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Rh(III)-Catalyzed, N-Amino-Directed C-H Coupling with α-Cyano-α-Diazoesters for the Synthesis of 3-Aminocinnoline-4-Carboxylates. Rh（III）催化n -氨基导向C-H与α-氰基-α-重氮酯偶联合成3-氨基氨基糖-4-羧酸酯。
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-10-18 DOI: 10.1021/acs.joc.5c02197
Renpeng Zhou,Xuanzhen Han,Wenjie Yue,Zhixin Wang,Jin Zhu
{"title":"Rh(III)-Catalyzed, N-Amino-Directed C-H Coupling with α-Cyano-α-Diazoesters for the Synthesis of 3-Aminocinnoline-4-Carboxylates.","authors":"Renpeng Zhou,Xuanzhen Han,Wenjie Yue,Zhixin Wang,Jin Zhu","doi":"10.1021/acs.joc.5c02197","DOIUrl":"https://doi.org/10.1021/acs.joc.5c02197","url":null,"abstract":"Reactivity-propagating synthesis is proposed herein as a transformative synthetic practice, with both reactant reactivity and product inner reactivity programmed into the synthetic design and survival of product inner reactivity as the central goal. Rh(III)-catalyzed, N-amino-directed C-H coupling with α-cyano-α-diazoesters has been developed for the synthesis of 3-aminocinnoline-4-carboxylates. This synthetic methodology features the survival of the product inner reactivity of two heteroatom sites of nitrogen as well as amino and ester groups, allowing versatile entry into varied open-chain and ring topology structures.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"45 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-10-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145311670","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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
The Development of Stereoselective Substrate and Reagent-Controlled Lithiation-Borylation Chemistry. 立体选择性底物和试剂控制锂-硼化化学的发展。
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-10-17 DOI: 10.1021/acs.joc.5c01854
Yannick Linne,Maike Birkner,Daniel Lücke,Jan Flormann,Kjeld Gerdes,Giada Tedesco,Gaia Stojanovic,Tom Jentsch,Birk Jäger,Kevin Bajerke,Jörg August Becker,Markus Kalesse
{"title":"The Development of Stereoselective Substrate and Reagent-Controlled Lithiation-Borylation Chemistry.","authors":"Yannick Linne,Maike Birkner,Daniel Lücke,Jan Flormann,Kjeld Gerdes,Giada Tedesco,Gaia Stojanovic,Tom Jentsch,Birk Jäger,Kevin Bajerke,Jörg August Becker,Markus Kalesse","doi":"10.1021/acs.joc.5c01854","DOIUrl":"https://doi.org/10.1021/acs.joc.5c01854","url":null,"abstract":"Allylic alcohols are a privileged motif in polyketide-based natural product synthesis, and new methods that access them in a stereoselective fashion are highly sought after. Toward this goal, we found that the use of chiral polyketide fragments allows for performing the Hoppe-Matteson-Aggarwal rearrangement in the absence of sparteine with high yields and diastereoselectivities, rendering this protocol a highly valuable alternative to existing methods. Various stereodyads and -triads bearing different protecting and directing groups were investigated to determine their substrate induction. The mostly strong inherent induction was attributed to either steric or a combination of steric and electronic effects. The stereochemical outcome could be explained by (DFT-based) conformational analysis and a Felkin-like model, allowing guidance flowcharts to be created for the substrate- and reagent-controlled lithiation-borylation chemistry.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"44 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-10-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145311675","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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
Donor–Acceptor-Substituted 5-Azaazulenes Donor-Acceptor-Substituted 5-Azaazulenes
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-10-17 DOI: 10.1021/acs.joc.5c01663
Enikő Meiszter, Gábor Turczel, András Stirling, Péter Pál Fehér, Gábor London
{"title":"Donor–Acceptor-Substituted 5-Azaazulenes","authors":"Enikő Meiszter, Gábor Turczel, András Stirling, Péter Pál Fehér, Gábor London","doi":"10.1021/acs.joc.5c01663","DOIUrl":"https://doi.org/10.1021/acs.joc.5c01663","url":null,"abstract":"The synthesis of 5-azaazulenes with both donor and acceptor substituents on their seven-membered rings is reported through the ring expansion of stable azapentalene derivatives upon reaction with dimethyl acetylenedicarboxylate. Regioisomeric products were obtained and characterized. The mechanism of the transformation and the excited state energy levels of the products were studied computationally, suggesting that these structures can be entry points to chromophore design for organic photonics applications.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"5 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-10-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145306323","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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
Iron-Catalyzed Selective Sulfonylation of Alkenes by Sulfonyl Fluorides. 铁催化的氟磺酰基烯烃选择性磺化反应。
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-10-17 DOI: 10.1021/acs.joc.5c01566
Tong-Tong Zhao,Zi-Yu Liu,Si-Han Zheng,Shu-Han Wang,Ke-Yu Li,Qiang Bian,Da-Zhen Xu
{"title":"Iron-Catalyzed Selective Sulfonylation of Alkenes by Sulfonyl Fluorides.","authors":"Tong-Tong Zhao,Zi-Yu Liu,Si-Han Zheng,Shu-Han Wang,Ke-Yu Li,Qiang Bian,Da-Zhen Xu","doi":"10.1021/acs.joc.5c01566","DOIUrl":"https://doi.org/10.1021/acs.joc.5c01566","url":null,"abstract":"Herein, we report an iron-catalyzed approach for the generation of sulfonyl radicals from readily available bulk raw material sulfonyl chlorides and selective sulfonylation of alkenes for the synthesis of β-keto sulfones and vinyl sulfones depending on the reaction conditions. Under mild aerobic oxidation conditions in ethanol, β-keto sulfones were obtained via C(sp2)-C bond cleavage, while under argon protection in hexafluoroisopropanol, vinyl sulfones were formed. Mechanism studies reveal that iron salts play the role of hitting two birds with one stone, involving hydrogen atom transfer (HAT) and single-electron transfer (SET) processes.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"32 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-10-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145305368","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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 Oxidative Dehydrogenative Thioacylation of N-Heterocycles with CS2 and Amines. n -杂环与CS2和胺的电化学氧化脱氢硫酰化反应。
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-10-17 DOI: 10.1021/acs.joc.5c01996
Lin Li,Yanan Li,Jinsong Hu,Chenpei Yang,Jianan Sun,Peng Qian
{"title":"Electrochemical Oxidative Dehydrogenative Thioacylation of N-Heterocycles with CS2 and Amines.","authors":"Lin Li,Yanan Li,Jinsong Hu,Chenpei Yang,Jianan Sun,Peng Qian","doi":"10.1021/acs.joc.5c01996","DOIUrl":"https://doi.org/10.1021/acs.joc.5c01996","url":null,"abstract":"An electrochemical strategy is developed for valorizing sulfur-rich carbon disulfide (CS2) through thioacylation of nitrogen-containing heterocycles including carbazole and indole derivatives. This methodology employs CS2 and amines as readily available precursors to construct dithiocarbamate structures, creating an efficient electrochemical platform for synthesizing diverse dithiocarbamate-functionalized N-heterocycles. The metal- and oxidant-free process facilitates sequential N-C and N-S bond formation, delivering target products in high yields. Significantly, the transformation exhibits remarkable regioselectivity, favoring exclusive N-S bond formation at the indole nitrogen atom while suppressing competing C-S bond generation at the C3 position. Mechanistic investigations involving controlled experiments and radical trapping studies indicate that the reaction proceeds via a radical-mediated pathway.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"127 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-10-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145305369","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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 Assembly of Dihydrofluoren-3-ones via Intramolecular Annulation of Alkynyl-Alkynones: A Way to Functionalized Fluorenes. 分子内环化二氢芴-3-酮的一锅组装：一种功能化芴的方法。
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-10-17 DOI: 10.1021/acs.joc.5c01964
Chada Raji Reddy,Ankita Kumari,Adla Vijender,Shiva Kumar Kota Balaji,René Grée
{"title":"One-Pot Assembly of Dihydrofluoren-3-ones via Intramolecular Annulation of Alkynyl-Alkynones: A Way to Functionalized Fluorenes.","authors":"Chada Raji Reddy,Ankita Kumari,Adla Vijender,Shiva Kumar Kota Balaji,René Grée","doi":"10.1021/acs.joc.5c01964","DOIUrl":"https://doi.org/10.1021/acs.joc.5c01964","url":null,"abstract":"Herein, we reveal an approach for the synthesis of a unique structural framework, dihydrofluoren-3-one, from the reaction of propargylic alcohol with alkynyl silyl enol ether. The transformation proceeds through acid-catalyzed propargylation of silyl enol ether leading to alkynyl-alkynones and subsequent intramolecular annulation (3+2 cycloaddition) in the presence of PPh3AuNTf2 (2 mol %). This novel dihydrofluoren-3-one motif was found to be a versatile precursor to provide diverse functionalized fluorenes.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"41 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-10-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145311672","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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 Isoquinoline/Quinoline/Carboline-Substituted Methylamine Derivatives by an Interrupted Ugi Three-Component Reaction. 中断Ugi三组分反应合成异喹啉/喹啉/羰基取代甲胺衍生物
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-10-17 DOI: 10.1021/acs.joc.5c01763
Lei Wang,Yangkai Wang,Xianxiu Xu,Guodong Wang,Shaoguang Sun,Mengying Jia
{"title":"Synthesis of Isoquinoline/Quinoline/Carboline-Substituted Methylamine Derivatives by an Interrupted Ugi Three-Component Reaction.","authors":"Lei Wang,Yangkai Wang,Xianxiu Xu,Guodong Wang,Shaoguang Sun,Mengying Jia","doi":"10.1021/acs.joc.5c01763","DOIUrl":"https://doi.org/10.1021/acs.joc.5c01763","url":null,"abstract":"A hexafluoroisopropanol (HFIP)-promoted Ugi three-component reaction of electron rich aryl, alkenyl or heteroaryl group-tethered isocyanides, aldehydes and amines was developed for the rapid and general synthesis of a wide range of isoquino-line/quinoline/carboline-substituted methylamine and α-amino acid derivatives. In this reaction, the in situ formed nitrilium was intramolecularly trapped by the nucleophiles tethered at isocyanides to form the corresponding heterocyclic framework, wherein an obviously gem-disubstituent (Thorpe-Ingold) effect was observed.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"35 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-10-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145311674","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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
How to Form Two Bonds in Three Ways: Reaction Trinity of σ,π-Heterosymmetric Diradicals. 如何以三种方式形成双键：σ、π-异对称双基的反应三位一体。
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-10-16 DOI: 10.1021/acs.joc.5c01539
Haonan Cheng,Yun Zeng,Xiaofan Zhang,Fangxu Pu,Aiguo Hu,Yun Ding
{"title":"How to Form Two Bonds in Three Ways: Reaction Trinity of σ,π-Heterosymmetric Diradicals.","authors":"Haonan Cheng,Yun Zeng,Xiaofan Zhang,Fangxu Pu,Aiguo Hu,Yun Ding","doi":"10.1021/acs.joc.5c01539","DOIUrl":"https://doi.org/10.1021/acs.joc.5c01539","url":null,"abstract":"σ,π-Heterosymmetric diradicals are typically formed through the Myers-Saito cyclization of enyne-allene, featuring distinct chemical environments for the two radicals. In this study, maleic hydrazide was introduced at the ene position of enediyne molecules, leveraging the electron-withdrawing properties of these groups to facilitate the rearrangement of enediyne into enyne-allene, which subsequently leads to the generation of σ,π-heterosymmetric diradicals through cycloaromatization. Based on experimental results and computational analysis, we identified three competing reaction pathways for σ,π-heterosymmetric diradicals: (1) hydrogen atom abstraction by diradicals, (2) interactions of π-radicals with nucleophiles, and (3) interactions of σ-radicals with nucleophiles. In path 1, both radical centers can readily abstract hydrogens, with the σ-radical, showing a clear preference. In paths 2 and 3, the distortion of the core aromatic ring during the nucleophilic reaction leads to the disruption of the orthogonality of the radical orbitals through the formation of a Möbius-like conjugated framework, providing an efficient pathway for electron transfer and thereby facilitating both diradical quenching and nucleophilic addition.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"65 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-10-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145305428","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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 Oxidative Coupling of 2-Naphthols Catalyzed by Chiral Copper–Amino Acid-Derived Ligand Complexes 手性铜-氨基酸配体络合物催化2-萘酚的不对称氧化偶联
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-10-16 DOI: 10.1021/acs.joc.5c01655
Pei Tian, Mukeremu Aibibula, Xiangyu Sun, Yujie Wang, Tongtong Liu, Wenxuan Yu, Xiaohui Zhang, Xiaoyu Dong, Yan Xiong
{"title":"Asymmetric Oxidative Coupling of 2-Naphthols Catalyzed by Chiral Copper–Amino Acid-Derived Ligand Complexes","authors":"Pei Tian, Mukeremu Aibibula, Xiangyu Sun, Yujie Wang, Tongtong Liu, Wenxuan Yu, Xiaohui Zhang, Xiaoyu Dong, Yan Xiong","doi":"10.1021/acs.joc.5c01655","DOIUrl":"https://doi.org/10.1021/acs.joc.5c01655","url":null,"abstract":"We developed a [Cu(CH<sub>3</sub>CN)<sub>4</sub>]<sup>+</sup>BF<sub>4</sub><sup>–</sup>/air-mediated asymmetric coupling method using novel <span>l</span>-amino acid-derived aminopyridine–amide ligands to access various <i>C</i><sub>2</sub>/<i>C</i><sub>1</sub>-symmetric BINOLs. This represents the first application of amide-containing ligands in copper-catalyzed asymmetric oxidative coupling of 2-naphthols. Notably, the efficient one-pot integration of the transesterification and coupling processes establishes a novel strategy for synthesizing ester-functionalized BINOLs. The formation of highly active Cu<sub>2</sub>O<sub>3</sub> oxides was detected from Cu(I) species under single-crystal X-ray diffraction analysis and is the key determinant for the stereoselective control of the catalytic cycle. Moreover, this method also enables the efficient synthesis of racemic binaphtholone compounds.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"92 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-10-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145296014","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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 Ni-Catalyzed Selective Mono-N-Arylation 光化学镍催化选择性单- n -芳基化
IF 4.354 2区 化学
Journal of Organic Chemistry Pub Date : 2025-10-16 DOI: 10.1021/acs.joc.5c02127
Geyang Song, Ding-Zhan Nong, Gang Li, Juan Fan, Dong Xue
{"title":"Photochemical Ni-Catalyzed Selective Mono-N-Arylation","authors":"Geyang Song, Ding-Zhan Nong, Gang Li, Juan Fan, Dong Xue","doi":"10.1021/acs.joc.5c02127","DOIUrl":"https://doi.org/10.1021/acs.joc.5c02127","url":null,"abstract":"The selective synthesis of <i>N</i>-monomethyl arylamines presents an important challenge in synthetic chemistry. Furthermore, small molecule amines readily coordinate with metal catalysts, causing catalyst deactivation. In this work, we report an efficient C–N coupling reaction of (hetero)aryl halides with small molecule amine salts. Without the need for an external photosensitizer in the presence of a soluble organic base, a bipyridine-Ni(II) complex serving as a catalyst successfully enables the selective C–N coupling of (hetero)aryl halides with methylamine, deuterated methylamine, ethylamine, and dimethylamine under purple light irradiation (390–395 nm), thus preventing catalyst deactivation. Mechanistic studies reveal that the reaction proceeds via a Ni(I)–Ni(III) catalytic cycle, and more than 100 examples showcase its feasibility and versatility in organic synthesis.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"77 1","pages":""},"PeriodicalIF":4.354,"publicationDate":"2025-10-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145306324","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"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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