Asian Journal of Organic Chemistry最新文献_第3页

Self‐Assembly and Emission Properties of Benzo[e]pyrene Dicarboxylic Acid in Solution and Solid States 苯并[e]芘二羧酸在溶液和固体状态下的自组装和发射性质

IF 2.7 4区化学

Asian Journal of Organic Chemistry Pub Date : 2025-10-01 DOI: 10.1002/ajoc.202500544

Svetlana Em , Katsuaki Iwasa , Mikey Nishimoto , Yumi Yakiyama , Hidehiro Sakurai

{"title":"Self‐Assembly and Emission Properties of Benzo[e]pyrene Dicarboxylic Acid in Solution and Solid States","authors":"Svetlana Em , Katsuaki Iwasa , Mikey Nishimoto , Yumi Yakiyama , Hidehiro Sakurai","doi":"10.1002/ajoc.202500544","DOIUrl":"10.1002/ajoc.202500544","url":null,"abstract":"<div><div>A new pyrene derivative, <strong>1</strong>, containing a benzene dicarboxylic acid moiety at the K‐region of pyrene was studied to explore its potential for producing highly sensitive self‐assembled structures in both solid and solution states. Single crystal X‐ray analysis revealed that <strong>1</strong> shows crystal polymorphism, producing two distinct structures: a non‐solvated form (crystal A) and a solvent‐incorporated form (crystal B). The effects of the external environment on the self‐assembly process, as well as the optical properties of the compound in solid and solution states were investigated. Solid‐state emission spectroscopy revealed excimer emission from the pyrene units in both crystals, consistent with the observed packing structures. In the case of the solution, three key factors were identified to affect the photophysical behavior: 1) concentration, 2) hydrogen‐bonding, and 3) pH. A clear bathochromic shift was observed under acidic conditions, attributed to changes in protonation states and stacking modes between acidic and basic environments.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 10","pages":"Article e00544"},"PeriodicalIF":2.7,"publicationDate":"2025-10-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145317711","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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Progress in Strain Promoted Azide‐Alkyne Cycloaddition (SPAAC) Reaction and Their Applications 应变促进叠氮-炔环加成（SPAAC）反应及其应用研究进展

IF 2.7 4区化学

Asian Journal of Organic Chemistry Pub Date : 2025-10-01 DOI: 10.1002/ajoc.202500505

Ranjana Upadhyay , Satvik Rastogi , Akash K. Mishra , Shruti Yadav , Dr. Anuj K. Yadav , Dr. Sushil K. Maurya

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Advanced Pd–NAPA Precatalysts for Broad‐Scope Kumada–Tamao–Corriu Couplings of Challenging Aryl Chlorides 先进的Pd-NAPA预催化剂用于挑战性芳氯化物的大范围Kumada-Tamao-Corriu偶联

IF 2.7 4区化学

Asian Journal of Organic Chemistry Pub Date : 2025-10-01 DOI: 10.1002/ajoc.202500332

Pei‐Zhen Xie , Wan‐Qin Zeng , Yu‐Hsiang Liu , Yingjie Guo , Hsuan‐Hao Kang , Yung‐De Tsai , Yi‐Jie Tsai , Li‐Hui Hong , Yun‐Rou Zeng , Yen‐Hsien Li , Wei‐Chih Chen , I‐Chung Lu , Yu‐Chang Chang

{"title":"Advanced Pd–NAPA Precatalysts for Broad‐Scope Kumada–Tamao–Corriu Couplings of Challenging Aryl Chlorides","authors":"Pei‐Zhen Xie , Wan‐Qin Zeng , Yu‐Hsiang Liu , Yingjie Guo , Hsuan‐Hao Kang , Yung‐De Tsai , Yi‐Jie Tsai , Li‐Hui Hong , Yun‐Rou Zeng , Yen‐Hsien Li , Wei‐Chih Chen , I‐Chung Lu , Yu‐Chang Chang","doi":"10.1002/ajoc.202500332","DOIUrl":"10.1002/ajoc.202500332","url":null,"abstract":"<div><div>A series of NHC and phosphinous acid‐based palladium precatalysts (NAPA), (i.e., <strong>1b</strong>–<strong>1d</strong>: SIPr‐PdCl<sub>2</sub>‐PAr<sub>2</sub>(OH)), and their efficiency in catalyzing Kumada–Tamao−Corriu (KTC) couplings are reported. The <strong>1</strong>‐catalyzed KTC couplings could reach high yields at 50 °C in 3 h. Good results were obtained for strained tetra‐ortho‐substituted biaryl products by raising the temperature to 80 °C and reacting for 3 h. Functional‐group tolerance was achieved using dropwise addition of Grignard reagent during the reaction time course. Upon deprotonation of the ligated PAr<sub>2</sub>(OH), density functional theory (DFT) calculations and negative‐ion mode electrospray mass spectrometer (ESI‐MS) revealed that SIPr tended to dissociate from the Pd(II), implying the succeeding generation of Pd(0)‐P(O<sup>−</sup>)Ar<sub>2</sub> active species. Compared to Pd(0)‐SPhos and Pd(0)‐NHC, the oxidative addition of 4‐chlorobenzonitrile to Pd(0) was computed, showing the Pd(0)–P(O<sup>−</sup>)Ar<sub>2</sub> has the lowest activation free energy.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 10","pages":"Article e00332"},"PeriodicalIF":2.7,"publicationDate":"2025-10-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145317555","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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Terphenyl‐Derived Covalent Organic Polymer as Metal‐Free Catalyst for the Cycloaddition Reaction of Carbon Dioxide with Spiro‐Epoxy Oxindoles 三苯基衍生共价有机聚合物作为无金属催化剂用于二氧化碳与螺型环氧氧吲哚的环加成反应

IF 2.7 4区化学

Asian Journal of Organic Chemistry Pub Date : 2025-10-01 DOI: 10.1002/ajoc.202500570

Shilpa Dabas , Prabhahar Murugan , Brijesh Patel , Mahanthi Lingaraju , Saravanan Subramanian

{"title":"Terphenyl‐Derived Covalent Organic Polymer as Metal‐Free Catalyst for the Cycloaddition Reaction of Carbon Dioxide with Spiro‐Epoxy Oxindoles","authors":"Shilpa Dabas , Prabhahar Murugan , Brijesh Patel , Mahanthi Lingaraju , Saravanan Subramanian","doi":"10.1002/ajoc.202500570","DOIUrl":"10.1002/ajoc.202500570","url":null,"abstract":"<div><div>Covalent organic polymers are a class of fascinating material derived from pre‐designed molecular scaffolds with tailorable structural features. The choice of designed functionalities and prospective strategy for its preparation enables them to address the application requirements. In this work, we report the synthesis of a spherical covalent organic polymer (COP) derived from terphenyl structural unit, achieved through a template‐free condensation reaction. The prepared material demonstrated efficient organocatalytic activity toward the cycloaddition reaction of carbon dioxide with spiro‐epoxy oxindoles to access spirocyclic carbonates (63%–99%) under ambient reaction conditions. Notably, the organic material outperformed its corresponding monomeric unit, which clearly reveals the requirement of a covalent organic polymer. The heterogeneous organic material is found to be recyclable for four times with retention of its catalytic activity. The calculated green metrics reveal that the developed catalytic protocol is efficient, creates minimal waste, and is environmentally friendly.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 10","pages":"Article e00570"},"PeriodicalIF":2.7,"publicationDate":"2025-10-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145317696","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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Synthesis of Diaryl Thiosulfonates via Electrochemical Cascade S─S‐Coupling Using Arylsulfonyl Chlorides/Arylsulfinate Salts 芳基磺酰氯/芳基亚磺酸盐电化学级联S─S偶联合成二芳基硫代磺酸盐

IF 2.7 4区化学

Asian Journal of Organic Chemistry Pub Date : 2025-10-01 DOI: 10.1002/ajoc.202500499

Prof. Dr. Sushobhan Chowdhury , Madhubala , Manoj Kumar Yadav , Ajay Kumar

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The Structure of Nitro‐ and Polynitropyrazoles: X‐Ray Crystallography Versus Theoretical Calculations 硝基和多硝基吡唑的结构：x射线晶体学与理论计算

IF 2.7 4区化学

Asian Journal of Organic Chemistry Pub Date : 2025-10-01 DOI: 10.1002/ajoc.202500400

Rosa M. Claramunt , Marta Pérez‐Torralba , José Elguero , Ibon Alkorta

{"title":"The Structure of Nitro‐ and Polynitropyrazoles: X‐Ray Crystallography Versus Theoretical Calculations","authors":"Rosa M. Claramunt , Marta Pérez‐Torralba , José Elguero , Ibon Alkorta","doi":"10.1002/ajoc.202500400","DOIUrl":"10.1002/ajoc.202500400","url":null,"abstract":"<div><div>This publication presents the geometries of 157 nitro‐ and polynitropyrazoles. Among these, 109 compounds were theoretically studied using mainly the B3LYP/6–311++G(d,p) level of theory. Three‐parameter Lee‐Yang‐Parr (B3LYP) is a density functional theory (DFT) method widely used in computational chemistry and constitutes an acceptable compromise for such a large set of compounds, some of them of considerable mass. The data set includes crystallographic parameters for 91 polynitropyrazoles; the remaining 67 compounds comprise 40 known and 27 newly reported structures. Several key issues are addressed: the investigation of 3,4‐dinitro‐1<em>H</em>‐pyrazole, including nine X‐ray structures (solvates and cocrystals); the prototropic tautomerism observed in four pairs of pyrazoles and the factors influencing the preference for a tautomer; the analysis of twelve 1‐trinitromethyl‐1<em>H</em>‐pyrazoles; and a discussion of the detonation properties of 30 polynitro compounds. No previous work has included such a broad set of compounds. While comparing experimental data with theoretical calculations does not guarantee agreement in advance, in our case, the accordance regarding geometries is very good, except for some observed discrepancies. In the section on detonation properties, the consonance in terms of densities, planarity, and heats of formation is less strong but still sufficient to draw interesting conclusions.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 10","pages":"Article e00400"},"PeriodicalIF":2.7,"publicationDate":"2025-10-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145317770","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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Synthesis of Benzopyrrolizinones via Photocycloaddition ‐ Dehydrogenative Aromatization Reactions of N‐(Trimethylsilyl)‐methylphthalimides with Electron Deficient Alkenes N-（三甲基硅基）-甲基邻苯二胺与缺电子烯烃的光环加成脱氢芳构化反应合成苯并吡咯利嗪酮

IF 2.7 4区化学

Asian Journal of Organic Chemistry Pub Date : 2025-10-01 DOI: 10.1002/ajoc.202500383

Suk Hyun Lim , Hayeon You , Dae Won Cho

{"title":"Synthesis of Benzopyrrolizinones via Photocycloaddition ‐ Dehydrogenative Aromatization Reactions of N‐(Trimethylsilyl)‐methylphthalimides with Electron Deficient Alkenes","authors":"Suk Hyun Lim , Hayeon You , Dae Won Cho","doi":"10.1002/ajoc.202500383","DOIUrl":"10.1002/ajoc.202500383","url":null,"abstract":"<div><div>Bridgehead nitrogen‐containing heterocycles, particularly pyrrolizinone derivatives, are prominent structural motifs commonly found in both naturally occurring alkaloids and synthetic bioactive molecules, exhibiting a wide range of distinctive biological activities. The broad pharmacological potential of pyrrolizinone scaffolds has motivated extensive efforts to develop efficient and versatile synthetic methods for their construction. In the present study, we reported stepwise photocycloaddition‐dehydrogenative aromatization reactions of <em>N</em>‐(silylmethyl)phthalimides and electron‐deficient alkenes to synthesize a series of benzopyrrolizinones, possessing various electron‐withdrawing substituents on either phenyl or pyrrole ring moieties. The key steps in these reactions include pathways involving visible light and thioxanthone (TXA)‐promoted 1,3‐dipolar cycloaddition between <em>N</em>‐(silylmethyl)phthalimides and electron‐deficient alkenes, followed by DDQ‐catalyzed dehydrogenative aromatization. The synthetic methods developed allow for the efficient and high‐yielding formation of benzopyrrolizinones under mild photochemical reaction conditions.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 10","pages":"Article e00383"},"PeriodicalIF":2.7,"publicationDate":"2025-10-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145317577","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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Electron Donating Group Effect on C─C Bond Scission Ability of Indanedione Dimers in Their Solution and Solid State 给电子基团对吲哚二酮二聚体在溶液和固态中C─C键断裂能力的影响

IF 2.7 4区化学

Asian Journal of Organic Chemistry Pub Date : 2025-10-01 DOI: 10.1002/ajoc.202500546

Yukina Yamamoto , Dr. Yumi Yakiyama , Dr. Tomohiko Nishiuchi , Prof. Dr. Takashi Kubo , Prof. Dr. Hidehiro Sakurai

{"title":"Electron Donating Group Effect on C─C Bond Scission Ability of Indanedione Dimers in Their Solution and Solid State","authors":"Yukina Yamamoto , Dr. Yumi Yakiyama , Dr. Tomohiko Nishiuchi , Prof. Dr. Takashi Kubo , Prof. Dr. Hidehiro Sakurai","doi":"10.1002/ajoc.202500546","DOIUrl":"10.1002/ajoc.202500546","url":null,"abstract":"<div><div>Light, heat and mechanical stress‐responsive molecules are of great interest in the field of modern materials chemistry. In this work, indanedione dimers <strong>1</strong>–<strong>3</strong> introduced with an electron‐donating thiophene group were designed with the expectation of easy cleavage of the central C─C single bond by the captodative effect. Our synthetic approach led to the successful preparation of dimethylthiophenyl and methylbenzothiophenyl derivatives <strong>1</strong> and <strong>2</strong>, while benzothiophenyl compound <strong>3</strong> was not formed; instead, the bridged product <strong>3'</strong> was obtained. The sequential UV–vis absorption and ESR measurements of <strong>1</strong> and <strong>2</strong> in the solution state confirmed the effectiveness of the presence of an electron‐donating group, which stabilized the radical form to realize a relatively low bond cleavage temperature. Meanwhile, it was also clarified that the bond scission event was strongly affected by the packing structure; much harder in the tightly packed crystalline <strong>1</strong> than its solution state, while almost the same as the solution state in the glassy solid of <strong>2</strong>, in which the intermolecular interaction should be much weaker and each molecule could move as easily as in the solution state. Further investigation of <strong>3'</strong> revealed the loss of bond scission ability by bridging.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 10","pages":"Article e00546"},"PeriodicalIF":2.7,"publicationDate":"2025-10-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145317638","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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Recent Advances in Transition Metal‐Catalyzed Synthesis of Bicyclo[4.1.0]heptenes from 1,6‐Enynes 过渡金属催化1,6-炔合成双环[4.1.0]庚烯的研究进展

IF 2.7 4区化学

Asian Journal of Organic Chemistry Pub Date : 2025-10-01 DOI: 10.1002/ajoc.70132

Dr. Perla Bharath Kumar , Pammi Venkata Rami Reddy , Sagar Pradip Patil , Dr. Raju Chittala Emmaniel , Dr. V. Karunakar Galla

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Design and Asymmetric Synthesis of Unnatural Amino Acid Derivatives Showing Staircase and Orientational Chirality 具有阶梯性和定向手性的非天然氨基酸衍生物的设计与不对称合成

IF 2.7 4区化学

Asian Journal of Organic Chemistry Pub Date : 2025-10-01 DOI: 10.1002/ajoc.70127

Anis Ur Rahman , Zishuo Zhang , Nighat Zarshad , Yue Zhang , Sai Zhang , Guigen Li , Asad Ali

{"title":"Design and Asymmetric Synthesis of Unnatural Amino Acid Derivatives Showing Staircase and Orientational Chirality","authors":"Anis Ur Rahman , Zishuo Zhang , Nighat Zarshad , Yue Zhang , Sai Zhang , Guigen Li , Asad Ali","doi":"10.1002/ajoc.70127","DOIUrl":"10.1002/ajoc.70127","url":null,"abstract":"<div><div>Amino acids are basic building blocks of peptides and proteins, which play essential roles in biological processes. Unnatural chiral amino acids have been proven to be powerful in drug design and discovery. Meanwhile, chirality has gained significant attention in the scientific community since it has been showing a profound impact on chemical, biomedical, and materials sciences. So far, chiral amino acids have been primarily built on center chirality, which governed secondary, tertiary, and higher conformational structures of peptides and proteins. Here in this work, we demonstrate the design and asymmetric synthesis of unnatural amino acids with a staircase and several other chirality elements. The architecture of staircase chirality is characterized by two symmetrical phenyl rings anchored by a naphthyl pier, with the rings asymmetrically displaced due to the influence of chiral auxiliaries at their para positions. Notably, as proven by X‐ray diffraction analysis, these staircase amino esters exhibit four distinct types of chirality: central, orientational, turbo, and staircase chirality, a chirality combination previously undocumented in the literature.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 10","pages":"Article e70127"},"PeriodicalIF":2.7,"publicationDate":"2025-10-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145317690","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