Asian Journal of Organic Chemistry最新文献_第5页

Rh-Catalyzed [4+2+1] Cycloaddition Reactions of Ene-Allenes with Alkynes/Allenes/Alkenes and CO 铑催化烯-烯与炔/烯/烯和一氧化碳的[4+2+1]环加成反应

IF 2.7 4区化学

Asian Journal of Organic Chemistry Pub Date : 2026-03-07 DOI: 10.1002/ajoc.70295

Liang Dang, Ling-Ling Ma, Zhi-Xiang Yu

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Rh-Catalyzed [4+2+1] Cycloaddition Reactions of Ene-Allenes with Alkynes/Allenes/Alkenes and CO 铑催化烯-烯与炔/烯/烯和一氧化碳的[4+2+1]环加成反应

IF 2.7 4区化学

Asian Journal of Organic Chemistry Pub Date : 2026-03-07 DOI: 10.1002/ajoc.70295

Liang Dang, Ling-Ling Ma, Zhi-Xiang Yu

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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 : 2026-03-07 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>\u0000 \u0000 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.\u0000 </div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"15 3","pages":""},"PeriodicalIF":2.7,"publicationDate":"2026-03-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"147563720","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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Visible-Light Mediated One-Pot Synthesis of Pyrazolo[3,4-b]Pyridines via Intramolecular Rearrangement 可见光介导的分子内重排法合成吡唑[3,4-b]吡啶

IF 2.7 4区化学

Asian Journal of Organic Chemistry Pub Date : 2026-03-06 DOI: 10.1002/ajoc.70344

Swetha Singitham, Mary Sravani Galla, Subha Jahnavi Avvaru, Manda Sathish, Pooja Kumari, Amol G. Dikundwar, Nagula Shankaraiah

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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 : 2026-03-06 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>\u0000 \u0000 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.\u0000 </div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"15 3","pages":""},"PeriodicalIF":2.7,"publicationDate":"2026-03-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"147563680","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

Visible-Light Mediated One-Pot Synthesis of Pyrazolo[3,4-b]Pyridines via Intramolecular Rearrangement 可见光介导的分子内重排法合成吡唑[3,4-b]吡啶

IF 2.7 4区化学

Asian Journal of Organic Chemistry Pub Date : 2026-03-06 DOI: 10.1002/ajoc.70344

Swetha Singitham, Mary Sravani Galla, Subha Jahnavi Avvaru, Manda Sathish, Pooja Kumari, Amol G. Dikundwar, Nagula Shankaraiah

引用次数: 0

Mechanochemical Ester Activation With La(III): Efficient Amidation Under Mild and Moisture-Tolerant Conditions La（III）的机械化学酯活化：在温和和耐湿条件下的高效酰胺化

IF 2.7 4区化学

Asian Journal of Organic Chemistry Pub Date : 2026-03-04 DOI: 10.1002/ajoc.70300

Cheng-Hsu Li, Yi-Jin You, Jian-Ming Wong, Hsiao-Yin Hou, Sung-Han Chen, Palanivelmurugan Mohanasundaram, Jia-Han Jiang, Cheng-I Lee, Ching-Chieh Weng, Pei-Jhen Li

{"title":"Mechanochemical Ester Activation With La(III): Efficient Amidation Under Mild and Moisture-Tolerant Conditions","authors":"Cheng-Hsu Li, Yi-Jin You, Jian-Ming Wong, Hsiao-Yin Hou, Sung-Han Chen, Palanivelmurugan Mohanasundaram, Jia-Han Jiang, Cheng-I Lee, Ching-Chieh Weng, Pei-Jhen Li","doi":"10.1002/ajoc.70300","DOIUrl":"https://doi.org/10.1002/ajoc.70300","url":null,"abstract":"<div>\u0000 \u0000 Amide bonds are fundamental linkages in biomolecules and pharmaceuticals, yet their construction often relies on stoichiometric coupling reagents and high-energy input. Here, we report a mechanistically distinctive ester-to-amide conversion that integrates solvent-minimized ball milling with either metal-free conditions or lanthanide promotion, achieving efficient amidation under mild and scalable conditions. The method employs methyl and 2-picolyl (Pic) esters as acyl donors and proceeds rapidly with both primary and secondary amines without solvent pre-drying or inert handling. The 2-picolyl group facilitates acyl activation through La3+ coordination with the carbonyl oxygen and pyridyl nitrogen, while the stability of 2-picolyl alcohol drives amide formation. Electronic substituents at the α-position modulate the preference between metal-promoted and nonmetallic pathways. Incorporation of electron-withdrawing groups such as fluorine or cyano further expands reactivity. The reaction operates efficiently under both ball-milling and aqueous conditions, with gram-scale amidations confirming practicality. Representative examples include pharmaceutically relevant compounds, glycan derivatives, amino acids, and fluorescent probes, as well as biomacromolecular functionalization. This work establishes a novel and mechanistically defined platform for sustainable amide bond formation, bridging mechanochemistry and solution-phase reactivity.\u0000 </div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"15 3","pages":""},"PeriodicalIF":2.7,"publicationDate":"2026-03-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"147563233","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

Mechanochemical Ester Activation With La(III): Efficient Amidation Under Mild and Moisture-Tolerant Conditions La（III）的机械化学酯活化：在温和和耐湿条件下的高效酰胺化

IF 2.7 4区化学

Asian Journal of Organic Chemistry Pub Date : 2026-03-04 DOI: 10.1002/ajoc.70300

Cheng-Hsu Li, Yi-Jin You, Jian-Ming Wong, Hsiao-Yin Hou, Sung-Han Chen, Palanivelmurugan Mohanasundaram, Jia-Han Jiang, Cheng-I Lee, Ching-Chieh Weng, Pei-Jhen Li

{"title":"Mechanochemical Ester Activation With La(III): Efficient Amidation Under Mild and Moisture-Tolerant Conditions","authors":"Cheng-Hsu Li, Yi-Jin You, Jian-Ming Wong, Hsiao-Yin Hou, Sung-Han Chen, Palanivelmurugan Mohanasundaram, Jia-Han Jiang, Cheng-I Lee, Ching-Chieh Weng, Pei-Jhen Li","doi":"10.1002/ajoc.70300","DOIUrl":"10.1002/ajoc.70300","url":null,"abstract":"<div>\u0000 \u0000 Amide bonds are fundamental linkages in biomolecules and pharmaceuticals, yet their construction often relies on stoichiometric coupling reagents and high-energy input. Here, we report a mechanistically distinctive ester-to-amide conversion that integrates solvent-minimized ball milling with either metal-free conditions or lanthanide promotion, achieving efficient amidation under mild and scalable conditions. The method employs methyl and 2-picolyl (Pic) esters as acyl donors and proceeds rapidly with both primary and secondary amines without solvent pre-drying or inert handling. The 2-picolyl group facilitates acyl activation through La3+ coordination with the carbonyl oxygen and pyridyl nitrogen, while the stability of 2-picolyl alcohol drives amide formation. Electronic substituents at the α-position modulate the preference between metal-promoted and nonmetallic pathways. Incorporation of electron-withdrawing groups such as fluorine or cyano further expands reactivity. The reaction operates efficiently under both ball-milling and aqueous conditions, with gram-scale amidations confirming practicality. Representative examples include pharmaceutically relevant compounds, glycan derivatives, amino acids, and fluorescent probes, as well as biomacromolecular functionalization. This work establishes a novel and mechanistically defined platform for sustainable amide bond formation, bridging mechanochemistry and solution-phase reactivity.\u0000 </div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"15 3","pages":""},"PeriodicalIF":2.7,"publicationDate":"2026-03-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"147562962","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

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 : 2026-03-04 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>\u0000 \u0000 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.\u0000 </div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"15 3","pages":""},"PeriodicalIF":2.7,"publicationDate":"2026-03-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"147563128","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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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 : 2026-03-04 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>\u0000 \u0000 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.\u0000 </div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"15 3","pages":""},"PeriodicalIF":2.7,"publicationDate":"2026-03-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"147563271","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