European Journal of Organic Chemistry最新文献_第10页

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

引用次数: 0

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}

引用次数: 0

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

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

引用次数: 0

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}

引用次数: 0

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

引用次数: 0

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

引用次数: 0