovinyl aldehydes serve as a valuable building blocks in organic synthesis. These aldo‐x bifunctional building blocks (AXB3s) contain a alkenic double bond (vinyl) as well as a formyl group along with a halogen atom (Cl, Br, I) bonded with the β‐carbon atom of vinyl aldehyde. Owing to the presence of these multiple reactive sites, β‐halovinyl aldehydes act as a suitable precursor for Michael addition, direct addition, addition‐elimination reactions, cross‐coupling reactions, condensation reactions, nucleophilic substitution reactions, domino reactions, MCRs, Diels‐Alder reaction, functional group transformation reactions and enantioselective transformations. Therefore, a comprehensive review on synthetic exploration of β‐halovinyl aldehydes has been carried out for the generation of reactive intermediates and diverse bioactive heterocycles by using various C−C, C−N, C−S and C−O bond forming reactions. In this review, we have assembled the literature from mid‐2007 to Jan 2024.</div></div>","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"28 6","pages":"Article e202401058"},"PeriodicalIF":2.5,"publicationDate":"2025-02-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142797818","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 n -氨基吡啶试剂中n中心自由基形成C-N键的研究进展
IF 2.5 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-02-10 DOI: 10.1002/ejoc.202401220
Farrukh Sajjad , Cheng Lu , Tie‐Gen Chen
{"title":"Advances in C−N Bond Formation via N‐Centered Radicals from N‐Aminopyridinium Reagents","authors":"Farrukh Sajjad ,&nbsp;Cheng Lu ,&nbsp;Tie‐Gen Chen","doi":"10.1002/ejoc.202401220","DOIUrl":"10.1002/ejoc.202401220","url":null,"abstract":"<div><div>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, <em>N</em>‐aminopridinium reagents are easily accessible substrates that readily generate <em>N</em>‐centered radicals, which can be trapped by arenes, olefins, alkynes and even alkanes under visible light irradiation. In recent years, amination strategies involving <em>N</em>‐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 <em>N</em>‐centered radicals derived from <em>N</em>‐aminopyridinium substrates.</div></div>","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"28 6","pages":"Article e202401220"},"PeriodicalIF":2.5,"publicationDate":"2025-02-10","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
Multicomponent Modular Synthesis of Thioacetals by Using Dichloromethane as the C1 Synthon Under Mild Conditions 温和条件下以二氯甲烷为C1合成物多组份合成硫缩醛的研究
IF 2.5 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-02-10 DOI: 10.1002/ejoc.202401222
Meng‐Jun Xie , Li‐Hua Wen , Xuan Li , Ming‐Yan Chen , Yu‐Bing Li , Dr. Hai‐Dong Xia
{"title":"Multicomponent Modular Synthesis of Thioacetals by Using Dichloromethane as the C1 Synthon Under Mild Conditions","authors":"Meng‐Jun Xie ,&nbsp;Li‐Hua Wen ,&nbsp;Xuan Li ,&nbsp;Ming‐Yan Chen ,&nbsp;Yu‐Bing Li ,&nbsp;Dr. Hai‐Dong Xia","doi":"10.1002/ejoc.202401222","DOIUrl":"10.1002/ejoc.202401222","url":null,"abstract":"<div><div>Thioacetals are an important category of sulfur‐containing compounds and versatile building blocks. Therefore, there is growing demand for the development of practical and modular methods to access various thioacetals from inexpensive and readily available commodity chemicals. Herein, we describe a novel one‐pot multicomponent protocol for thioacetals synthesis, especially benzylthio thioacetals synthesis, by employing feedstock chemical dichloromethane (DCM) as the C1 source under metal‐free, mild and simple conditions. Furthermore, its synthetic utility is further demonstrated by the preparation of deuterated thioacetals, large‐scale synthesis and broad functional group compatibility. Preliminary mechanistic studies indicate the dual roles of DBU as both a proton scavenger and a nucleophilic catalyst. This work provides not only an excellent complementary strategy to the established thioacetals synthesis, but also a new platform for DCM application.</div></div>","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"28 6","pages":"Article e202401222"},"PeriodicalIF":2.5,"publicationDate":"2025-02-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142904939","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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