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Urea as an Amine Source to Synthesize Primary Aromatic Amines via Nickel‐Mediated C−H Amination 尿素作为胺源通过镍介导的C−H胺化反应合成伯胺芳胺
IF 2.5 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-05-21 DOI: 10.1002/ejoc.202500087
Jiahui Du , Xun Yang , Haiyan Li , Yuxuan Xiao , Ying Yin , Junying Wen , Dr. Chan Yang , Prof. Dr. Ze Tan , Dr. Lin Yu
{"title":"Urea as an Amine Source to Synthesize Primary Aromatic Amines via Nickel‐Mediated C−H Amination","authors":"Jiahui Du ,&nbsp;Xun Yang ,&nbsp;Haiyan Li ,&nbsp;Yuxuan Xiao ,&nbsp;Ying Yin ,&nbsp;Junying Wen ,&nbsp;Dr. Chan Yang ,&nbsp;Prof. Dr. Ze Tan ,&nbsp;Dr. Lin Yu","doi":"10.1002/ejoc.202500087","DOIUrl":"10.1002/ejoc.202500087","url":null,"abstract":"<div><div>A straightforward and efficient method has been developed for the transformation of aromatic C<sub>Ar</sub>−H bond into C<sub>Ar</sub>−NH₂ via nickel‐mediated C−H activation, eliminating the need for additional protection and deprotection steps. This strategy employs 8‐aminoquinoline as a directing group and urea as the nitrogen source, a non‐toxic, inexpensive, and stable bulk chemical. The reaction exhibits high selectivity, exclusively yielding mono‐aminated primary aromatic amines. Furthermore, the protocol is tolerant of a wide range of substrates with various functional groups, producing the corresponding ortho‐aminobenzamides in yields ranging from 38 % to 73 %. The preliminary results indicate the C−H bond cleavage is likely the rate‐determining step in the reaction.</div></div>","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"28 17","pages":"Article e202500087"},"PeriodicalIF":2.5,"publicationDate":"2025-05-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143393828","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 Vinyl Boronates from Aldehydes and Ketones by Peterson Olefination: Investigation of the Peterson/Boron‐Wittig Chemoselectivity 彼得森烯烃法合成硼酸乙烯基：彼得森/硼Wittig化学选择性的研究
IF 2.5 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-05-21 DOI: 10.1002/ejoc.202500033
Julien Janssens , Guillaume Berionni , Raphaël Robiette
{"title":"Synthesis of Vinyl Boronates from Aldehydes and Ketones by Peterson Olefination: Investigation of the Peterson/Boron‐Wittig Chemoselectivity","authors":"Julien Janssens ,&nbsp;Guillaume Berionni ,&nbsp;Raphaël Robiette","doi":"10.1002/ejoc.202500033","DOIUrl":"10.1002/ejoc.202500033","url":null,"abstract":"<div><div>We report our results on the development of the Peterson olefination using <em>gem</em>‐borylsilylmethane derivatives to synthesize di‐ and tri‐substituted vinyl boronates. We show that the electronic properties of the carbonyl partner have no effect on the Peterson/boron‐Wittig chemoselectivity whereas the nature of the silane group plays an important role. A DFT study helps explain observed reactivity, chemoselectivity and stereoseletivity</div></div>","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"28 17","pages":"Article e202500033"},"PeriodicalIF":2.5,"publicationDate":"2025-05-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143192193","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 the α‐Hydrazination (α‐Amination) of Carbonyl Compounds 羰基化合物α-肼化（α-胺化）研究进展
IF 2.5 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-05-21 DOI: 10.1002/ejoc.202500049
Dina Scarpi , Samuele Visi , Ernesto G. Occhiato
{"title":"Recent Advances in the α‐Hydrazination (α‐Amination) of Carbonyl Compounds","authors":"Dina Scarpi ,&nbsp;Samuele Visi ,&nbsp;Ernesto G. Occhiato","doi":"10.1002/ejoc.202500049","DOIUrl":"10.1002/ejoc.202500049","url":null,"abstract":"<div><div>The electrophilic α‐hydrazination (generally referred to as α‐amination) of carbonyl compounds with dialkyl azodicarboxylates is a powerful approach for the preparation of synthetically useful intermediates such as α‐amino aldehydes and ketones, α‐amino acids, and β‐amino alcohols. Many methods for the enantioselective α‐hydrazination have been published in the past and many new approaches have been disclosed in the last decade that deal with previously unresolved issues such as the direct enantioselective α‐hydrazination of α‐branched ketones. The enantioselective α‐hydrazination is the field where most significant advances have been attained thanks to new approaches, catalysts and techniques. With this review we intend to cover the literature that appeared between 2015 and 2024. We will classify the various methods according to the strategies for the enantioselective formation of the new C−N bond, mainly based on the formation of chiral enamines, enols and enolates. Miscellaneous methods are grouped at the end of the review. Where relevant, the application of α‐hydrazino carbonyl compounds to the synthesis of target molecules will also be illustrated.</div></div>","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"28 17","pages":"Article e202500049"},"PeriodicalIF":2.5,"publicationDate":"2025-05-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143385880","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
On the Reactivity of Bisphosphirane‐Fused Anthracene towards Dichalcogenide Bonds, IPr Carbene, 2,6‐Diisopropylphenyl Isocyanide and Trimethylsilyl Azide 双磷烷-融合蒽对二氯键、IPr卡宾、2,6 -二异丙基苯基异氰化物和三甲基硅基叠氮化物的反应性
IF 2.5 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-05-21 DOI: 10.1002/ejoc.202500071
Qing Luo , Tingting Liu , Linlin Huang , Prof. Dr. Qianli Li , Prof. Dr. Wei Lu
{"title":"On the Reactivity of Bisphosphirane‐Fused Anthracene towards Dichalcogenide Bonds, IPr Carbene, 2,6‐Diisopropylphenyl Isocyanide and Trimethylsilyl Azide","authors":"Qing Luo ,&nbsp;Tingting Liu ,&nbsp;Linlin Huang ,&nbsp;Prof. Dr. Qianli Li ,&nbsp;Prof. Dr. Wei Lu","doi":"10.1002/ejoc.202500071","DOIUrl":"10.1002/ejoc.202500071","url":null,"abstract":"<div><div>The development of phosphinidene precursors capable of releasing free phosphinidenes holds great potential in exploiting their reactivity with small molecules and enthalpically strong bonds. We report the facile cleavage of dichalcogenide bonds, including S−S, Se−Se and Te−Te bonded complexes over the phosphorus center of a bisphosphirane‐fused anthracene (<strong>1</strong>), which produces a variety of phosphonodichalcogenides (<strong>2</strong>‐<strong>4</strong>). We also show the ambiphilic nature of <strong>1</strong>. The reaction of <strong>1</strong> with nucleophiles, such as 1,3‐bis(<em>iso</em>propyl)imidazol‐2‐ylidene (I<em>i</em>Pr) and 2,6‐diisopropylphenyl isocyanide (DipNC) gives a phosphinidene adduct of I<em>i</em>Pr and a 1‐phospha‐3‐azaallene, respectively. Treatment of <strong>1</strong> with trimethylsilyl azide (TMSN<sub>3</sub>) affords an iminophosphanide, manifesting the nucleophilic nature of <strong>1</strong>. These compounds were fully characterized by single‐crystal X‐ray diffraction (SC‐XRD) and spectroscopic analysis.</div></div>","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"28 17","pages":"Article e202500071"},"PeriodicalIF":2.5,"publicationDate":"2025-05-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143393135","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
NHC‐Free Ketone Synthesis via Radical Coupling Mechanisms 自由基偶联机制下无nhc酮的合成
IF 2.5 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-05-21 DOI: 10.1002/ejoc.202500011
Lifeng Wang , Yuxing Cai , Yong Huang
{"title":"NHC‐Free Ketone Synthesis via Radical Coupling Mechanisms","authors":"Lifeng Wang ,&nbsp;Yuxing Cai ,&nbsp;Yong Huang","doi":"10.1002/ejoc.202500011","DOIUrl":"10.1002/ejoc.202500011","url":null,"abstract":"<div><div>Ketone synthesis via radical coupling mechanisms has recently gained significant attention. Traditionally, these methods have relied on N‐heterocyclic carbenes (NHCs) to generate the key ketyl radical intermediate, either through single‐electron reduction of acyl azolium or single‐electron oxidation involving the Breslow intermediate. In this report, we introduce a novel photoredox protocol that directly generates ketyl radicals from stable acyl imidazoles without the need for NHCs. This approach not only simplifies the process, but also demonstrates broad tolerance for various alkyl radical substrates. Additionally, it can be extended to facilitate relay‐radical coupling reactions.</div></div>","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"28 17","pages":"Article e202500011"},"PeriodicalIF":2.5,"publicationDate":"2025-05-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143124960","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
Fluorine‐Containing 6‐Azabicyclo[3.1.1]heptanes: Bicyclic Piperidine Analogs for Drug Discovery 含氟6-阿扎比环[3.1.1]庚烷：用于药物发现的双环哌啶类似物
IF 2.5 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-05-21 DOI: 10.1002/ejoc.202500022
Dr. Anton V. Chernykh , Dr. Oleksandr S. Liashuk , Dr. Anastasiia M. Hurieva , Dmytro Lesyk , Yuliia Holota , Dr. Petro Borysko , Prof. Dr. Svitlana V. Shishkina , Prof. Dr. Dmytro M. Volochnyuk , Prof. Dr. Oleksandr O. Grygorenko
{"title":"Fluorine‐Containing 6‐Azabicyclo[3.1.1]heptanes: Bicyclic Piperidine Analogs for Drug Discovery","authors":"Dr. Anton V. Chernykh ,&nbsp;Dr. Oleksandr S. Liashuk ,&nbsp;Dr. Anastasiia M. Hurieva ,&nbsp;Dmytro Lesyk ,&nbsp;Yuliia Holota ,&nbsp;Dr. Petro Borysko ,&nbsp;Prof. Dr. Svitlana V. Shishkina ,&nbsp;Prof. Dr. Dmytro M. Volochnyuk ,&nbsp;Prof. Dr. Oleksandr O. Grygorenko","doi":"10.1002/ejoc.202500022","DOIUrl":"10.1002/ejoc.202500022","url":null,"abstract":"<div><div>Convenient synthetic approaches to a series of fluorinated bicyclic piperidine analogs (including 3‐fluoro‐, 3,3‐difluoro‐, 3‐carboxy‐3‐fluoro‐, and 3‐trifluoromethyl‐substituted 6‐azabicyclo[3.1.1]heptanes) were proposed. Using commercially available fluorination agents, the target building blocks were prepared in gram to decagram scale in a single run. Evaluation of p<em>K</em><sub>a</sub> and Log<em>P</em> values revealed the importance of the fluorine‐containing substituent and methylene bridge relative disposition for the compound's physicochemical properties. Analysis of molecular structure using the exit vector plot (EVP) approach revealed negligible change in molecules conformation upon fluorination.</div></div>","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"28 17","pages":"Article e202500022"},"PeriodicalIF":2.5,"publicationDate":"2025-05-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143371493","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 Hydroxyselenenylation of Multifunctional Homoallyl Amines and Ethers 多功能化全烯丙基胺和醚的电化学羟基硒化反应
IF 2.5 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-05-21 DOI: 10.1002/ejoc.202500075
Dr. Wen Xia , Tongtong Liu , Prof. Zhipeng Ruan , Pei Tian , Wenxuan Yu , Ass. Prof. Xiaohui Zhang , Prof. Dr. Yan Xiong
{"title":"Electrochemical Hydroxyselenenylation of Multifunctional Homoallyl Amines and Ethers","authors":"Dr. Wen Xia ,&nbsp;Tongtong Liu ,&nbsp;Prof. Zhipeng Ruan ,&nbsp;Pei Tian ,&nbsp;Wenxuan Yu ,&nbsp;Ass. Prof. Xiaohui Zhang ,&nbsp;Prof. Dr. Yan Xiong","doi":"10.1002/ejoc.202500075","DOIUrl":"10.1002/ejoc.202500075","url":null,"abstract":"<div><div>A series of β‐hydroxyselenides from reactive N‐homoallyl(hetero)arylamines and O‐homoallyl(hetero)arylethers were effectively synthesized with high to excellent yields under electrolysis. The profiles of mild conditions, simple operation, short time, free of oxidants and transition metals, and good compatibilities of substrates render this methodology greener and potentially synthetic value in producing application.</div></div>","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"28 17","pages":"Article e202500075"},"PeriodicalIF":2.5,"publicationDate":"2025-05-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143462708","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
One‐Step Synthesis of a 2,2’‐Directly‐Linked Perylene Dimer from a 2,5,8,11‐Tetraborylated Perylene 由2,5,8,11四硼化苝一步合成2,2 ' -直接连接的苝二聚体
IF 2.5 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-05-21 DOI: 10.1002/ejoc.202500042
Ryuichi Fujita , Miho Hirakawa , Dr. Ryoko Oyama , Dr. Kyohei Matsuo , Dr. Hironobu Hayashi , Dr. Mitsuaki Yamauchi , Prof. Dr. Hiroko Yamada , Prof. Dr. Naoki Aratani
{"title":"One‐Step Synthesis of a 2,2’‐Directly‐Linked Perylene Dimer from a 2,5,8,11‐Tetraborylated Perylene","authors":"Ryuichi Fujita ,&nbsp;Miho Hirakawa ,&nbsp;Dr. Ryoko Oyama ,&nbsp;Dr. Kyohei Matsuo ,&nbsp;Dr. Hironobu Hayashi ,&nbsp;Dr. Mitsuaki Yamauchi ,&nbsp;Prof. Dr. Hiroko Yamada ,&nbsp;Prof. Dr. Naoki Aratani","doi":"10.1002/ejoc.202500042","DOIUrl":"10.1002/ejoc.202500042","url":null,"abstract":"<div><div>One‐step Suzuki‐Miyaura cross‐coupling reaction of 2,5,8,11‐tetra‐borylated perylene with 2,6‐bis(trifluoromethyl)bromo‐benzene gave 2,2’‐linked perylene dimer for the first time in 7.3 % yield under the standard conditions. The single‐crystal X‐ray structure exhibits three independent dimers in the unit cell, reflecting the low rotational energy around 2,2’‐linkage. Excited state properties of 2,2’‐dimer were compared with the corresponding 3,3’‐linked congener. The facile synthetic method developed in this study could be a general route to access polycyclic aromatic hydrocarbon oligomers linked at less reactive positions.</div></div>","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"28 17","pages":"Article e202500042"},"PeriodicalIF":2.5,"publicationDate":"2025-05-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143470691","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
Three‐Component Cycloadditions to Prepare Isooxazoline‐Fused Furo[3,2‐b]quinolines 三组分环加成制备异恶唑-熔接呋喃[3,2-b]喹啉
IF 2.5 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-05-21 DOI: 10.1002/ejoc.202500007
Chun‐Yu Nong , Xiu‐Qing Mo , Jin‐He Zhao , Lu Lei , Lu Ma , Prof. Dong‐Liang Mo
{"title":"Three‐Component Cycloadditions to Prepare Isooxazoline‐Fused Furo[3,2‐b]quinolines","authors":"Chun‐Yu Nong ,&nbsp;Xiu‐Qing Mo ,&nbsp;Jin‐He Zhao ,&nbsp;Lu Lei ,&nbsp;Lu Ma ,&nbsp;Prof. Dong‐Liang Mo","doi":"10.1002/ejoc.202500007","DOIUrl":"10.1002/ejoc.202500007","url":null,"abstract":"<div><div>A variety of isooxazoline‐fused furo[3,2‐b]quinolines containing four stereocenters were prepared in 40 %‐87 % yields with high regioselectivity and diastereoselectivity. The control experimental results revealed that the reaction underwent in the order of [4+2] cycloaddition and sequential [3+2] cycloaddition between aza‐<em>ortho</em>‐quinone methides (ao‐QM) generated from 2‐chloromethyl anilines, furans, and nitrile <em>N</em>‐oxides generated from hydroxamoyl chlorides. The present method features mild reaction conditions, broad substrate scope, high diastereoselectivity of four stereocenters, and novel scaffolds of isooxazoline‐fused furo[3,2‐b]quinolines.</div></div>","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"28 17","pages":"Article e202500007"},"PeriodicalIF":2.5,"publicationDate":"2025-05-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143539333","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
One‐Pot Synthesis of Fluorinated Pyrimidine Derivatives from Aldehydes by Photocatalytic α‐Perfluoroalkenylation 光催化α-全氟烷基化一锅法合成醛类氟化嘧啶衍生物
IF 2.5 3区 化学
European Journal of Organic Chemistry Pub Date : 2025-05-21 DOI: 10.1002/ejoc.202500047
Yu‐Jun Zhu , Constantin Czekelius
{"title":"One‐Pot Synthesis of Fluorinated Pyrimidine Derivatives from Aldehydes by Photocatalytic α‐Perfluoroalkenylation","authors":"Yu‐Jun Zhu ,&nbsp;Constantin Czekelius","doi":"10.1002/ejoc.202500047","DOIUrl":"10.1002/ejoc.202500047","url":null,"abstract":"<div><div>A straightforward, operationally simple and inexpensive one‐pot synthesis of substituted 4‐perfluoroalkyl‐pyrimidine derivatives is reported. Employing triphenylphosphine as a photocatalyst and an additional imidazolidinone organocatalyst, aldehydes undergo α‐perfluoroalkenylation giving highly electron‐deficient enals, which form the heterocycle upon condensation with a guanidinium salt. The method tolerates many functional groups and gives the corresponding products in up to 84 % yield over both steps.</div></div>","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"28 17","pages":"Article e202500047"},"PeriodicalIF":2.5,"publicationDate":"2025-05-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143027031","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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