Asian Journal of Organic Chemistry最新文献_第8页

Zinc‐Mediated C–H Borylation of Terminal Alkynes: Mechanistic Insights 锌介导的末端炔的C-H硼化反应：机理研究

IF 2.7 4区化学

Asian Journal of Organic Chemistry Pub Date : 2026-03-01 Epub Date: 2026-03-28 DOI: 10.1002/ajoc.202500637

Nithya M. Thilakan , Sagrika Rajput , Sayantan Mukhopadhyay , Sharanappa Nembenna

{"title":"Zinc‐Mediated C–H Borylation of Terminal Alkynes: Mechanistic Insights","authors":"Nithya M. Thilakan , Sagrika Rajput , Sayantan Mukhopadhyay , Sharanappa Nembenna","doi":"10.1002/ajoc.202500637","DOIUrl":"10.1002/ajoc.202500637","url":null,"abstract":"<div><div>A three‐coordinate amido zinc (II) complex, [L1ZnN(SiMe3)2] (Zn‐1), supported by a bis‐guanidinate ligand {L1 = (ArHN)(ArN)─C═N─C═(NAr)(NHAr); Ar = 2,6‐Et2C6H3}, has been synthesized and structurally characterized, via NMR, high‐resolution mass spectrometry, and single‐crystal x‐ray diffraction analyses. Zn‐1 acts as an efficient pre‐catalyst for the C–H borylation of terminal alkynes, affording the corresponding alkynyl boronates in excellent yields. Comparative studies with a β‐diketiminate‐supported analogue [L2ZnN(SiMe3)2] (Zn‐1′; L2 = [CH‐{(CMe)(NAr)}2]; Ar = 2,6‐Et2‐C6H3) revealed comparable catalytic activity, with Zn‐1 showing slightly higher conversion. The catalytically relevant new bis‐guanidinate zinc acetylide intermediate [L1Zn–C≡C–(4‐OMe–C6H4)]2(Zn‐2) was isolated and fully characterized. Stoichiometric investigations support a plausible catalytic cycle. This study highlights the key role of bis‐guanidinate ligation in enhancing zinc‐mediated alkyne borylation reactivity.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"15 3","pages":"Article e00637"},"PeriodicalIF":2.7,"publicationDate":"2026-03-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"147563232","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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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Unlocking Potent Anti‐Breast Cancer Imidazoles: A Streamlined Synthesis and In‐Depth Theoretical Insights 解锁有效的抗乳腺癌咪唑：流线型合成和深入的理论见解

IF 2.7 4区化学

Asian Journal of Organic Chemistry Pub Date : 2026-03-01 Epub Date: 2026-03-28 DOI: 10.1002/ajoc.70379

Ankur Basak , Nirbhik Chatterjee , Tanmoy Dutta , Krishna Chattopadhyay , Saikat Khamarui , Dilip K. Maiti

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Transition‐Metal‐Free LiOtBu‐Promoted Three‐Component Reaction for Efficient Synthesis of Triazolyl (Thio)ureas 过渡金属-无LiOtBu -促进三组分反应高效合成三唑基（硫）脲

IF 2.7 4区化学

Asian Journal of Organic Chemistry Pub Date : 2026-03-01 Epub Date: 2026-03-28 DOI: 10.1002/ajoc.70375

Weiguo Wang , Chunpeng Qiu , Zhihao Zuo , Younan Wang , Jingyu Wang

{"title":"Transition‐Metal‐Free LiOtBu‐Promoted Three‐Component Reaction for Efficient Synthesis of Triazolyl (Thio)ureas","authors":"Weiguo Wang , Chunpeng Qiu , Zhihao Zuo , Younan Wang , Jingyu Wang","doi":"10.1002/ajoc.70375","DOIUrl":"10.1002/ajoc.70375","url":null,"abstract":"<div><div>A transition‐metal‐free LiOtBu‐promoted three‐component reaction for efficient synthesis of the triazolyl (thio)ureas has been reported. This reaction proceeded via the cyclocondensation of nitriles and azides in the presence of a base, followed by the interception of the triazolamine and triazole nitrogen anion intermediate using (thio)carbamoylimidazoles. This method is characterized by being transition‐metal‐free, a broad substrate scope, and mild reaction conditions.</div></div><div>A transition‐metal‐free LiOtBu‐promoted three‐component reaction for efficient synthesis of the triazolyl (thio)ureas has been reported. This reaction proceeded via the cyclocondensation of nitriles and azides in the presence of a base, followed by the interception of the triazolamine and triazole nitrogen anion intermediate using (thio)carbamoylimidazoles. This method is characterized by being transition‐metal‐free, a broad substrate scope, and mild reaction conditions.</div><div>A transition‐metal‐free LiOtBu‐promoted three‐component reaction has been developed for synthesis of triazolyl (thio)ureas under mild reaction conditions.\u0000<figure><img><ol><li>Download: Download high-res image (8KB)</li><li>Download: Download full-size image</li></ol></figure></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"15 3","pages":"Article e70375"},"PeriodicalIF":2.7,"publicationDate":"2026-03-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"147612057","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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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Magnesium Triflimide‐Catalyzed Chemoselective Diacetylation of Aldehydes 三氟氰镁催化醛的化学选择性二乙酰化

IF 2.7 4区化学

Asian Journal of Organic Chemistry Pub Date : 2026-03-01 Epub Date: 2026-03-28 DOI: 10.1002/ajoc.70374

Shujie Li , Yiting Xiong , Mengyun Chen , Junshuo Chen , Juan Tian , Dayong Sang , Ying Peng

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Construction of Trideuteromethyl‐Aryl Ethers via the Pd(II)‐Catalyzed Trideuteromethoxylation of Ortho C(sp2)‐H Bonds of Aromatic Rings Pd（II）催化芳香环邻位C(sp2)-H键三氘甲氧基化构建三氘甲基芳基醚

IF 2.7 4区化学

Asian Journal of Organic Chemistry Pub Date : 2026-03-01 Epub Date: 2026-03-28 DOI: 10.1002/ajoc.70338

Yashika Aggarwal , Srinivasarao Arulananda Babu , Pooja Patel

{"title":"Construction of Trideuteromethyl‐Aryl Ethers via the Pd(II)‐Catalyzed Trideuteromethoxylation of Ortho C(sp2)‐H Bonds of Aromatic Rings","authors":"Yashika Aggarwal , Srinivasarao Arulananda Babu , Pooja Patel","doi":"10.1002/ajoc.70338","DOIUrl":"10.1002/ajoc.70338","url":null,"abstract":"<div><div>This paper reports the utility of Pd(II)‐catalyzed bidentate directing group picolinamide‐aided (ortho) γ‐ or δ‐C‐H oxygenation and trideuteromethoxylation of aromatic rings, as a route for constructing new entities of trideuteromethyl‐aryl ethers. Accordingly, the introduction of the O‐CD3 unit in the ortho position of aromatic rings in α‐alkylbenzylamines, amino alcohols, and amino acids with CD3OD or CD3CD2OD was accomplished. Apart from the picolinamide directing group, other directing groups, such as 5‐methylisoxazole‐3‐carboxamide (MICA), quinoline‐2‐carboxamide, and benzamide directing groups, were used for conducting the trideuteromethoxylation of aromatic rings of the target compound, and the picolinamide DG was found to be efficient in all reactions. We have described the synthetic utility of the trideuteromethoxylated aryl ethers obtained in this work by synthesizing aromatic motif‐based peptides using deuteromethoxylated compounds and trideuteromethoxylated α‐methylbenzylamine‐derived sulfamoylcarbamate motifs. Various deuterium‐containing compounds, particularly aromatic rings containing N‐CD3 or O‐CD3 units, are known as potential drug candidates in the literature. Accordingly, this work contributes to enriching the library of O‐CD3 or O‐CD2CD3 unit‐containing aromatic motifs and a method for their preparation through directing group‐aided trideuteromethoxylation or pentadeuteroethoxylation of ortho C(sp2)─H bonds of aromatic rings.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"15 3","pages":"Article e70338"},"PeriodicalIF":2.7,"publicationDate":"2026-03-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"147563273","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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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Potassium‐Sodium Co‐ doped Carbon Nitride for Enhanced Visible‐Light‐Driven Heterogeneous Photocatalytic Hydroalkylation of Arylazo tert‐Butyl Carboxylates 钾钠掺杂氮化碳增强可见光驱动非均相光催化芳基叔丁基羧酸氢烷基化

IF 2.7 4区化学

Asian Journal of Organic Chemistry Pub Date : 2026-03-01 Epub Date: 2026-03-28 DOI: 10.1002/ajoc.70348

Wenjie Zhang , Zezhao Huang , Zeyao Liang , Sen Xu , Li Zhu , Xiaoquan Yao

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Ruthenium Supported Ionic Liquid Based PMO as an Efficient Heterogeneous Catalyst for sp3 C─H Bond Alkylation of 9H‐Fluorene With Primary Alcohols 钌负载离子液体PMO作为9h -芴与伯醇sp3 C─H键烷基化的高效非均相催化剂

IF 2.7 4区化学

Asian Journal of Organic Chemistry Pub Date : 2026-03-01 Epub Date: 2026-03-28 DOI: 10.1002/ajoc.70342

Amit. B. Soni , G. Satishkumar

{"title":"Ruthenium Supported Ionic Liquid Based PMO as an Efficient Heterogeneous Catalyst for sp3 C─H Bond Alkylation of 9H‐Fluorene With Primary Alcohols","authors":"Amit. B. Soni , G. Satishkumar","doi":"10.1002/ajoc.70342","DOIUrl":"10.1002/ajoc.70342","url":null,"abstract":"<div><div>Substituted monoalkylated fluorene derivatives are mainly found in pharmaceuticals, polymerization synthesis, plastics, and dye industries. Therefore, synthesis of monoalkylated fluorene derivatives is highly significant and desirable. In this work, periodic mesoporous organo‐silica(PMO) has been functionalized by ionic liquid 1‐methyl‐3‐(trimethoxysilylpropyl) imidazolium chloride by utilizing the alkoxy groups (‐OR) located in the pore wall of PMO, which assists in the effective stabilization of Ru supported over PMO‐IL. The textural, structural, and morphological properties of the catalyst was studied by various analytical techniques such as XRD, BET, TGA, FTIR, 29Si(CP‐MAS), 13C(CP‐MAS)‐NMR, XPS, ICP‐OES, FE‐SEM, and HR‐TEM. In this study, we present a green and efficient protocol for the synthesis of monoalkylated derivatives via sp3 C‐H bond functionalization of 9H‐fluorene with primary alcohol by adopting the borrowing hydrogen strategy, thereby excluding the use of toxic alkyl halides. The reaction was catalyzed by minimal loading of Ru@PMO‐IL (2.5 wt%), without the requirement of any ligands and external hydrogen source. The resulting catalyst showed excellent catalytic activity, high turnover number (TON), along with a wide range of substrate scope, which includes substituted primary alcohols and substituted 9H‐fluorene derivatives, affording the corresponding alkylated products in good to excellent yields. Further, the catalyst was recycled for five catalytic cycles and showed insignificant loss in catalytic activity.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"15 3","pages":"Article e70342"},"PeriodicalIF":2.7,"publicationDate":"2026-03-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"147563723","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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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A Rotaxane Strategy to Improve the Photosensitizing and Photodurable Abilities Upon a Bis(bromophenyl)Acetylene Dye 一种提高双（溴苯）乙炔染料光敏性和光耐久性的轮烷策略

IF 2.7 4区化学

Asian Journal of Organic Chemistry Pub Date : 2026-03-01 Epub Date: 2026-03-28 DOI: 10.1002/ajoc.70349

Taiki Ichikawa , Keita Serizawa , Yuki Ohishi , Junya Chiba , Masahiko Inouye

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Design, Synthesis, and Pb2+‐Selective Optical Sensing Properties of Novel π‐Conjugated Dibenzosuberenone–Dihydropyridazine Fluorophores 新型π共轭二苯并醌-二氢吡啶类荧光团的设计、合成及Pb2+选择性光学传感性能

IF 2.7 4区化学

Asian Journal of Organic Chemistry Pub Date : 2026-03-01 Epub Date: 2026-03-28 DOI: 10.1002/ajoc.70359

Khadijeh Ganjehyan , Esra Sahin , Recep Isci , Arif Daştan , Musa Erdoğan

{"title":"Design, Synthesis, and Pb2+‐Selective Optical Sensing Properties of Novel π‐Conjugated Dibenzosuberenone–Dihydropyridazine Fluorophores","authors":"Khadijeh Ganjehyan , Esra Sahin , Recep Isci , Arif Daştan , Musa Erdoğan","doi":"10.1002/ajoc.70359","DOIUrl":"10.1002/ajoc.70359","url":null,"abstract":"<div><div>Herein, five new π‐conjugated small organic molecules (DD1‐DD5) were synthesized starting from dibenzosuberone (1), applying a modular approach based on Suzuki coupling and Diels–Alder/retro‐Diels–Alder (DA/rDA) reactions. The key intermediate, dibromodibenzosuberenone 4, was obtained in three steps, and its Suzuki couplings with aryl and heteroaryl boronic acids furnished compounds 10‐12. A Sonogashira‐type modification of compound 4 enabled the preparation of the diacetylene derivative 14, which, together with compounds 10‐12, was reacted with tetrazines 20 and 22 via DA/rDA reactions to afford the target cycloadducts DD1‐DD5. All compounds were characterized by NMR, FT‐IR, and HRMS analyses. UV–vis and fluorescence studies demonstrated that all DD1‐DD5 derivatives exhibited pronounced selectivity and high sensitivity toward Pb2+ ions, showing distinct absorbance changes, strong turn‐on emission, and >100 nm mega‐Stokes shifts. DD1 displayed the most significant Pb2+ response, while electron‐withdrawing groups of DD4 (–NO2) and DD5 (–CF3) modulated their optical behavior. Additional but weaker selectivity toward Fe3+ was observed for DD4 and DD5. Job plot analysis indicated 1:1 binding for DD1‐DD2 and 2:1 Pb2+–ligand stoichiometry for DD3‐DD5. 1H NMR titrations supported Pb2+ complexation and revealed multi‐dentate binding, particularly for DD3. Overall, the DD scaffold provides a tunable platform for selective Pb2+ sensing with complementary anion‐responsive behavior.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"15 3","pages":"Article e70359"},"PeriodicalIF":2.7,"publicationDate":"2026-03-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"147563238","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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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Influence of Phenyl Substitution Position on the Physical Properties of Diazachrysenes 苯基取代位置对二氮杂蒽物理性质的影响

IF 2.7 4区化学

Asian Journal of Organic Chemistry Pub Date : 2026-03-01 Epub Date: 2026-03-28 DOI: 10.1002/ajoc.70356

Yuanrong Shan , Hidetoyo Kanzawa , Jinxian Huang , Takeshi Yasuda , Yukihiro Shimoi , Kazuhiro Marumoto , Takaki Kanbara , Junpei Kuwabara

{"title":"Influence of Phenyl Substitution Position on the Physical Properties of Diazachrysenes","authors":"Yuanrong Shan , Hidetoyo Kanzawa , Jinxian Huang , Takeshi Yasuda , Yukihiro Shimoi , Kazuhiro Marumoto , Takaki Kanbara , Junpei Kuwabara","doi":"10.1002/ajoc.70356","DOIUrl":"10.1002/ajoc.70356","url":null,"abstract":"<div><div>Aryl‐substituted 4,10‐diazachrysenes were synthesized to investigate the influence of substitution positions on their fundamental physical properties. A crystallographic analysis revealed that 3,9‐diphenyl diazachrysene (3,9‐DiPh) adopts a planar geometry, whereas 5,11‐diphenyl derivative (5,11‐DiPh) exhibits a distorted framework because of steric repulsion between the phenyl groups and diazachrysene core. Photophysical studies have shown that 3,9‐DiPh exhibits red‐shifted photoluminescence compared to the parent diazachrysene, whereas 5,11‐DiPh is non‐emissive. Furthermore, introducing substituents such as –nBu, and –F on the phenyl rings at the 3 and 9 positions slightly modulated the absorption and emission profiles depending on the electronic nature of the substituents. These findings provide fundamental insights into the structure–property relationships of diazachrysene derivatives and offer guidance for future molecular design.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"15 3","pages":"Article e70356"},"PeriodicalIF":2.7,"publicationDate":"2026-03-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"147563898","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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