European Journal of Organic Chemistry最新文献_第3页

Reversible Stannylenoid Formation from the Corresponding Stannylene and Sodium Phosphaethynolate 由相应的锡炔和磷酸乙酯钠形成可逆的类锡炔

IF 2.5 3区化学

European Journal of Organic Chemistry Pub Date : 2025-04-23 DOI: 10.1002/ejoc.202500002

Yunqing Zhao , Huiyun Ma , Yanxue Bi , Jianghao Ren , Chenting Yan , Gaofeng Bian , Zhifang Li

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Cu‐catalyzed Bilateral Linkage of Sulfenamides for the Construction of Benzothiophene‐based Cyclic Sulfilimines 铜催化的双侧亚砜胺键构建环亚砜胺

IF 2.5 3区化学

European Journal of Organic Chemistry Pub Date : 2025-04-23 DOI: 10.1002/ejoc.202401467

Xinyu Zhang , Rutian Sun , Daming Zeng , Prof. Dr. Ming Wang , Prof. Dr. Xuefeng Jiang

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Pincer Ligand Facilitated Metal‐Catalyzed Multicomponent Reactions 钳形配体促进金属催化的多组分反应

IF 2.5 3区化学

European Journal of Organic Chemistry Pub Date : 2025-04-23 DOI: 10.1002/ejoc.202401469

Zi‐Qi Tian , Ying Zhang , Man‐Bo Li

{"title":"Pincer Ligand Facilitated Metal‐Catalyzed Multicomponent Reactions","authors":"Zi‐Qi Tian , Ying Zhang , Man‐Bo Li","doi":"10.1002/ejoc.202401469","DOIUrl":"10.1002/ejoc.202401469","url":null,"abstract":"<div><div>Multicomponent reactions hold a significant position in the field of organic synthetic chemistry as they can rapidly construct structurally diverse molecules with high atom economy. Pincer ligands possess unique structural and electronic properties, exhibiting remarkable catalytic activity and selectivity in multicomponent reactions. This review systematically elaborates on the research progress of multicomponent reactions involving pincer ligands, thoroughly discussing their mechanism of action in different reaction systems, including crucial aspects such as substrate activation modes, the formation and transformation of reaction intermediates. Meanwhile, an in‐depth analysis of the relationship between the structures of various pincer ligands and their reaction performance is carried out, and multiple representative reaction examples are presented, such as multicomponent transformation processes of carbon‐carbon bond and carbon‐nitrogen bond formation reactions catalyzed by metal‐pincer complexes or metal‐pincer nanoclusters. Furthermore, the future development of multicomponent reactions involving pincer ligands are prospected. It is anticipated that they will play a more crucial role in the development of novel organic synthetic methodologies, drug synthesis, and materials science, providing valuable references and inspiration for researchers in related fields.</div></div>","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"28 16","pages":"Article e202401469"},"PeriodicalIF":2.5,"publicationDate":"2025-04-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143600031","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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Catalytic Asymmetric Addition and Substitution Reactions with Grignard Reagents: Do We Know It All? 催化不对称加成和取代反应与格氏试剂：我们知道这一切吗？

IF 2.5 3区化学

European Journal of Organic Chemistry Pub Date : 2025-04-23 DOI: 10.1002/ejoc.202401457

Siriphong Somprasong , Juana M. Pérez , Marta Castiñeira Reis

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Catalytic Reactions of Alkynyl Sulfides: Versatile Tools in Synthetic Chemistry 烷基硫化物的催化反应：合成化学的通用工具

IF 2.5 3区化学

European Journal of Organic Chemistry Pub Date : 2025-04-23 DOI: 10.1002/ejoc.202401475

Wenkui Lu , Yao Yuan , Rong Jia , Gangguo Zhu

{"title":"Catalytic Reactions of Alkynyl Sulfides: Versatile Tools in Synthetic Chemistry","authors":"Wenkui Lu , Yao Yuan , Rong Jia , Gangguo Zhu","doi":"10.1002/ejoc.202401475","DOIUrl":"10.1002/ejoc.202401475","url":null,"abstract":"<div><div>Alkynyl sulfides, a significant class of heteroatom‐substituted alkynes, have garnered considerable attention within the synthetic community because of their distinctive characteristics, such as the enhanced reactivity, precise selectivity control, and facile derivatization via C−S bond couplings. Their transformations can provide a direct access to functionalized organosulfur and even sulfur‐free compounds in a highly regio‐ and stereoselective manner, which is very attractive for many fields, including organic synthesis, material science, medicinal chemistry, and life science. This review summarizes the recent progresses on catalytic reactions of alkynyl sulfides, such as the transition‐metal‐catalyzed controllable functionalizations, including hydro‐, hetero‐, and carbofunctionalizations, electrophilic additions, radical addition‐initiated functionalizations, and formal [2+n] cycloadditions, in which the reaction mechanism, selectivity control, scope and limitations are discussed in detail. Given the rapidly increasing interests and applications of sulfur‐containing compounds in both chemistry and life science, it can be anticipated that this review will be valuable for synthetic chemists and may contribute further development of the alkynyl sulfide chemistry.</div></div>","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"28 16","pages":"Article e202401475"},"PeriodicalIF":2.5,"publicationDate":"2025-04-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143385092","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

Stereoselective Strategies for the Synthesis of Functionalized Cis‐Hydrindanes in Natural Product Synthesis 天然产物合成中官能化顺式苯胺合成的立体选择策略

IF 2.5 3区化学

European Journal of Organic Chemistry Pub Date : 2025-04-23 DOI: 10.1002/ejoc.202500006

Vijayanand U. Survase , Kishor L. Handore

{"title":"Stereoselective Strategies for the Synthesis of Functionalized Cis‐Hydrindanes in Natural Product Synthesis","authors":"Vijayanand U. Survase , Kishor L. Handore","doi":"10.1002/ejoc.202500006","DOIUrl":"10.1002/ejoc.202500006","url":null,"abstract":"<div><div>The <em>cis</em>‐hydrindane motif is a bicyclic structure commonly found in many natural products that exhibit significant biological activity. This structural feature is present in a variety of bioactive compounds, particularly terpenoids, steroids, and alkaloids, which are known for their therapeutic potential, including anti‐inflammatory, antimicrobial, antiviral, and anticancer properties. Due to its prevalence and biological relevance, the <em>cis</em>‐hydrindane framework has attracted considerable attention from synthetic chemists, who have devoted substantial effort toward developing efficient and diverse methods for constructing this important motif. Many of the synthesized <em>cis</em>‐hydrindane compounds have been used as key intermediates or building blocks in the total synthesis of complex natural products. This review provides an overview of strategic approaches for synthesizing functionalized <em>cis</em>‐hydrindanes and its derivatives from 2000 to the present day, focusing on their application in natural product synthesis. By examining the diverse methods and their impact on natural product synthesis, this review will underscore the enduring importance of the <em>cis</em>‐hydrindane framework in both synthetic organic chemistry and medicinal chemistry.</div></div>","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"28 16","pages":"Article e202500006"},"PeriodicalIF":2.5,"publicationDate":"2025-04-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143477917","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* 新型螺罗苯并恶嗪吲哚啉的水介导化学选择性合成及螺罗苯并恶嗪吲哚衍生物的扩展合成*

IF 2.5 3区化学

European Journal of Organic Chemistry Pub Date : 2025-04-23 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":"10.1002/ejoc.202401488","url":null,"abstract":"<div><div>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.</div></div>","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"28 16","pages":"Article e202401488"},"PeriodicalIF":2.5,"publicationDate":"2025-04-23","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

Regioselective Formal Hydroamidation of Alkynes: Synthesis of α‐Substituted Acrylamides 炔烃的区域选择性形式氢酰胺化：α-取代的丙烯酰胺的合成

IF 2.5 3区化学

European Journal of Organic Chemistry Pub Date : 2025-04-23 DOI: 10.1002/ejoc.202401484

Cheong Hoon Park , Seeun Lim , Prof. Dr. Byunghyuck Jung , Prof. Dr. Yunmi Lee

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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 CS<sub>2</sub> from <strong>Carbene</strong>–<strong>CS<sub>2</sub></strong> adducts formed by three distinct singlet carbenes: cyclic (alkyl)(amino)carbene (<strong>CAAC</strong>); N‐heterocyclic carbene (<strong>NHC</strong>); and N,N’‐diamidocarbene (<strong>DAC</strong>). Under ball‐milling conditions, these adducts exhibit notably different reactivities; <strong>DAC</strong>–<strong>CS<sub>2</sub></strong> releases CS<sub>2</sub> completely within 20 min, <strong>NHC</strong>–<strong>CS<sub>2</sub></strong> has a slower release rate, while <strong>CAAC</strong>–<strong>CS<sub>2</sub></strong> decomposes into a complex mixture. DFT calculations reveal that the release of CS<sub>2</sub> from <strong>CAAC</strong>–<strong>CS<sub>2</sub></strong> 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 <strong>CAAC</strong>, which correlates with a stronger bond with CS<sub>2</sub>, 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

引用次数: 0