European Journal of Organic Chemistry最新文献_第9页

Direct Conversion of Aryl Iodides Into Benzylamines by Aminomethylation: Reaction Scope, Mechanistic Studies, and Applications 芳基碘化物经氨基甲基化直接转化为苄胺：反应范围、机理研究及应用

IF 2.8 3区化学

European Journal of Organic Chemistry Pub Date : 2026-10-01 Epub Date: 2026-08-20 DOI: 10.1002/ejoc.70787

Abhijit Sen, Atsuya Muranaka, Yu Hatakenaka, Aya Ohno, Yoichi M. A. Yamada

{"title":"Direct Conversion of Aryl Iodides Into Benzylamines by Aminomethylation: Reaction Scope, Mechanistic Studies, and Applications","authors":"Abhijit Sen, Atsuya Muranaka, Yu Hatakenaka, Aya Ohno, Yoichi M. A. Yamada","doi":"10.1002/ejoc.70787","DOIUrl":"10.1002/ejoc.70787","url":null,"abstract":"<p>Despite the high utility and value of benzylamines and their derivatives, their synthesis is hindered by a limited substrate availability and nonreusable transition-metal catalysts. To that end, this study develops an aminomethylation strategy using aryl iodides and formamides while examining the substrate scope and underlying mechanism for synthesizing benzylamines under parts-per-million-level (65 ppm) reusable palladium catalysis. This method can accommodate a wide range of substrates, including electron-rich and electron-deficient aryl, polyaryl, and heteroaryl iodides. Similarly, various formamide derivatives yield aminomethylated products. This aminomethylation strategy is used to directly synthesize biologically active molecules, such as a rivastigmine analog, and natural products, e.g., gramine. In addition, tryptamine, a serotonin receptor, and diindolylmethane, a metabolite, are successfully produced by derivatizing the aminomethylated products. Isotope-labeling experiments indicate that formamide derivatives were precursors for the reducing agent, in addition to providing both amines and carbon. A plausible catalytic pathway is proposed based on isotope-labeling experiments and density functional theory calculations, providing insights for future research and new applications in organic synthesis and medicinal chemistry.</p>","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"29 37","pages":""},"PeriodicalIF":2.8,"publicationDate":"2026-10-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/ejoc.70787","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"148768591","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}

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Exploiting Biocatalysis for the Scalable Synthesis of Enantiopure γ-Hydroxynitrile Building Blocks 利用生物催化可扩展合成对映纯γ -羟基腈构建块

IF 2.8 3区化学

European Journal of Organic Chemistry Pub Date : 2026-10-01 Epub Date: 2026-08-25 DOI: 10.1002/ejoc.70782

Benjamin Baumert, Kathryn Yeow, Roi Boris Tchuemmogne Tchuente, Adam Cruise, Christopher Thomas, Thomas Bayer, Uwe T. Bornscheuer, Marcus Baumann

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Ring‐Opening Cyclization (ROC) of Aziridines With 2‐(2‐Bromophenyl)‐1 H ‐Benzimidazoles: Rotamer Analysis and Synthesis of Benzimidazole‐Fused 1,4‐Benzodiazepine 叠氮嘧啶与2‐（2‐溴苯基）‐1 H‐苯并咪唑的开环环化（ROC）：苯并咪唑-融合1,4‐苯并二氮卓的旋转体分析和合成

IF 2.8 3区化学

European Journal of Organic Chemistry Pub Date : 2026-10-01 DOI: 10.1002/ejoc.70879

Suraj Kashyap, Bharat Singh, Prabodh Ranjan, Shishir Singh, Ajit K. Gupta, Manas K. Ghorai

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Hydrosilylation of Nitrones With Trichlorosilane: Preparation of Hydroxylamines 硝基酮与三氯硅烷的硅氢化反应：羟胺的制备

IF 2.8 3区化学

European Journal of Organic Chemistry Pub Date : 2026-10-01 Epub Date: 2026-08-25 DOI: 10.1002/ejoc.70812

Yifan Li, Kexin Su, Yuxi Guo, Xiaohua Lei, Zixiang Wang, Qiang Wang, Ju Guo, Yongsheng Zheng

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c-Met/DDR1 Dual-Target Tyrosine Kinase Inhibitor Featuring an Imidazo[1,2-A]pyridine Core c‐Met/DDR1双靶点酪氨酸激酶抑制剂，具有咪唑[1,2‐A]吡啶核心

IF 2.8 3区化学

European Journal of Organic Chemistry Pub Date : 2026-10-01 Epub Date: 2026-08-23 DOI: 10.1002/ejoc.70796

Jiaji Zhao, Wei Xu, Yanshuang Lin, Jiapeng Sun, Hua Cao

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Strategic Formation of Indoles Using Phenyl Hydrazine as a Key Reagent 以苯肼为关键试剂的吲哚合成研究

IF 2.8 3区化学

European Journal of Organic Chemistry Pub Date : 2026-09-30 DOI: 10.1002/ejoc.70878

Amit Kumar Verma, Anuj Yadav, Devendra Singh Negi, Surendra Puri

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Efficient Synthesis of Cannabinoid Acids 大麻素酸的高效合成

IF 2.8 3区化学

European Journal of Organic Chemistry Pub Date : 2026-09-30 DOI: 10.1002/ejoc.70860

Ryosuke Arai, Hikari Nishiguchi, Kayo Nakamura, Hiroko Abe, Akihiko Ishida, Manabu Tokeshi, Kyohei Higashi, Akiyoshi Saitoh, Hideyo Takahashi

{"title":"Efficient Synthesis of Cannabinoid Acids","authors":"Ryosuke Arai, Hikari Nishiguchi, Kayo Nakamura, Hiroko Abe, Akihiko Ishida, Manabu Tokeshi, Kyohei Higashi, Akiyoshi Saitoh, Hideyo Takahashi","doi":"10.1002/ejoc.70860","DOIUrl":"https://doi.org/10.1002/ejoc.70860","url":null,"abstract":"Cannabinoid acids are the carboxylic acid precursors of cannabinoids, which are present in high abundance in fresh cannabis plants. During heating and storage, cannabinoid acids undergo decarboxylation to produce the corresponding cannabinoids. Cannabinoid acids have been prepared through the reaction of cannabinoids with methyl magnesium carbonate (MMC); however, this method has a limited substrate scope, and Δ 9 ‐tetrahydrocannabinolic acid cannot be produced using this approach. In this study, an alternative synthesis of cannabinoid acids was developed based on an O → C acyl rearrangement. Specifically, this strategy involved regioselective bromination followed by halogen–lithium exchange and intramolecular nucleophilic addition, which led to successful carboxylation. The key reaction was identified as a regioselective bromination using cyclopentyl methyl ether as the optimal solvent, affording the 2‐brominated product in high yield. This rearrangement strategy enabled the efficient synthesis of cannabinoid acids from cannabinoids.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"36 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2026-09-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149085942","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

Photochemical Synthesis of Dihydropyrido[1,2‐ a :3,4‐ b ′]diindole Derivatives 二氢吡啶[1,2‐a:3,4‐b ']二吲哚衍生物的光化学合成

IF 2.8 3区化学

European Journal of Organic Chemistry Pub Date : 2026-09-30 DOI: 10.1002/ejoc.70882

Kai‐Rong Chen, Yin‐Jiu Zhao, Shuang Chen, Jun‐Nan Xu, Qin Ma, Yan‐Chuan Gong, Jie Zhang, Liang Guo

{"title":"Photochemical Synthesis of Dihydropyrido[1,2‐ a :3,4‐ b ′]diindole Derivatives","authors":"Kai‐Rong Chen, Yin‐Jiu Zhao, Shuang Chen, Jun‐Nan Xu, Qin Ma, Yan‐Chuan Gong, Jie Zhang, Liang Guo","doi":"10.1002/ejoc.70882","DOIUrl":"https://doi.org/10.1002/ejoc.70882","url":null,"abstract":"Herein, we report a photochemical method for the intramolecular cyclization of N‐(substituted benzoyl)‐1‐substituted‐1,2,3,4‐tetrahydro‐β‐carbolines. This transformation relies on photoexcitation of the substrate itself in the absence of external photocatalysts, with catalytic p ‐toluenesulfonic acid (PTSA) facilitating the cyclization process. This reaction provides a straightforward and practical approach for the synthesis of dihydro‐pyrido[1,2‐ a :3,4‐ b ′]diindoles. We investigate the substrate scope by varying substituents at the R 2 and R 9 positions of the starting materials. A variety of dihydro‐pyrido[1,2‐ a :3,4‐ b ′]diindoles were successfully synthesized in moderate to excellent yields (up to 84%). Substrates bearing alkyl, aryl, polysubstituted, and fused‐ring moieties are well tolerated. Furthermore, the synthetic practicability of this protocol is validated by a gram‐scale reaction.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"5 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2026-09-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149085938","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}

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Advances in NN Bond Formation: Mechanistic Diversity and Emerging Catalytic Strategies 氮-氮键形成的研究进展：机制多样性和新兴的催化策略

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European Journal of Organic Chemistry Pub Date : 2026-09-30 DOI: 10.1002/ejoc.70839

Subhajit Chakraborty, Afsana Pervin, Nanda D. Paul

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[Metal–(Nitrogen and/or OxygenPhosphorus‐Based Ligand)]‐Catalyzed Asymmetric Hydrogenation of β‐Amido β‐Substituted Acrylic Esters and Phosphoro Analogs: A Practical Literature Overview [金属-（氮-和/或氧-磷-基配体）]-催化β -氨基β -取代丙烯酸酯和磷类似物的不对称氢化：实用文献综述

IF 2.8 3区化学

European Journal of Organic Chemistry Pub Date : 2026-09-30 DOI: 10.1002/ejoc.70565

Marko Jeran, Arnald Grabulosa, Barbara Mohar, Michel Stephan

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