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Visible‐Light‐Promoted Willgerodt–Kindler‐Type Thioamidation Reaction of Amines, α‐Ketoacids, and Elemental Sulfur 可见光促进了胺、α -酮酸和单质硫的Willgerodt-Kindler型硫胺化反应
IF 2.7 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-09-26 DOI: 10.1002/ejoc.202500708
Jigang Gao , Taimin Wang , Peng Li , Yun Luo , Lijing Fang , Hongbin Zhai , Jinlin Wang , Bin Cheng
{"title":"Visible‐Light‐Promoted Willgerodt–Kindler‐Type Thioamidation Reaction of Amines, α‐Ketoacids, and Elemental Sulfur","authors":"Jigang Gao ,&nbsp;Taimin Wang ,&nbsp;Peng Li ,&nbsp;Yun Luo ,&nbsp;Lijing Fang ,&nbsp;Hongbin Zhai ,&nbsp;Jinlin Wang ,&nbsp;Bin Cheng","doi":"10.1002/ejoc.202500708","DOIUrl":"10.1002/ejoc.202500708","url":null,"abstract":"<div><div>A visible‐light‐promoted Willgerodt–Kindler‐type thioamidation reaction of amines, <em>α</em>‐ketoacids, and elemental sulfur under mild conditions has been developed. A wide variety of readily available feedstocks are extensively investigated, including primary/secondary amines, aryl/alkyl amines, ammonium salts, amino‐containing pharmaceuticals, and amino acid esters, providing 27 examples of thioamides in moderate to high yields under metal‐free and oxidant‐free conditions.</div></div>","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"28 35","pages":"Article e202500708"},"PeriodicalIF":2.7,"publicationDate":"2025-09-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144715657","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
Escape from Flatland: Pericyclic Reactions and Rearrangements of Diazofluorene with Biarylcyclooctynes for the Generation of Helicene‐Like Phenanthro‐Pyrazoles 逃离平原：重氮芴与双芳基环琴的周环反应和重排生成类螺旋烯类菲唑
IF 2.7 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-09-26 DOI: 10.1002/ejoc.202500130
Atul Ojha , Eshani Das , Xinsong Lin , Brian Gold
{"title":"Escape from Flatland: Pericyclic Reactions and Rearrangements of Diazofluorene with Biarylcyclooctynes for the Generation of Helicene‐Like Phenanthro‐Pyrazoles","authors":"Atul Ojha ,&nbsp;Eshani Das ,&nbsp;Xinsong Lin ,&nbsp;Brian Gold","doi":"10.1002/ejoc.202500130","DOIUrl":"10.1002/ejoc.202500130","url":null,"abstract":"<div><div>Herein, the voyage of two flat, highly unsaturated systems into the third dimension is reported. Specifically, the 1,3‐dipolar cycloadditions of 9‐diazofluorene with a rapidly growing class of strained dipolarophile—biarylcyclooctynes—are investigated. It is found that the initial spirocyclic 3<em>H</em>‐pyrazole cycloadducts are isolable and can be subjected to controllable [1,5]‐sigmatropic shifts. These van Alphen–Hüttel rearrangements generate either the metastable 4<em>H</em>‐pyrazoles—another spirocyclic fused‐ring system with a highly contorted structure—or the thermodynamically favored 1<em>H</em>‐pyrazoles. The 1<em>H</em>‐pyrazoles display extended conjugation and can be classified as [5]‐helicenes containing a phenanthro‐pyrazole fused to a dihydro‐cyclooctatetraene. Overall, these studies provide a modular framework to control heteroatom placement, ring size, and ring fusion in the syntheses of carbon‐rich materials.</div></div>","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"28 35","pages":"Article e202500130"},"PeriodicalIF":2.7,"publicationDate":"2025-09-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143927150","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
Phosphorus Heterocycles for Electroluminescence 电致发光用磷杂环化合物
IF 2.7 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-09-26 DOI: 10.1002/ejoc.202500248
Weihao Li , Feifei Gao , Hui Xu
{"title":"Phosphorus Heterocycles for Electroluminescence","authors":"Weihao Li ,&nbsp;Feifei Gao ,&nbsp;Hui Xu","doi":"10.1002/ejoc.202500248","DOIUrl":"10.1002/ejoc.202500248","url":null,"abstract":"<div><div>Phosphorus‐containing heterocyclic compounds exhibit significant potential for applications in electroluminescence, owing to their distinctive electronic structures and varied chemical properties. Phosphorus heterocycles serve multifunctional roles within organic light‐emitting diodes (OLEDs), including as emitters, host matrices, and electron and hole blocking layers, contributing to enhanced device performance. Their intrinsic structural characteristics confer key advantages, including superior thermal stability, high fluorescence quantum yields, and suitable energy level alignment, all of which are essential for optimizing electroluminescent (EL) efficiency. Herein, the recent progress of EL phosphorus‐containing heterocyclics materials is overviewed and their structure–property relationships, which would provide insights into expanding the applicability of OLEDs is discussed.</div></div>","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"28 35","pages":"Article e202500248"},"PeriodicalIF":2.7,"publicationDate":"2025-09-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143880867","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
Fast Oxidative Coupling Giving Functionalized Biaryls via Organocuprates 通过有机羧酸酯快速氧化偶联得到功能化双芳基
IF 2.7 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-09-26 DOI: 10.1002/ejoc.202500072
Kazuhiro Okamoto , Ruka Ebisawa , Hiroki Nakayama , Aiichiro Nagaki
{"title":"Fast Oxidative Coupling Giving Functionalized Biaryls via Organocuprates","authors":"Kazuhiro Okamoto ,&nbsp;Ruka Ebisawa ,&nbsp;Hiroki Nakayama ,&nbsp;Aiichiro Nagaki","doi":"10.1002/ejoc.202500072","DOIUrl":"10.1002/ejoc.202500072","url":null,"abstract":"<div><div>A fast, continuous‐flow, and sequential reaction system composed of organolithium generation–transmetalation–coupling within seconds are developed. The choice of oxidants and the equivalent of copper species remarkably vary the reaction selectivity toward the biaryl coupling and/or the phenol formation. Short‐lived aryllithium species, including bromo‐, cyano‐, or nitro‐substituents, are successfully controlled under fast‐flow conditions, despite the instability after transmetalation giving the organocopper species.</div></div>","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"28 35","pages":"Article e202500072"},"PeriodicalIF":2.7,"publicationDate":"2025-09-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144786857","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
Asymmetric Synthesis through N‐Heterocyclic Carbene Catalysis: A Comprehensive Review of Catalyst Diversity and Applications N -杂环卡宾催化不对称合成：催化剂多样性及其应用综述
IF 2.7 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-09-26 DOI: 10.1002/ejoc.202500474
Jisna Jose , Mohd Aamir Mumtaz , Mohammad Fareed , Thomas V Mathew
{"title":"Asymmetric Synthesis through N‐Heterocyclic Carbene Catalysis: A Comprehensive Review of Catalyst Diversity and Applications","authors":"Jisna Jose ,&nbsp;Mohd Aamir Mumtaz ,&nbsp;Mohammad Fareed ,&nbsp;Thomas V Mathew","doi":"10.1002/ejoc.202500474","DOIUrl":"10.1002/ejoc.202500474","url":null,"abstract":"<div><div>N‐Heterocyclic carbenes (NHCs) have become prominent organocatalysts, facilitating a diverse array of transformations characterized by high levels of chemo‐, regio‐, and enantioselectivity. This review comprehensively examines the latest developments in NHC‐catalyzed asymmetric reactions, emphasizing their roles in synthesizing architecturally intricate and pharmacologically significant compounds. Recent advances in NHC scaffold design, particularly modifications at the N‐substituent and backbone, have significantly enhanced catalyst performance. This review highlights mechanistic insights and stereochemical outcomes that shed light on the selectivity and efficiency of these catalysts. This review aims to provide a comprehensive and updated perspective that addresses recent gaps in the literature and highlights the expanding role of NHCs in sustainable and stereoselective chemical synthesis.</div></div>","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"28 35","pages":"Article e202500474"},"PeriodicalIF":2.7,"publicationDate":"2025-09-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144770023","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
Employing Multicomponent Reactions in Heterocycle Synthesis: Recent Advances 多组分反应在杂环合成中的应用研究进展
IF 2.7 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-09-26 DOI: 10.1002/ejoc.202500337
Tapas Ghosh , Sk Shamim Ahamed , Rahul Paul , Paramita Saha
{"title":"Employing Multicomponent Reactions in Heterocycle Synthesis: Recent Advances","authors":"Tapas Ghosh ,&nbsp;Sk Shamim Ahamed ,&nbsp;Rahul Paul ,&nbsp;Paramita Saha","doi":"10.1002/ejoc.202500337","DOIUrl":"10.1002/ejoc.202500337","url":null,"abstract":"<div><div>Multicomponent reactions (MCRs) have paved their way as highly reliable tool in contemporary chemistry, serving not only as an atom economic version but also as an efficient one‐pot protocol in the synthesis of various pharmaceutically relevant heterocycles. This review article seeks to present a comprehensive overview of the significant heterocyclic ring formations facilitated by multicomponent cascade reactions, namely Ugi, Biginelli, Passerini, and other reactions. This review also highlights recent advancements over the past decade in the application of classical and modern MCRs—such as the Ugi, Biginelli, Passerini, and domino‐type reactions—for the construction of nitrogen‐, oxygen‐, and sulfur‐containing heterocycles of pharmaceutical and materials relevance. Additionally, the biological relevance of the heterocycles is discussed, offering insights into the synthetic utility and functional importance of MCR‐derived frameworks. Besides, this review article is dedicated to deliver in depth mechanistic insights and authoritative presentation and critical comments on crucial reactions.</div></div>","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"28 35","pages":"Article e202500337"},"PeriodicalIF":2.7,"publicationDate":"2025-09-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144503703","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
Fluorescence and Chiroptical Properties of Cyclic Aromatic Triamides with Isolated and Extended Conjugated Systems 环芳香族三酰胺分离和扩展共轭体系的荧光和旋热性质
IF 2.7 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-09-26 DOI: 10.1002/ejoc.202500673
Koji Takagi , Taiga Shirai , Daiki Miyamoto , Takuya Nakashima , Tomoyuki Ikai , Yutaka Ie , Takanori Fukushima
{"title":"Fluorescence and Chiroptical Properties of Cyclic Aromatic Triamides with Isolated and Extended Conjugated Systems","authors":"Koji Takagi ,&nbsp;Taiga Shirai ,&nbsp;Daiki Miyamoto ,&nbsp;Takuya Nakashima ,&nbsp;Tomoyuki Ikai ,&nbsp;Yutaka Ie ,&nbsp;Takanori Fukushima","doi":"10.1002/ejoc.202500673","DOIUrl":"10.1002/ejoc.202500673","url":null,"abstract":"<div><div>This study synthesizes cyclic and acyclic aromatic triamides with conjugated systems to establish molecular design guidelines for obtaining reliable circularly polarized luminescence (CPL)‐active materials. For the compounds with the phenylacetylene unit, the acyclic derivative shows a single fluorescence at 381 nm, whereas the cyclic ones show dual fluorescence. The long‐wavelength emission at 545 nm is significant for the compound with three π‐conjugated systems measured at 25 °C. The fluorescence quantum yield and lifetime depend on the number of conjugated systems introduced into the cyclic structure. When the enantiomers of the cyclic compounds is isolated by chiral high‐performance liquid chromatography, all of them shows circular dichroism (CD) activity, but only the compound with the three conjugated systems shows CPL with the anisotropy factor <em>g</em><sub>lum</sub> = 4.0 × 10<sup>−3</sup>. On the other hand, this study also synthesizes two cyclic aromatic triamides with the naphthylacetylene unit and succeeded in optical resolutions. The fluorescence quantum yields (Φ = 0.80 and 0.34) are improved, and a single sky blue emission is observed. The CD and CPL anisotropy factors are larger than those of the phenyl counterpart, and the CPL shows a B<sub>CPL</sub> value of about 30 <span>M</span><sup>−1</sup> cm<sup>−1</sup>.</div></div>","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"28 35","pages":"Article e202500673"},"PeriodicalIF":2.7,"publicationDate":"2025-09-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144911123","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
Rhodium‐Catalyzed Directed C–H Heteroarylation of 2‐Pyridones Using Cyclic Iodonium Ylides 铑催化环碘酰化2-吡啶酮的定向C-H杂芳化反应
IF 2.7 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-09-26 DOI: 10.1002/ejoc.202500306
Zhan‐Wei Fu , Shi Cao , Mu‐Peng Luo , Shu‐Rong Ban , Shou‐Guo Wang
{"title":"Rhodium‐Catalyzed Directed C–H Heteroarylation of 2‐Pyridones Using Cyclic Iodonium Ylides","authors":"Zhan‐Wei Fu ,&nbsp;Shi Cao ,&nbsp;Mu‐Peng Luo ,&nbsp;Shu‐Rong Ban ,&nbsp;Shou‐Guo Wang","doi":"10.1002/ejoc.202500306","DOIUrl":"10.1002/ejoc.202500306","url":null,"abstract":"<div><div>2‐Pyridone is a crucial building block in bioactive natural products and serves as a vital intermediate for the synthesis of bioactive nitrogen‐containing heterocycles. Recent advancements in transition‐metal‐catalyzed C–H functionalization have enabled the direct modification of 2‐pyridones, circumventing the need for prefunctionalization. Herein, a Rh(III)‐catalyzed, C6‐selective C–H heteroarylation of 2‐pyridones using cyclic iodonium ylides as carbene precursors is reported. The versatility and broad applicability of this method are demonstrated through the efficient synthesis of diverse compounds featuring both 2‐pyridone‐pyridine and cyclic 1,3‐dicarbonyl derivatives.</div></div>","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"28 35","pages":"Article e202500306"},"PeriodicalIF":2.7,"publicationDate":"2025-09-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143940570","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 2‐Fluoropyrroles via [4 + 1] Cycloaddition of α,β‐Unsaturated Imines with In Situ‐Generated Difluorocarbene α，β -不饱和亚胺与原位生成的二氟苯[4 + 1]环加成合成2 -氟吡咯
IF 2.7 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-09-26 DOI: 10.1002/ejoc.202500586
Kohei Fuchibe , Takaya Miura , Junji Ichikawa
{"title":"Synthesis of 2‐Fluoropyrroles via [4 + 1] Cycloaddition of α,β‐Unsaturated Imines with In Situ‐Generated Difluorocarbene","authors":"Kohei Fuchibe ,&nbsp;Takaya Miura ,&nbsp;Junji Ichikawa","doi":"10.1002/ejoc.202500586","DOIUrl":"10.1002/ejoc.202500586","url":null,"abstract":"<div><div>2‐Fluoropyrroles are synthesized via the [4 + 1] cycloaddition of α,β‐unsaturated imines with difluorocarbene (:CF<sub>2</sub>), which is generated in situ from trimethylsilyl 2,2‐difluoro‐2‐(fluorosulfonyl)acetate (TFDA). The α,β‐unsaturated imines are treated with TFDA in the presence of a Proton Sponge catalyst, facilitating the catalytic generation of: CF<sub>2</sub>. The resulting carbene underwent [4 + 1] cycloaddition with imines through azomethine ylide intermediates, yielding 5,5‐difluoropyrrolines. Subsequent dehydrofluorination with 1,8‐diazabicyclo[5.4.0]‐7‐undecene produced the targeted 2‐fluoropyrroles.</div></div>","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"28 35","pages":"Article e202500586"},"PeriodicalIF":2.7,"publicationDate":"2025-09-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144715658","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‐Induced Singlet‐Oxygen‐Mediated Synthesis of Substituted Benzo[c]chromeno[4,3,2‐gh]phenanthridines† 可见光诱导单线态氧介导取代苯并[c]色[4,3,2 - gh]菲咯啉的合成
IF 2.7 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-09-26 DOI: 10.1002/ejoc.202500473
Mukesh Kumar , Sabina Yashmin , Diptajit Kumar Das , Kalishankar Bhattacharyya , Abu Taleb Khan
{"title":"Visible Light‐Induced Singlet‐Oxygen‐Mediated Synthesis of Substituted Benzo[c]chromeno[4,3,2‐gh]phenanthridines†","authors":"Mukesh Kumar ,&nbsp;Sabina Yashmin ,&nbsp;Diptajit Kumar Das ,&nbsp;Kalishankar Bhattacharyya ,&nbsp;Abu Taleb Khan","doi":"10.1002/ejoc.202500473","DOIUrl":"10.1002/ejoc.202500473","url":null,"abstract":"<div><div>Visible‐light‐promoted environmentally benign synthesis of various 9‐alkylbenzo[<em>c</em>]chromeno[4,3,2‐<em>gh</em>]phenanthridine derivatives in the presence of 5 mol % disodium salt of eosin Y (EY) as photocatalyst is reported from 2‐(7,8,9,10‐tetrahydrobenzo[<em>c</em>]phe‐nanthridin‐6‐yl) phenol derivatives, which were prepared through a three‐component reaction. In the present protocol, EY‐photosensitized singlet oxygen (<sup>1</sup>O<sub>2</sub>) promotes intramolecular cyclization through an oxidative hetero‐crosscoupling reaction, followed by aromatization to provide the final product in a single step, which has not been reported earlier. The mechanism of the reaction was established through density functional theory calculation and by trapping of the oxygen radical intermediate <strong>A</strong> with Butylated Hydroxytoluene (BHT), which was confirmed through <sup>1</sup>H, <sup>13</sup>C NMR spectra, and HRMS. This process forms the highly fused hexacyclic heteroaromatics without requiring any metal catalyst or dehydrogenating agent. This intramolecular photocyclization, through the triplet energy transfer process, is a fascinating example of the oxidative coupling reaction via distal sp<sup>3</sup>‐CH.</div></div>","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"28 35","pages":"Article e202500473"},"PeriodicalIF":2.7,"publicationDate":"2025-09-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144237108","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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