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Copper-Catalyzed Hydroxylation of Simple Fluoroaryl and Aryl Chlorides: A Route to (Fluoro)phenols 铜催化的简单氟芳基和芳基氯化物羟基化反应：生成（氟）酚的途径
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2026-10-13 Epub Date: 2026-08-26 DOI: 10.1002/ejoc.70806
Vikas Kumar Singh, Kailaskumar Borate, Roland Goetz, Rahul Kaduskar, Souvik Rakshit, Harish Shinde, Thomas Schaub, Christian Winter, A. Stephen K. Hashmi, Jean-Pierre B. Lindner
{"title":"Copper-Catalyzed Hydroxylation of Simple Fluoroaryl and Aryl Chlorides: A Route to (Fluoro)phenols","authors":"Vikas Kumar Singh,&nbsp;Kailaskumar Borate,&nbsp;Roland Goetz,&nbsp;Rahul Kaduskar,&nbsp;Souvik Rakshit,&nbsp;Harish Shinde,&nbsp;Thomas Schaub,&nbsp;Christian Winter,&nbsp;A. Stephen K. Hashmi,&nbsp;Jean-Pierre B. Lindner","doi":"10.1002/ejoc.70806","DOIUrl":"10.1002/ejoc.70806","url":null,"abstract":"<p>A copper-catalyzed conversion of polyfluoroaryl chlorides to the corresponding phenols was developed. A simple ligand system was applied, as well as potassium carbonate as an inexpensive and effective base, while significantly suppressing competing S<sub>N</sub>Ar pathways. The generality of the method was further demonstrated with simple aryl chlorides, which also underwent efficient hydroxylation. Mechanistic studies suggest that the reaction proceeds via a Cu(I)/Cu(III) catalytic cycle. Notably, the use of a sulfolane/water solvent system enabled high reactivity at a low catalyst loading, underscoring the practicality and scalability of this protocol.</p>","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"29 38","pages":""},"PeriodicalIF":2.8,"publicationDate":"2026-10-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"148836300","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
Piv2O-Mediated Esterification of Carboxylic Acids With Phenols Enabled by NMI Catalysis NMI催化下piv2o介导的羧酸与酚的酯化反应
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2026-10-13 Epub Date: 2026-08-31 DOI: 10.1002/ejoc.70825
Chenchen Qi, He You, Xiangsheng Xu, Xiaoqing Li
{"title":"Piv2O-Mediated Esterification of Carboxylic Acids With Phenols Enabled by NMI Catalysis","authors":"Chenchen Qi,&nbsp;He You,&nbsp;Xiangsheng Xu,&nbsp;Xiaoqing Li","doi":"10.1002/ejoc.70825","DOIUrl":"10.1002/ejoc.70825","url":null,"abstract":"<p>A green, stereoretentive esterification of carboxylic acids with phenols has been developed using N-methylimidazole (NMI) as the catalyst and pivalic anhydride (Piv<sub>2</sub>O) as the carboxylic acid activator. The reaction proceeds in ethyl acetate, exhibits broad functional group tolerance and minimal racemization, and generates pivalic acid as a readily separable byproduct. This mild, atom-economical strategy enables late-stage functionalization of pharmaceutical molecules, providing a sustainable route toward phenolic esters.</p>","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"29 38","pages":""},"PeriodicalIF":2.8,"publicationDate":"2026-10-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"148860781","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
Navigating the Radical Oxo‐Functionalization of Alkenes Toward Ketones 烯烃向酮基氧官能化的导航
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2026-10-12 DOI: 10.1002/ejoc.70840
Mattia Lepori, Luigi Dolcini, Alexander Bell, Joshua P. Barham
{"title":"Navigating the Radical Oxo‐Functionalization of Alkenes Toward Ketones","authors":"Mattia Lepori, Luigi Dolcini, Alexander Bell, Joshua P. Barham","doi":"10.1002/ejoc.70840","DOIUrl":"https://doi.org/10.1002/ejoc.70840","url":null,"abstract":"Ketones are ubiquitous structural motifs in pharmaceuticals, natural products, agrochemicals, and functional materials, as well as indispensable building blocks in organic synthesis. This outlines the design of efficient carbonyl‐forming strategies a crucial target in methodology development. Alongside classical textbook polar, two electron (2e <jats:sup>–</jats:sup> ) approaches, the so‐called single‐electron (1e <jats:sup>–</jats:sup> ) logic has established itself as the contemporary method of choice for direct, <jats:italic>de novo</jats:italic> construction of structurally complex ketones from simple commodity chemicals, under mild conditions. In this context, radical 1,2‐oxo‐functionalization of alkenes represents a valuable, practical platform to rapidly enhance molecular complexity <jats:italic>via</jats:italic> one‐pot difunctionalization of “flat” feedstock chemicals, thereby avoiding tedious isolation and purification of intermediates en route to target ketones. This Review surveys recent advances in radical alkene oxo‐functionalization, with a particular emphasis on methodologies enabled by thermal, transition metal‐catalyzed, photochemical, and electrochemical activations. The mechanistic principles governing the finely‐tuned orchestration of sequential vicinal CX (with X = carbon or heteroatom) and CO bond formations—including single‐electron transfer, hydrogen atom transfer, and radical polar crossover—are discussed alongside the diverse carbonyl oxygen atom sources employed, such as <jats:italic>tert</jats:italic> ‐butyl hydroperoxide (TBHP), dimethyl sulfoxide (DMSO), and molecular oxygen (O <jats:sub>2</jats:sub> ).","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"48 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2026-10-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149172639","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
Direct Synthesis of α‐Amino Ketones From Aldehydes and Amines via Photocatalytic In Situ Imines Hydroacylation 光催化原位亚胺氢酰化合成α -氨基酮的研究
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2026-10-12 DOI: 10.1002/ejoc.70906
Jingya Yang, Qi Dong, Haifang Xu, Hongyan Zhou
{"title":"Direct Synthesis of α‐Amino Ketones From Aldehydes and Amines via Photocatalytic In Situ Imines Hydroacylation","authors":"Jingya Yang, Qi Dong, Haifang Xu, Hongyan Zhou","doi":"10.1002/ejoc.70906","DOIUrl":"https://doi.org/10.1002/ejoc.70906","url":null,"abstract":"α‐Amino ketones have essential applications in pharmaceuticals and organic synthesis. The hydroacylation of imines is an attractive approach to access such valuable compounds. However, existing methods for hydroacylation with readily available aldehydes are highly dependent on the prepreparation of imines. Here, we report a photocatalytic protocol for synthesizing α‐amino ketones directly from aldehydes and amines. This one‐pot reaction proceeds smoothly in the presence of the photocatalyst tetrabutylammonium decatungstate (TBADT) and catalytic amounts of HBr. Aldehydes serve as both precursors for in situ imine formation and subsequent acylating agents. Hydrogen atom transfer (HAT) photocatalysis exhibits excellent two‐stage compatibility, allowing the transformation under mild and simple conditions. This strategy avoids the prepreparation and isolation of imines, providing an atom‐ and step‐economical route for the convenient synthesis of α‐amino ketones.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"85 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2026-10-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149172640","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
Enantioselective Conjugate Addition of Malononitriles to Enynes: A Stereodivergent Approach to Chiral Allenes 丙二腈对映选择性共轭加成：手性烯的立体发散方法
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2026-10-12 DOI: 10.1002/ejoc.70822
Martin Kamlar, Josef Panenka, Ivana Císařová, Jan Veselý
{"title":"Enantioselective Conjugate Addition of Malononitriles to Enynes: A Stereodivergent Approach to Chiral Allenes","authors":"Martin Kamlar, Josef Panenka, Ivana Císařová, Jan Veselý","doi":"10.1002/ejoc.70822","DOIUrl":"https://doi.org/10.1002/ejoc.70822","url":null,"abstract":"Quinine‐catalyzed enantioselective conjugate addition of malononitrile derivatives to enynes enables stereodivergent synthesis of trisubstituted chiral allenes. The reaction proceeds under mild conditions with good to excellent yields and high enantiomeric purities for both diastereoisomers. Optimization revealed that solvent and temperature strongly influence reactivity and stereochemical outcome. A broad range of aromatic and aliphatic enynes, as well as α‐substituted malononitriles, are well tolerated. The method is amenable to scale‐up and allows efficient derivatization of the resulting allenes into enantioenriched pyrazoles and furans, providing versatile building blocks for asymmetric synthesis.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"53 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2026-10-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149172638","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
Unorthodox Applications of Diethylaminosulfur Trifluoride and its Analogs in Organic Synthesis 二乙基氨基三氟化硫及其类似物在有机合成中的非正统应用
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2026-10-12 DOI: 10.1002/ejoc.70902
Chunliang Zhang, Rong Zhang, Teng Niu, Yang Su, Jingyuan Ma, Caiyun Gao, Xiaotong Lou, Yue Wang, Jiakuo Liu, Yanjun Ma, Hui Gao, Xinghui Zhang, Liping Jiang, Tianyu Yang
{"title":"Unorthodox Applications of Diethylaminosulfur Trifluoride and its Analogs in Organic Synthesis","authors":"Chunliang Zhang, Rong Zhang, Teng Niu, Yang Su, Jingyuan Ma, Caiyun Gao, Xiaotong Lou, Yue Wang, Jiakuo Liu, Yanjun Ma, Hui Gao, Xinghui Zhang, Liping Jiang, Tianyu Yang","doi":"10.1002/ejoc.70902","DOIUrl":"https://doi.org/10.1002/ejoc.70902","url":null,"abstract":"Diethylaminosulfur trifluoride (DAST) and related reagents are well‐established, commercially available nucleophilic fluorinating agents primarily known for their effectiveness in deoxyfluorination. Beyond their conventional applications, DAST‐type reagents have recently emerged as versatile tools for the synthesis of CF <jats:sub>3</jats:sub> S‐containing compounds, fluorinated benzoxathiin derivatives, and other non‐fluorine‐containing molecules that hold significant interest in pharmaceuticals, agrochemicals, and materials science. This review highlights the reactivity and expanding synthetic utility of DAST‐type reagents, with a particular emphasis on their unique roles in novel chemical transformations.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"10 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2026-10-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149172636","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 Functional Group Transpositions in Arenes and Heteroarenes 芳烃和杂芳烃的官能团转位研究进展
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2026-10-12 DOI: 10.1002/ejoc.70893
Chenwei Liang, Guanghui An
{"title":"Recent Advances in Functional Group Transpositions in Arenes and Heteroarenes","authors":"Chenwei Liang, Guanghui An","doi":"10.1002/ejoc.70893","DOIUrl":"https://doi.org/10.1002/ejoc.70893","url":null,"abstract":"Functional group transpositions in arenes and heteroarenes constitute a powerful tool in organic synthesis, enabling access to synthetically elusive compounds. Classical aromatic rearrangements, such as the Smiles, Claisen, and Bamberger reactions, allow positional reorganization but inevitably leave a residual substituent at the original ipso carbon, thereby precluding complete transfer. In contrast, a conceptually distinct yet underdeveloped class of transformations enables genuine positional transposition, in which a substituent undergoes net positional relocation within a pre‐existing or newly formed aromatic framework, thereby generating a different substitution pattern in the final aromatic product. This review delineates the conceptual boundaries among these processes and organizes previously scattered examples of functional group transposition, including transition‐metal‐enabled dissociation–recombination sequences, carbocation‐mediated processes, and multistep relay strategies, while also discussing closely related photochemical heterocycle isomerizations involving aromatic ring reconstruction as complementary strategies for positional editing. These advances highlight new opportunities to overcome intrinsic site‐selectivity limitations in aromatic synthesis.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"6 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2026-10-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149172635","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
Ammonium Chloride and Peroxide: A Metal‐Free Aqueous Strategy for Oxime Synthesis 氯化铵和过氧化物：一种无金属合成肟的水溶液策略
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2026-10-12 DOI: 10.1002/ejoc.70908
Junran Li, Linhong Yu, Weiqi Gao, Shiqun Xiang, Wei Zhang
{"title":"Ammonium Chloride and Peroxide: A Metal‐Free Aqueous Strategy for Oxime Synthesis","authors":"Junran Li, Linhong Yu, Weiqi Gao, Shiqun Xiang, Wei Zhang","doi":"10.1002/ejoc.70908","DOIUrl":"https://doi.org/10.1002/ejoc.70908","url":null,"abstract":"A metal‐free, aqueous protocol enables the synthesis of oximes from carbonyls using NH <jats:sub>4</jats:sub> Cl and H <jats:sub>2</jats:sub> O <jats:sub>2</jats:sub> . A radical mechanism involving in situ hydroxylamine generation bypasses the use of unstable salts. Monoethanolamine (MEA) serves as an essential additive, facilitating the conversion of 55 substrates with yields up to 93%. The practicality is underscored by a room‐temperature gram‐scale synthesis that requires no chromatographic purification, establishing a cost‐effective and environmentally benign alternative for oxime production.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"10 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2026-10-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149172637","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
Copper(II)/4‐Dimethylaminopyridine‐Mediated Oxidative Cyclization in Low‐Melting Mixtures: Access to Cyclopropane‐Fused Aza‐Heterocycles 低熔点混合物中铜(II)/4 -二甲氨基吡啶介导的氧化环化：获得环丙烷-融合的Aza -杂环
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2026-10-07 DOI: 10.1002/ejoc.70883
Nemichand,Vilas M. Awchar,Sundarababu Baskaran
{"title":"Copper(II)/4‐Dimethylaminopyridine‐Mediated Oxidative Cyclization in Low‐Melting Mixtures: Access to Cyclopropane‐Fused Aza‐Heterocycles","authors":"Nemichand,Vilas M. Awchar,Sundarababu Baskaran","doi":"10.1002/ejoc.70883","DOIUrl":"https://doi.org/10.1002/ejoc.70883","url":null,"abstract":"A simple and efficient one‐pot approach has been developed for the stereoselective synthesis of 3‐azabicyclo[n.1.0]alkane derivatives, employing a low–melting mixture (LMM) composed of choline chloride (ChCl) and N , N ‐dimethylurea (DMU). This green and sustainable protocol facilitates the intramolecular oxidative cyclization of N ‐allyl malonamates to afford a diverse array of cyclopropane‐fused aza‐heterocycles in excellent yields. Furthermore, the utility of this methodology is exemplified in the concise and efficient synthesis of the antidepressant drug candidate GSK1360707.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"24 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2026-10-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149088494","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
Electrochemical Synthesis of Sulfur(VI) Compounds 硫（VI）化合物的电化学合成
IF 2.8 3区 化学
European Journal of Organic Chemistry Pub Date : 2026-10-06 DOI: 10.1002/ejoc.70852
Karim Ullah, Stavros Boukouvalas, Jan Evens, Joachim Demaerel, Wim M. De Borggraeve
{"title":"Electrochemical Synthesis of Sulfur(VI) Compounds","authors":"Karim Ullah, Stavros Boukouvalas, Jan Evens, Joachim Demaerel, Wim M. De Borggraeve","doi":"10.1002/ejoc.70852","DOIUrl":"https://doi.org/10.1002/ejoc.70852","url":null,"abstract":"Electrochemical synthesis is emerging as a green and versatile platform for sulfur(VI) chemistry, using electric current to replace or minimize the use of stoichiometric oxidants and to access high‐valent sulfur under generally mild conditions. This review highlights recent (2020–2025) electrochemical methods for the preparation of key S(VI) motifs, including sulfonyl fluorides, sulfones, sulfonate esters, thiosulfonates, sulfoximines, and sulfonimidoyl fluorides. Emphasis is placed on the transformation of simple <jats:italic>S</jats:italic> ‐containing precursors in straightforward undivided or flow cell setups under mild conditions, highlighting electrosynthesis as a sustainable tool for constructing and editing sulfur(VI) scaffolds relevant to medicinal chemistry, agrochemicals, and materials science.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"23 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2026-10-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149087387","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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