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Transition Metal-Promoted Direct C-S and C-Se Bond Formation from Csp3-H Bonds
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-04-03 DOI: 10.1002/ejoc.202500111
Daniel da Silveira Rampon, Douglas B. Paixão, Diego Seckler, Carla M. B. Gomes, Gul Badshah, Gabriel P. Bueno, Paulo H. Schneider, Ricardo S. Schwab
{"title":"Transition Metal-Promoted Direct C-S and C-Se Bond Formation from Csp3-H Bonds","authors":"Daniel da Silveira Rampon, Douglas B. Paixão, Diego Seckler, Carla M. B. Gomes, Gul Badshah, Gabriel P. Bueno, Paulo H. Schneider, Ricardo S. Schwab","doi":"10.1002/ejoc.202500111","DOIUrl":"https://doi.org/10.1002/ejoc.202500111","url":null,"abstract":"The transition metal-catalyzed direct C−S and C−Se bond formation from C−H bonds has emerged as an efficient synthetic strategy for constructing previously inaccessible organochalcogen compounds, opening a new gateway to late-stage functionalization of pharmaceutical-relevant molecules and organic functional materials. C−Y bonds (Y = S, Se, Te) also show outstanding strategic relevance as handles to access other valuable functional groups downstream in a synthetic route. Despite the significant progress, the chemo-, site-, and enantioselective C−S and C−Se bond formation from unactivated Csp3−H bonds is still challenging owing to its low polarity and inertness. Here, we provide a comprehensive overview of the transition-metal-catalyzed direct conversion of unactivated Csp3−H to C−S and C−Se bonds in the last decade, looking to motivate the continuous discovery of innovative and efficient systems for these transformations.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"107 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-04-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143767149","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
Gold(I)-Catalyzed Allylation and Tandem Allylation–Cycloisomerization of Stannylated Propargyl Acetates with Allylsilanes
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-04-03 DOI: 10.1002/ejoc.202500253
Yoshikazu Horino, Nene Murata, Sota Akima, Syed R. Hussaini
{"title":"Gold(I)-Catalyzed Allylation and Tandem Allylation–Cycloisomerization of Stannylated Propargyl Acetates with Allylsilanes","authors":"Yoshikazu Horino, Nene Murata, Sota Akima, Syed R. Hussaini","doi":"10.1002/ejoc.202500253","DOIUrl":"https://doi.org/10.1002/ejoc.202500253","url":null,"abstract":"Bicyclo[3.1.0]hex-2-enes, synthesized by the cycloisomerization of 1,5-enynes, serve as key scaffolds in various natural products. Gold(I)-catalyzed cycloisomerization of 1,5-enynes is an efficient route to bicyclo[3.1.0]hex-2-enes. However, gold(I)-catalyzed 1,5-enyne synthesis, particularly with a terminal alkyne, has not yet been fully explored. This study presents a mild and general method for the gold(I)-catalyzed allylation and tandem allylation–cycloisomerization of stannylated propargyl acetates with allylsilanes, yielding 1,5-enynes with terminal alkyne moiety and bicyclo[3.1.0]hex-2-enes. The catalytic system ((4-MeOC6H4)3PAuCl/AgSbF6) enabled the efficient synthesis of 1,5-enynes with good to high yields and regioselectivities. In addition, gold(I)-catalyzed tandem allylation–cycloisomerization using (JohnPhos)Au(MeCN)SbF6 afforded bicyclo[3.1.0]hex-2-enes with high regiocontrol. Stannylated propargyl acetates proved crucial in enhancing selectivity for both product classes.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"6 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-04-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143767160","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 in Transition Metal-Free Strategies for the Transformation of Amides into Carbonyl Compounds
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-04-03 DOI: 10.1002/ejoc.202500210
Karthik Rajan Rajamanickam, Robin Prakash Sirvin Rajan, Nithin Pootheri, Chin-Fa Lee, Sunwoo Lee
{"title":"Recent Advances in Transition Metal-Free Strategies for the Transformation of Amides into Carbonyl Compounds","authors":"Karthik Rajan Rajamanickam, Robin Prakash Sirvin Rajan, Nithin Pootheri, Chin-Fa Lee, Sunwoo Lee","doi":"10.1002/ejoc.202500210","DOIUrl":"https://doi.org/10.1002/ejoc.202500210","url":null,"abstract":"Amides are fundamental functional groups in organic synthesis and play crucial roles in medicinal chemistry and material science. Traditionally, amide transformations have often relied on transition-metal catalysts; however, recent advances have demonstrated efficient transition-metal-free strategies for amide bond activation. This review provides a comprehensive overview of emerging methodologies that enable selective formation of C–N, C–C, C–O, C–H, and C–X bonds. Key developments that offer sustainable and practical alternatives to conventional approaches include borate- and boronic acid-mediated transamidations, phosphoric acid-promoted transformations, and radical-based strategies. Additionally, nucleophilic substitutions with carbon, oxygen, and nitrogen-based nucleophiles have expanded the synthetic utility of amides by yielding diverse carbonyl and heterocyclic compounds. Mechanistic insights into these transformations reveal the role of electronic and steric effects in amide reactivity. By categorizing these methodologies based on amide substrates and reaction pathways, this review aims to provide a valuable resource for researchers seeking efficient, metal-free strategies for amide bond manipulation.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"20 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-04-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143767162","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
Diazo compounds under visible light: Stereoselective synthesis of cyclic architectures
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-04-03 DOI: 10.1002/ejoc.202500329
Suven Das, Arpita Dutta
{"title":"Diazo compounds under visible light: Stereoselective synthesis of cyclic architectures","authors":"Suven Das, Arpita Dutta","doi":"10.1002/ejoc.202500329","DOIUrl":"https://doi.org/10.1002/ejoc.202500329","url":null,"abstract":"Diazo compounds are versatile and valuable reagents in organic synthesis. The reaction of diazo substrates under photochemical conditions find high selectivity compared to that under thermal conditions. In the presence of light, they can act as carbene precursors or radical sources depending upon the reaction conditions and catalysts used. Recent years have witnessed a great advancement in visible-light-induced photochemistry of diazo compounds for asymmetric access to various cyclic compounds. In this review, we summarized recent advances (2020-2024) in stereoselective synthesis of cyclic scaffolds via visible-light irradiation of diazo compounds. This review is organized according to the ring size of the synthesized compounds, viz., three, four, five, six, seven and higher membered ring systems. With an emphasis of mechanistic insights and scope of the reactions, this review shades light on current trends in this emerging field.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"26 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-04-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143767144","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
Chemo- and Regio-selective Dual-Functionalization of Arenes: Synthesis of Multi-Functional Aromatics via Aromaticity Destruction-Reconstruction Process
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-04-03 DOI: 10.1002/ejoc.202500085
Saddam Husen, Ravindra Kumar
{"title":"Chemo- and Regio-selective Dual-Functionalization of Arenes: Synthesis of Multi-Functional Aromatics via Aromaticity Destruction-Reconstruction Process","authors":"Saddam Husen, Ravindra Kumar","doi":"10.1002/ejoc.202500085","DOIUrl":"https://doi.org/10.1002/ejoc.202500085","url":null,"abstract":"Dual functionalization of arenes via a dearomatization-functionalization-rearomatization strategy facilitates chemo- and regioselective functionalization on phenols or anilines. This strategy proceeds via 2,5-cyclohexadienones and 2,5-cyclohexadienimines intermediates and permits a wide range of functionalizations with various coupling partners, enabling rapid molecular diversification under sustainable and transition metal-free conditions.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"3 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-04-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143767145","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: Unraveling Phenanthrenoid Dimerization in Juncus acutus: A DFT-Guided Exploration of Radical-Coupling Reaction Mechanisms (Eur. J. Org. Chem. 13/2025)
IF 2.5 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-04-03 DOI: 10.1002/ejoc.202581301
Dr. Federico Coppola, Prof. Paola Cimino, Prof. Nadia Rega, Dr. Simona Zuppolini, Prof. Giovanni Di Fabio, Prof. Armando Zarrelli
{"title":"Front Cover: Unraveling Phenanthrenoid Dimerization in Juncus acutus: A DFT-Guided Exploration of Radical-Coupling Reaction Mechanisms (Eur. J. Org. Chem. 13/2025)","authors":"Dr. Federico Coppola,&nbsp;Prof. Paola Cimino,&nbsp;Prof. Nadia Rega,&nbsp;Dr. Simona Zuppolini,&nbsp;Prof. Giovanni Di Fabio,&nbsp;Prof. Armando Zarrelli","doi":"10.1002/ejoc.202581301","DOIUrl":"https://doi.org/10.1002/ejoc.202581301","url":null,"abstract":"<p><b>The Front Cover</b> illustrates the radical-driven dimerization of phenanthrenoid compounds in <i>Juncus acutus</i>. Density functional theory calculations reveal how OH radicals initiate regioselective coupling, leading to homodimer and heterodimer formation. The reaction follows a two-state reactivity mechanism, involving a triplet π–π stacked intermediate and a water-mediated keto–enol tautomerization. More information can be found in the Research Article by F. Coppola, A. Zarrelli and co-workers (DOI: 10.1002/ejoc.202401123).\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 13","pages":""},"PeriodicalIF":2.5,"publicationDate":"2025-04-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/ejoc.202581301","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143770164","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
Heteroatom‐functionalized λ5‐Phosphinines – Synthesis and Properties
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-04-02 DOI: 10.1002/ejoc.202500256
Minoru Hayashi, Makoto Yano, Dam Thi Huyen Trang, Ryusei Ikeda, Hidetoshi Ohta
{"title":"Heteroatom‐functionalized λ5‐Phosphinines – Synthesis and Properties","authors":"Minoru Hayashi, Makoto Yano, Dam Thi Huyen Trang, Ryusei Ikeda, Hidetoshi Ohta","doi":"10.1002/ejoc.202500256","DOIUrl":"https://doi.org/10.1002/ejoc.202500256","url":null,"abstract":"λ5‐Phosphinines with a heteroatom functionality at the C‐4 position were synthesized by several newly developed procedures. S‐, P‐, N‐, and B‐substituted phosphinines exhibit highly effective emission with variable and tunable wavelength according to the substituent electronic density. Photophysical properties with demonstrative examples of qualitative fluorescent detection were also reported.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"33 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-04-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143757769","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
Multianalytical Characterization of Acrylic Industrial Paints Used in Contemporary Mural Art
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-04-01 DOI: 10.1002/ejoc.202400759
Andrea Poliszuk, Laura Gelabert, Gabriel O. Ybarra, Marta S. Maier
{"title":"Multianalytical Characterization of Acrylic Industrial Paints Used in Contemporary Mural Art","authors":"Andrea Poliszuk, Laura Gelabert, Gabriel O. Ybarra, Marta S. Maier","doi":"10.1002/ejoc.202400759","DOIUrl":"https://doi.org/10.1002/ejoc.202400759","url":null,"abstract":"Contemporary outdoor mural paintings are artworks affected by exposure to sunlight, rain, and environmental pollutants. Three commercial white paints used by street artists are characterized by a multianalytical approach. Analysis of cross sections from samples of two mural paintings reveals the painting technique, while characterization of their materials explains differences in their conservation conditions.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"58 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-04-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143745460","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
Hydrosilylation of Terminal Alkenes Catalyzed by a Scandium Metalloligand Supported Ni(0) Complex
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-04-01 DOI: 10.1002/ejoc.202500069
Lei Ma, Dongjing Hong, Peng Cui
{"title":"Hydrosilylation of Terminal Alkenes Catalyzed by a Scandium Metalloligand Supported Ni(0) Complex","authors":"Lei Ma, Dongjing Hong, Peng Cui","doi":"10.1002/ejoc.202500069","DOIUrl":"https://doi.org/10.1002/ejoc.202500069","url":null,"abstract":"Hydrosilylation of terminal alkenes catalyzed by a scandium metalloligand supported Ni(0) complex were studied. The anti‐Markovnikov products were obtained in 62~89% yield, along with the alkanes and 1,1,2,2‐tetraphenyldisilane as minor products. The resting‐state complexes of hydrosilylation reactions were isolated and characterized by spectroscopic method and X‐ray diffraction studies, which represent rare‐example of Ni(0) silyl complexes supported by scandium ions via a Ni(0)→Sc(III) interaction. The catalytic cycle was proposed to be redox neutral with Ni(0) center, and was facilitated by metal‐ligand cooperation involving the Ni(0)‐Si bond.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"72 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-04-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143745091","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
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