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Synthesis of Quinolino[4,3‐j]phenanthridines and their Photophysical Characterization 喹啉并[4,3-j]菲啶的合成及其光物理表征
IF 2.5 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-04-01 DOI: 10.1002/ejoc.202401416
M. Sc. Felix R. Schumann , Prof. Dr. Joachim Podlech
{"title":"Synthesis of Quinolino[4,3‐j]phenanthridines and their Photophysical Characterization","authors":"M. Sc. Felix R. Schumann ,&nbsp;Prof. Dr. Joachim Podlech","doi":"10.1002/ejoc.202401416","DOIUrl":"10.1002/ejoc.202401416","url":null,"abstract":"<div><div>Quinolino[4,3‐<em>j</em>]phenanthridines were synthesized from <em>para</em>‐terphenyl‐2,2′′‐diamines, which were obtained by cross‐coupling reactions. The diamines were converted into amides and <em>ortho</em>‐cyclized to quinolino[4,3‐<em>j</em>]phenanthridines using <em>Morgan‐Walls</em> reactions. Prolonged reaction times were required in these electrophilic substitution reactions to overcome the respective deactivated intermediates formed after the first <em>ortho</em> fusion. Optophysical properties were determined by UV/Vis and fluorescence spectroscopy and calculated by quantum chemical calculations. The compounds exhibit rather small HOMO/LUMO gaps and a remarkable bathochromic shift of luminescence upon protonation, what makes these compounds promising candidates for optoelectronic applications.</div></div>","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"28 13","pages":"Article e202401416"},"PeriodicalIF":2.5,"publicationDate":"2025-04-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/ejoc.202401416","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143418432","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
Successors of SmI2: Next Generation Metal, Photo and Electro‐Catalysis for Reductive Organic Synthesis SmI2 的继承者：用于还原性有机合成的新一代金属、光催化和电催化技术
IF 2.5 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-04-01 DOI: 10.1002/ejoc.202401342
Sonalin Senapati , Subhendu Jena , Manwar Box , Sandeepan Maity
{"title":"Successors of SmI2: Next Generation Metal, Photo and Electro‐Catalysis for Reductive Organic Synthesis","authors":"Sonalin Senapati ,&nbsp;Subhendu Jena ,&nbsp;Manwar Box ,&nbsp;Sandeepan Maity","doi":"10.1002/ejoc.202401342","DOIUrl":"10.1002/ejoc.202401342","url":null,"abstract":"<div><div>Electron transfer plays a pivotal role in generating radical intermediates which are pillars of constructing complex molecular structure. Since the introduction by Kagan, SmI<sub>2</sub> played a key role in the single electron transfer mediated reductive transformations. Despite significant applications of SmI<sub>2</sub> in high profile synthesis of natural products, usage of SmI<sub>2</sub> was discoursed due to high molecular weight of reagent, less solubility and most importantly stoichiometric nature of the reactions. Recent years have witnessed a renaissance in photo‐and electro‐catalytic reactions which are more sustainable in nature. A handful of these reactions showed the potential to replace SmI<sub>2</sub> as more sustainable and greener alternative. This prospective article aims to demonstrate potential reducing systems to replace the use of SmI<sub>2</sub>.</div></div>","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"28 13","pages":"Article e202401342"},"PeriodicalIF":2.5,"publicationDate":"2025-04-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143640926","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
Samarium Diiodide/Samarium‐Mediated Deoxygenative Hydroborylation of Aldehydes 二碘化钐/钐介导的醛类脱氧氢硼化反应
IF 2.5 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-04-01 DOI: 10.1002/ejoc.202401249
Prof. Dr. Chengwei Liu , Yilin Ma , Wei Zhou
{"title":"Samarium Diiodide/Samarium‐Mediated Deoxygenative Hydroborylation of Aldehydes","authors":"Prof. Dr. Chengwei Liu ,&nbsp;Yilin Ma ,&nbsp;Wei Zhou","doi":"10.1002/ejoc.202401249","DOIUrl":"10.1002/ejoc.202401249","url":null,"abstract":"<div><div>A samarium diiodide/samarium‐mediated direct deoxygenative hydroborylation of aldehydes with hydroborate ester has been reported. In this method, unactivated aldehydes and hydroborate ester have been employed as starting materials for the synthesis of primary alkyl borate esters. Broad substrate scope and excellent functional group tolerance have demonstrated that this is a robust method for deoxygenative hydroborylation of aldehydes.</div></div>","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"28 13","pages":"Article e202401249"},"PeriodicalIF":2.5,"publicationDate":"2025-04-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142874619","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
2‐formyl‐5‐(hydroxymethyl)furan (HMF) derivatives as active complexing agent for CO2 insertion reaction
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-03-31 DOI: 10.1002/ejoc.202500119
Giulia Fiorani, Nicola Bragato, Mattia Annatelli, Alessandro Bernardi, Marco Bortoluzzi, Roberto Calmanti, Alvise Perosa, Maurizio Selva
{"title":"2‐formyl‐5‐(hydroxymethyl)furan (HMF) derivatives as active complexing agent for CO2 insertion reaction","authors":"Giulia Fiorani, Nicola Bragato, Mattia Annatelli, Alessandro Bernardi, Marco Bortoluzzi, Roberto Calmanti, Alvise Perosa, Maurizio Selva","doi":"10.1002/ejoc.202500119","DOIUrl":"https://doi.org/10.1002/ejoc.202500119","url":null,"abstract":"Renewable‐based furan compounds derived from 2‐formyl‐5‐(hydroxymethyl)furan (5‐HMF) were successfully employed as catalysts to synthesize cyclic organic carbonates through the reaction of carbon dioxide with epoxides. The effects of temperature, reaction time, reagent ratios, and carbon dioxide pressure were optimized before evaluating various bio‐based complexing agents in combination with different alkali metal halide salts. Among them, 2,5‐bis(hydroxymethyl)tetrahydrofuran (BHTHF) showed the highest efficiency as a complexing agent when paired with sodium bromide (NaBr), enabling the production of industrially relevant cyclic carbonates in high yields (12 examples, achieving 94‐99% epoxide conversion and 70‐99% carbonate selectivity) under mild pressure conditions (carbon dioxide pressure of 1‐10 bar, reaction time of 6 hours, and temperature of 120 °C). Additionally, the BHTHF/NaBr catalytic system demonstrated high stability, maintaining its performance over nine consecutive epoxide additions (8 mmol each) without any loss of efficiency.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"15 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-03-31","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143736671","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 of N,N'‐Bisindoles via Gold‐Catalyzed Formal (4+1) Cycloaddition
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-03-31 DOI: 10.1002/ejoc.202500193
Hao-Hui Zhang, Can Yang, Hao-Cheng Tian, Kuiyong Dong, Feng Shi
{"title":"Synthesis of N,N'‐Bisindoles via Gold‐Catalyzed Formal (4+1) Cycloaddition","authors":"Hao-Hui Zhang, Can Yang, Hao-Cheng Tian, Kuiyong Dong, Feng Shi","doi":"10.1002/ejoc.202500193","DOIUrl":"https://doi.org/10.1002/ejoc.202500193","url":null,"abstract":"Indole‐based heterocycles are commonly found in natural products and pharmaceuticals, so the synthesis of such heterocycles has become an important research area. In spite of the rapid development of this research area, the synthesis of N,N'‐bisindoles remains challenging and is far less developed. Herein, we present the synthesis of N,N'‐bisindoles via gold‐catalyzed formal (4+1) cycloaddition of alkynylcyclohexadienones with N‐aminoindoles, which involves a domino aza‐Meyer‐Schuster rearrangement/aza‐Michael addition sequence. This reaction allows for the formation of two C‐N bonds and the direct construction of indole ring, leading to the synthesis of a range of N,N'‐bisindoles in moderate to high yields with broad functional group tolerance. This work not only provides a new and efficient strategy toward the synthesis of N,N'‐bisindoles, but also enriches the research contents of formal (4+1) cycloadditions and domino reactions.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"58 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-03-31","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143736656","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
Total Synthesis of Pegaharmine I Enabled by Visible‐Light Photocatalytic Nitrone Formation
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-03-29 DOI: 10.1002/ejoc.202500245
Manikanta Swami Pothana, Huang-Chieh Lu, Bor-Cherng Hong, Su-Ying Chien
{"title":"Total Synthesis of Pegaharmine I Enabled by Visible‐Light Photocatalytic Nitrone Formation","authors":"Manikanta Swami Pothana, Huang-Chieh Lu, Bor-Cherng Hong, Su-Ying Chien","doi":"10.1002/ejoc.202500245","DOIUrl":"https://doi.org/10.1002/ejoc.202500245","url":null,"abstract":"The first total synthesis of pegaharmine I was accomplished by a three‐step strategy featuring a visible‐light‐photocatalyzed nitrone formation reaction as the key step. The structure of this natural product was confirmed by crystallographic analysis. Water‐promoted photocatalysis, achieved by incorporating water into the reaction medium, has also been established.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"102 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-03-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143736530","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
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
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