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Terpenes and Terpenoids: How Can we Use them?
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-03-28 DOI: 10.1002/ejoc.202401151
Jay Hanssens, Diego Meneses, Jordy M. Saya, Romano Orru
{"title":"Terpenes and Terpenoids: How Can we Use them?","authors":"Jay Hanssens, Diego Meneses, Jordy M. Saya, Romano Orru","doi":"10.1002/ejoc.202401151","DOIUrl":"https://doi.org/10.1002/ejoc.202401151","url":null,"abstract":"The employed feedstocks in chemical processes received substantial attention over the past decades, mainly due to the popularity of Werpy’s list of top‐value added chemicals from biomass reported in 2004. The conventional fossil‐based feedstocks are both depleting and can be damaging to the environment. This led to a surge to replace petroleum‐based chemicals to more renewable, bio‐based platform chemicals. Terpenes and terpenoids are a group of bio‐based compounds that are well known. However, there comprehensive overviews of the chemistry that these compounds have been used for are scarce. Herein, we provide a full comprehensive overview of the reported chemistry with terpenes while specifically highlighting their reactivity. Fifteen of the most common and useful monoterpenes and terpenoids are discussed, followed by a list of the remaining known compounds belonging to this group. The fifteen compounds have been employed in a vast number of chemical transformations with different applications including: polymerizations, total syntheses, chiral reagents/auxiliaries, pharmaceuticals, and chemical conversion to other useful bio‐based chemicals. We believe that the presented chemistry in this work will provide chemists with a useful tool that should facilitate and stimulate the search for more sustainable, renewable and environmentally friendly starting points for novel synthesis routes.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"183 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-03-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143723312","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: Selective Synthesis of Cyclic Dithiocarbonates Using Bis-Benzimidazolate Salts as Multifunctional Catalysts (Eur. J. Org. Chem. 12/2025)
IF 2.5 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-03-27 DOI: 10.1002/ejoc.202581201
Stephany Larissa da Silva Ribeiro, Cecília Maria Alves de Oliveira, Thaís Vieira Pereira da Silva, Olga Soares do Rêgo Barros, Meiry Edivirges Alvarenga, Felipe Terra Martins, Jorge Luiz Sônego Milani, Rafael Pavão das Chagas
{"title":"Front Cover: Selective Synthesis of Cyclic Dithiocarbonates Using Bis-Benzimidazolate Salts as Multifunctional Catalysts (Eur. J. Org. Chem. 12/2025)","authors":"Stephany Larissa da Silva Ribeiro,&nbsp;Cecília Maria Alves de Oliveira,&nbsp;Thaís Vieira Pereira da Silva,&nbsp;Olga Soares do Rêgo Barros,&nbsp;Meiry Edivirges Alvarenga,&nbsp;Felipe Terra Martins,&nbsp;Jorge Luiz Sônego Milani,&nbsp;Rafael Pavão das Chagas","doi":"10.1002/ejoc.202581201","DOIUrl":"https://doi.org/10.1002/ejoc.202581201","url":null,"abstract":"<p><b>The Front Cover</b> illustrates a multifunctional catalyst, symbolized by an octopus, orchestrating the reaction between carbon disulfide (CS₂) and an epoxide to form cyclic dithiocarbonate. The octopus's multiple arms represent the catalyst's multiple catalytic sites and modes of activation, enabling it to bind and activate both reactants, guiding them towards the final product. The Research Article by J. L. Sônego Milani, R. P. das Chagas and co-workers (DOI: 10.1002/ejoc.202401385) thus highlights an efficient and selective catalytic strategy for dithiocarbonate synthesis.\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 12","pages":""},"PeriodicalIF":2.5,"publicationDate":"2025-03-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/ejoc.202581201","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143707625","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
Synthesis of C2‐Silylated Indoles and Indolines Enabled by Iridium‐catalyzed Silylation of Indolines with Hydrosilanes
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-03-25 DOI: 10.1002/ejoc.202500166
Lei Wang, Xinni Tang, Hui Sun, Wenjie Hu, Li-Wen Xu, Lei Yang
{"title":"Synthesis of C2‐Silylated Indoles and Indolines Enabled by Iridium‐catalyzed Silylation of Indolines with Hydrosilanes","authors":"Lei Wang, Xinni Tang, Hui Sun, Wenjie Hu, Li-Wen Xu, Lei Yang","doi":"10.1002/ejoc.202500166","DOIUrl":"https://doi.org/10.1002/ejoc.202500166","url":null,"abstract":"We report an efficient iridium‐catalyzed one‐pot protocol for the synthesis of C2‐silylated indoles from indolines and hydrosilanes. Mechanistic investigations suggest that the transformation proceeds through a tandem dehydrogenation/C−H silylation pathway. Furthermore, an example of iridium‐catalyzed direct C2‐selective C(sp3)−H silylation of indolines is also disclosed.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"21 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-03-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143695864","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
Pd-Catalyzed Vicinal Difunctionalization of Carboranes with Benzoxazoles, Indoles and Anilines
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-03-25 DOI: 10.1002/ejoc.202500224
xin mu, Mengjie Zhu, Jiale Yu, Ruinian Jiang, Zikang Zhou
{"title":"Pd-Catalyzed Vicinal Difunctionalization of Carboranes with Benzoxazoles, Indoles and Anilines","authors":"xin mu, Mengjie Zhu, Jiale Yu, Ruinian Jiang, Zikang Zhou","doi":"10.1002/ejoc.202500224","DOIUrl":"https://doi.org/10.1002/ejoc.202500224","url":null,"abstract":"Icosahedral Carboranes have a wide range of applications in medicinal chemistry, material science, and catalysis. Although various methods have been disclosed for functionalizing carborane structures, the methods to incorporate different types of heterocycles are still lacking. This limitation is likely due to the functional group incompatibility under previously reported reaction conditions, and the sterically hindered environment on boron cluster vertices further complicated the reaction development. In this article, we present a streamlined protocol to prepare a new class of vicinal difunctionalized carboranes containing benzoxazoles, NH heterocycles and anilines. This method involves a direct cross-coupling between 9-bromo-m-carborane and benzoxazoles, thereby eliminating the necessity for preceding deprotonation of the acidic C2 proton present in benzoxazole. Subsequent regioselective iodination at the B(10) vertex of the carborane and the second cross-coupling reactions with diverse indoles and anilines resulted in the formation of the desired vicinal difunctionalized products.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"183 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-03-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143695907","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
Rh(III)-Catalyzed Cascade [3+3] Spiroannulation of N-Acyl Ketimines with Iodonium Ylides: Access to Spiro-N,O-Ketals
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-03-25 DOI: 10.1002/ejoc.202500155
Jiaojiao Wen, Xia Zhang, Chao Pi, Yangjie Wu, Xiuling Cui
{"title":"Rh(III)-Catalyzed Cascade [3+3] Spiroannulation of N-Acyl Ketimines with Iodonium Ylides: Access to Spiro-N,O-Ketals","authors":"Jiaojiao Wen, Xia Zhang, Chao Pi, Yangjie Wu, Xiuling Cui","doi":"10.1002/ejoc.202500155","DOIUrl":"https://doi.org/10.1002/ejoc.202500155","url":null,"abstract":"A Rh(III)-catalyzed cascade C-H activation/[3+3]spiroannulation of 3-hydroxy-3-arylisoindolin-1-ones with iodonium ylides has been developed. The method facilitates the efficient and selective construction of spirocyclic compounds in a one-pot manner, offering high yields and excellent conversion. The reaction proceeds via a highly regioselective process, resulting in the formation of spiro-N,O-ketals with remarkable chemo- and stereoselectivity. This strategy provides a valuable protocol for the synthesis of complex spirocyclics with potential applications in medicinal chemistry and materials science.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"16 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-03-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143695854","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
Amphiphilic Fluoro-Functionalized Cellulosic Materials: Synthesis, Characterization and Organic Dye Adsorption Properties
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-03-25 DOI: 10.1002/ejoc.202500035
Davide Ricci, Andrea Maio, Christian Jahns, Elena Piacenza, Delia Francesca Chillura Martino, Roberto Scaffaro, Margit Schulze, Andrea Pace, Carla Rizzo, Ivana Pibiri
{"title":"Amphiphilic Fluoro-Functionalized Cellulosic Materials: Synthesis, Characterization and Organic Dye Adsorption Properties","authors":"Davide Ricci, Andrea Maio, Christian Jahns, Elena Piacenza, Delia Francesca Chillura Martino, Roberto Scaffaro, Margit Schulze, Andrea Pace, Carla Rizzo, Ivana Pibiri","doi":"10.1002/ejoc.202500035","DOIUrl":"https://doi.org/10.1002/ejoc.202500035","url":null,"abstract":"The growing interest towards biopolymers application in amphiphilic conditions prompted us to explore the preparation of fluorinated cellulosic materials. Cellulose (CE) and carboxymethylcellulose (CMC) were functionalized with highly fluorinated pendants, through a nucleophilic aromatic substitution on 3-pentadecafluoroheptyl-5-pentafluorophenyl-1,2,4-oxadiazole (FOX). leading to the corresponding fluorinated biopolymers CE-FOX and CMC-FOX. Structural and thermal stability confirmed covalent attachment of the fluorinated moiety onto the cellulosic skeleton and highlighted an interesting two-dimensional texture of the CMC-FOX material. Hybrid and amphiphilic features of CE-FOX and CMC-FOX, were confirmed by water and oil contact angle measurements (WCA/OCA). Applications as adsorbent material for organic contaminants from an aqueous solution was tested by previously incorporating the functional biopolymer into sodium alginate (SA) hydrogel beads. Rhodamine B (RhB) was used as a model wastewater pollutant. Fluoro-functionalization led to a three- to eightfold increase in the dye-removal efficiency of the SA-incorporated biopolymer with respect to the corresponding non-fluorinated material (from 11% to 48% for SA/CE vs SA/CE-FOX beads and from 11% to 94% for SA/CMC vs SA/CMC-FOX beads). Recyclability tests showed good residual performance of SA/CMC-FOX beads after seven desorption/reuse cycles opening the way to more sustainable adsorbing processes for the removal of emerging pollutants from contaminated water.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"33 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-03-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143695908","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
Visible-Light-Driven E-selective Semihydrogenation and Its Application in the Treatment of Glioblastoma Multiforme
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-03-25 DOI: 10.1002/ejoc.202401370
Jinfei Yang, Huihui Yang, Xianglong Wang, Siqi Chen, Shutang Li, Baohu Li, Yanrui Fan, Haoze He, Zhou Lin
{"title":"Visible-Light-Driven E-selective Semihydrogenation and Its Application in the Treatment of Glioblastoma Multiforme","authors":"Jinfei Yang, Huihui Yang, Xianglong Wang, Siqi Chen, Shutang Li, Baohu Li, Yanrui Fan, Haoze He, Zhou Lin","doi":"10.1002/ejoc.202401370","DOIUrl":"https://doi.org/10.1002/ejoc.202401370","url":null,"abstract":"A visible-light-driven E-selective semihydrogenation scheme of alkyne compounds was developed for designing and synthesizing glioblastoma multiforme (GBM) inhibitors. In the present study, room-temperature semihydrogenation reactions of various alkyne compounds were successfully achieved under the irradiation of white light. The representative reaction mechanism was decoded through theoretical calculations and deuteration experiments, revealing the critical roles played by [Ir(Cp-Me5)Cl2]2, PdCl2, DPPE and TEOA as photosensitizer, catalyst, ligand, and electron donor, respectively. Our method exhibits excellent E-selectivity and broad functional group compatibility, and demonstrates its practical value by producing pinosylvin and its derivatives with strong inhibitory effects on U87 cells.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"35 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-03-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143703589","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 and reactivity of 1,4-ethano-1,5-naphthyridine derivatives using microwave activation or flow chemistry
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-03-25 DOI: 10.1002/ejoc.202401443
Mazarine Laurent, Rodolphe Vatinel, Stéphane Bostyn, Sylvain Routier, Frederic Buron
{"title":"Synthesis and reactivity of 1,4-ethano-1,5-naphthyridine derivatives using microwave activation or flow chemistry","authors":"Mazarine Laurent, Rodolphe Vatinel, Stéphane Bostyn, Sylvain Routier, Frederic Buron","doi":"10.1002/ejoc.202401443","DOIUrl":"https://doi.org/10.1002/ejoc.202401443","url":null,"abstract":"The design of some novel disubstituted 3,4-dihydro-2H-1,4-ethano-1,5-naphthyridine derivatives is reported under classical and flow methodologies. The series were developed from quinuclidinone, which afforded versatile platforms bearing one lactam function in position C-2 that was then used to create C–N bond using the Chan-Lam coupling reaction or in situ C–O bond activation via palladium-catalyzed cross-coupling reactions. The conditions were optimized, and a wide range of boronic acids were used to determine the scope and limitations of each method. To complete this study, a flow Suzuki-Miyaura process was established to afford polyfunctionalized 1,4-ethano-1,5-naphthyridine derivatives in high yields with a very efficient process (10 min.).","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"10 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-03-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143695852","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
Harnessing Electricity in Dehydrogenative Coupling: Transition Metal-Free Synthesis of Quinoline Derivatives
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-03-25 DOI: 10.1002/ejoc.202500316
Raju Dey, Vageesh M, Abhijeet Anand, Subir Panja
{"title":"Harnessing Electricity in Dehydrogenative Coupling: Transition Metal-Free Synthesis of Quinoline Derivatives","authors":"Raju Dey, Vageesh M, Abhijeet Anand, Subir Panja","doi":"10.1002/ejoc.202500316","DOIUrl":"https://doi.org/10.1002/ejoc.202500316","url":null,"abstract":"An efficient strategy is demonstrated for the electrocatalyitc synthesis of 2-aryl quinoline derivatives via an anodic dehydrogenation of 2-aminobenzyl alcohol molecules followed by condensation with carbonyl compounds at room temperature. The current protocol requires only electricity as the green oxidant, provides the desired products in good to excellent yield and is compatible with a wide range of functional groups.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"21 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-03-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143695853","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
Halogen‐Mediated Electrochemical C−N Bond Construction of Amine
IF 2.5 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-03-24 DOI: 10.1002/ejoc.202401352
Yu‐Yang Xie , Zhang Zhang , Ying‐Chun Wang
{"title":"Halogen‐Mediated Electrochemical C−N Bond Construction of Amine","authors":"Yu‐Yang Xie ,&nbsp;Zhang Zhang ,&nbsp;Ying‐Chun Wang","doi":"10.1002/ejoc.202401352","DOIUrl":"10.1002/ejoc.202401352","url":null,"abstract":"<div><div>Organic electrochemical synthesis stands out for its environmentally friendly and efficient characteristics. Among these approaches, halogen‐mediated indirect electrosynthesis has gained significant attention as an efficient strategy for C−N bond formation, widely applied in the synthesis of nitrogen‐containing compounds. This review highlights recent advances in direct C−N bond formation processes for various amines under halogen‐mediated electrosynthetic conditions. The features, scope, limitations, and proposed mechanisms of these transformations are discussed in detail. We aim to provide insights into expanding the applicability of halogen‐mediated electrosynthesis, contributing to the development of sustainable synthetic methodologies.</div></div>","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"28 12","pages":"Article e202401352"},"PeriodicalIF":2.5,"publicationDate":"2025-03-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143055274","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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