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V–Catalyzed Direct Ortho‐Aminomethylation of Phenols V 催化苯酚的直接正氨甲基化反应
IF 2.8 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2024-10-01 DOI: 10.1002/ajoc.202400194
{"title":"V–Catalyzed Direct Ortho‐Aminomethylation of Phenols","authors":"","doi":"10.1002/ajoc.202400194","DOIUrl":"10.1002/ajoc.202400194","url":null,"abstract":"<div><div>A strategy for cross‐dehydrogenative C(sp2)‐C(sp3) coupling was developed by direct and highly selective V‐catalyzed ortho‐aminomethylation of phenol with aniline derivatives. A series of aminomethylphenol compounds were obtained in moderate to good yields under mild reaction conditions and with a broad substrate scope. A possible radical mechanism was proposed, and it was found that the coordination of phenolic hydroxyl groups with V<sup>5+</sup> was crucial for the effective activation of the ortho position.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"13 10","pages":"Article e202400194"},"PeriodicalIF":2.8,"publicationDate":"2024-10-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141586071","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
Silica Sulphuric Acid Catalyzed Intra‐Molecular Alkyne Carbonyl Metathesis (ACM): A Rapid Access to 2H‐Chromenes 二氧化硅硫酸催化的分子内炔羰基复分解反应 (ACM)：快速获得 2H- Chromenes
IF 2.8 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2024-10-01 DOI: 10.1002/ajoc.202400219
Rohit Kumar Maurya , Vikash Kumar , Ashutosh Dey , Shubham Kumar , Dr. Mahender Khatravath
{"title":"Silica Sulphuric Acid Catalyzed Intra‐Molecular Alkyne Carbonyl Metathesis (ACM): A Rapid Access to 2H‐Chromenes","authors":"Rohit Kumar Maurya ,&nbsp;Vikash Kumar ,&nbsp;Ashutosh Dey ,&nbsp;Shubham Kumar ,&nbsp;Dr. Mahender Khatravath","doi":"10.1002/ajoc.202400219","DOIUrl":"10.1002/ajoc.202400219","url":null,"abstract":"<div><div>A highly efficient, convenient and ecofriendly approach to access highly functionalized <em>2H</em>‐chromenes via intramolecular aldehyde alkyne metathesis reaction was established starting from readily accessible alkyne‐tethered 2‐((3‐phenylprop‐2‐yn‐1‐yl) oxy)benzaldehydes and catalyzed by silica sulfuric acid (SiO<sub>2</sub>‐OSO<sub>3</sub>H, SSA) coupled with microwave irradiation. This reaction was well tolerated for various substituents including different functional groups and furnished the desired highly functionalized 2<em>H</em>‐chromene derivatives in good to excellent yields in a very short time. A systematic study of the conventional heating approach and microwave irradiation was performed to demonstrate the advantages of the microwave‐assisted condition in terms of high yield and shorter reaction time.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"13 10","pages":"Article e202400219"},"PeriodicalIF":2.8,"publicationDate":"2024-10-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141609398","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
Mechanism and Origins of Nucleophile‐Controlled Regioselectivity of Palladium‐Catalyzed Allylic C−H Amination of 1,4‐Dienes: A Computational Study 钯催化 1,4-二烯的烯丙基 C-H 氨基化的核亲和剂控制的区域选择性的机理和起源：计算研究
IF 2.8 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2024-10-01 DOI: 10.1002/ajoc.202400264
Mengyao Zhang , Shiyu Wang , Hongli Wu , Genping Huang
{"title":"Mechanism and Origins of Nucleophile‐Controlled Regioselectivity of Palladium‐Catalyzed Allylic C−H Amination of 1,4‐Dienes: A Computational Study","authors":"Mengyao Zhang ,&nbsp;Shiyu Wang ,&nbsp;Hongli Wu ,&nbsp;Genping Huang","doi":"10.1002/ajoc.202400264","DOIUrl":"10.1002/ajoc.202400264","url":null,"abstract":"<div><div>Density functional theory calculations have been conducted to investigate the palladium‐catalyzed allylic C−H amination of 1,4‐dienes with commonly available amines. The computations indicate that the reaction begins with the allylic C−H bond cleavage through the concerted proton and two‐electron transfer process to forge the η<sup>3</sup>‐allyl Pd(II) species. The ensuing C−N bond formation was found to be highly dependent on the basicity of the nucleophile, enabling the regioselectivity switch upon change of the nucleophile. With the weakly basic aromatic amine, the reaction occurs through the hydrogen‐bonding enabled inner‐sphere nucleophilic attack pathway. The distance between the reacting carbon atom and the terminal carbon atom is responsible for the <em>Z</em>/<em>E</em>‐selectivity. The regioselectivity is primarily due to steric repulsion between the allyl group and the ligand. On the other hand, the outer‐sphere nucleophilic attack pathway is favored for the reaction with the more basic aliphatic cyclic amine. The change of the coordinating mode of the allylic moiety was found to play a crucial role in determining the regioselectivity.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"13 10","pages":"Article e202400264"},"PeriodicalIF":2.8,"publicationDate":"2024-10-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141783925","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
Dinitropyridines: Synthesis and Reactions 二硝基吡啶：合成与反应
IF 2.8 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2024-10-01 DOI: 10.1002/ajoc.202400304
Alexey M. Starosotnikov , Maxim A. Bastrakov
{"title":"Dinitropyridines: Synthesis and Reactions","authors":"Alexey M. Starosotnikov ,&nbsp;Maxim A. Bastrakov","doi":"10.1002/ajoc.202400304","DOIUrl":"10.1002/ajoc.202400304","url":null,"abstract":"<div><div>Dinitropyridines are one of the promising classes of heterocyclic compounds. They are considered as useful precursors of explosives and energetic compounds, agrochemicals, biosensors and biologically active compounds with diverse properties: antitumor, antiviral, anti‐neurodegenerative. Preliminary analysis of literature data shows that the chemistry of polynitropyridines has been actively developing over the past few decades. This is evidenced by the steadily growing annual number of publications. In this review the literature on the synthesis, reactions and practical application of isomeric dinitropyridines over a period of 2010–2024 is analyzed.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"13 10","pages":"Article e202400304"},"PeriodicalIF":2.8,"publicationDate":"2024-10-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141872244","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
Current Developments in Michael Addition Reaction using Heterocycles as Convenient Michael Donors 利用杂环作为方便的迈克尔供体进行迈克尔加成反应的最新进展
IF 2.8 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2024-10-01 DOI: 10.1002/ajoc.202400193
{"title":"Current Developments in Michael Addition Reaction using Heterocycles as Convenient Michael Donors","authors":"","doi":"10.1002/ajoc.202400193","DOIUrl":"10.1002/ajoc.202400193","url":null,"abstract":"<div><div>The Michael addition reaction, a cornerstone of contemporary organic synthesis, has witnessed a resurgence of interest owing to its ability to forge intricate carbon‐carbon and carbon‐heteroatom bonds. In the past few years, heterocyclic compounds have been rigorously used as Michael donors, owing to their architectural diversity and distinct reactivity with or without the presence of base/transition metals/organocatalysts. This review encapsulates the latest breakthroughs in chemistry involving Michael addition reaction using heterocyclic compounds as Michael donors. It delivers a comprehensive update on developments in Michael addition reaction triggered by potent heterocycles since 2017, highlighting novel and innovative methodologies, with strategic insights.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"13 10","pages":"Article e202400193"},"PeriodicalIF":2.8,"publicationDate":"2024-10-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141547854","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
Direct In Situ Polymer Modification of Titania Nanomaterial Surfaces via UV‐irradiated Radical Polymerization 通过紫外线辐射辐射聚合对二氧化钛纳米材料表面进行直接原位聚合物改性
IF 2.8 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2024-10-01 DOI: 10.1002/ajoc.202400270
{"title":"Direct In Situ Polymer Modification of Titania Nanomaterial Surfaces via UV‐irradiated Radical Polymerization","authors":"","doi":"10.1002/ajoc.202400270","DOIUrl":"10.1002/ajoc.202400270","url":null,"abstract":"<div><div>Polymer modification of titania nanomaterials can provide media dispersibility and various functionalities onto the titania surface. Herein, we report the direct in situ polymer modification of the surface of titania nanotubes (TNTs) and titania nanoparticles (TNPs) via ultraviolet (UV)‐irradiated radical polymerization without any pretreatment of titania. The resulting polymer‐modified TNTs and TNPs dispersed well in solvents. The characterization of the products using various techniques including Fourier transform infrared spectroscopy, thermogravimetric analysis, and scanning electron microscopy‐energy dispersive X‐ray spectroscopy confirmed the successful modification of the TNT and TNP surfaces by the polymers produced via UV‐irradiated radical polymerization. The polymers on the titania surface were isolated by dissolving titania using hydrofluoric acid and analyzed by means of size exclusion chromatography and matrix‐assisted laser desorption/ionization‐time of flight‐mass spectrometry. The polymer‐modified TNTs and TNPs maintained their photocatalytic activity in dye degradation under UV irradiation. Moreover, glycopolymer‐modified TNTs were successfully prepared using the UV‐irradiated polymerization system. The glycopolymer retained its lectin biding affinity on the TNT surface.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"13 10","pages":"Article e202400270"},"PeriodicalIF":2.8,"publicationDate":"2024-10-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141520291","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
Phenylboronic Acid‐Functionalized Hyaluronic Acid as Polysaccharide Carriers for Diol‐Containing Drugs Delivery 苯基硼酸官能化透明质酸作为多糖载体用于含二醇药物的输送
IF 2.8 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2024-10-01 DOI: 10.1002/ajoc.202400182
{"title":"Phenylboronic Acid‐Functionalized Hyaluronic Acid as Polysaccharide Carriers for Diol‐Containing Drugs Delivery","authors":"","doi":"10.1002/ajoc.202400182","DOIUrl":"10.1002/ajoc.202400182","url":null,"abstract":"<div><div>Packaging hydrophobic drugs into polysaccharide carriers can improve their aqueous solubility, biocompatibility, tumor‐specific accumulation, and therapeutic effect. In this work, phenylboronic acid (PBA) was anchored onto the chain of biocompatible polysaccharide hyaluronic acid (HA) by an amide condensation reaction, which could be used to fabricate stimuli‐responsive targeted drug delivery systems. A series of pH‐responsive conjugated hyaluronic acid nanoparticles composed of a hydrophobic drug core and hydrophilic hyaluronic acid shell were prepared by the boronate‐crosslink of the PBA with diol‐containing anticancer drugs such as capecitabine (CAPE) and aloin (Al). Satisfactory targeted drug release behavior at acidic pH, lower cytotoxicity, and higher anticancer effect were realized by using this polysaccharide carrier. It is believed that this strategy has great potential for polysaccharide modification and anticancer‐associated applications.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"13 10","pages":"Article e202400182"},"PeriodicalIF":2.8,"publicationDate":"2024-10-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141569388","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
Advances in the Synthesis of 1,3‐Disubstituted Ferrocene Derivatives: From Stoichiometric to Catalytic Methods 1,3-二取代二茂铁衍生物的合成进展：从计量方法到催化方法
IF 2.8 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2024-10-01 DOI: 10.1002/ajoc.202400301
Javier Santamaría , Patricia García‐Martínez , Luis A. López
{"title":"Advances in the Synthesis of 1,3‐Disubstituted Ferrocene Derivatives: From Stoichiometric to Catalytic Methods","authors":"Javier Santamaría ,&nbsp;Patricia García‐Martínez ,&nbsp;Luis A. López","doi":"10.1002/ajoc.202400301","DOIUrl":"10.1002/ajoc.202400301","url":null,"abstract":"<div><div>Functionalized ferrocene derivatives have a wide range of applications across various scientific fields. Although significant progress has been made in synthesizing 1,2‐disubstituted ferrocene derivatives, the preparation of 1,3‐disubstituted ferrocenes remains challenging. Recently, however, several powerful synthetic approaches to 1,3‐disubstituted ferrocenes have been reported. This review aims to present the evolution of these synthetic methods, from initial stoichiometric approaches to the more recent catalytic methodologies.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"13 10","pages":"Article e202400301"},"PeriodicalIF":2.8,"publicationDate":"2024-10-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/ajoc.202400301","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141784137","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Synthesis and Performance of Bithiophene Isoindigo Organic Semiconductors with Side‐Chain Functionality in Transistors 晶体管中具有侧链功能的噻吩异靛蓝有机半导体的合成与性能
IF 2.8 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2024-10-01 DOI: 10.1002/ajoc.202400250
Fayu Wang , Hongjie Li , Shuai Huang , Rong Zou , Gang Chang , Hanping He
{"title":"Synthesis and Performance of Bithiophene Isoindigo Organic Semiconductors with Side‐Chain Functionality in Transistors","authors":"Fayu Wang ,&nbsp;Hongjie Li ,&nbsp;Shuai Huang ,&nbsp;Rong Zou ,&nbsp;Gang Chang ,&nbsp;Hanping He","doi":"10.1002/ajoc.202400250","DOIUrl":"10.1002/ajoc.202400250","url":null,"abstract":"<div><div>The isoindigo and its derivatives have rapidly garnered attention as widely employed electron‐deficient moieties, finding extensive applications in organic field‐effect transistors. In this study, four different isoindigo‐based organic semiconductor polymers were synthesized via a Stille coupling reaction of four isoindigo molecules with varying side chains serving as acceptors and bithiophene as donors. Furthermore, their optical, electrochemical, thermal stability, and other relevant properties were comprehensively evaluated. These polymers exhibited remarkable electrochemical and thermal stability attributed to their low LUMO energy level, which facilitates effective electrical contact between the semiconductor layer and the source/drain while ensuring excellent air stability for the semiconductor polymers. Additionally, solution‐gate field‐effect transistors prepared using these polymers achieved hole mobilities of 10<sup>−2</sup> cm<sup>2</sup> V<sup>−1</sup> S<sup>−1</sup> along with an I<sub>on</sub>/I<sub>off</sub> ratio of 8.39×10<sup>3</sup>, demonstrating exceptional field‐effect performance.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"13 10","pages":"Article e202400250"},"PeriodicalIF":2.8,"publicationDate":"2024-10-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141872245","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
Synthesis of 1,2,3-Triphospholenes, 1,2-Diphosphetes, and Unsymmetric Phospholes by Rhodium-catalyzed Cleavage of P–P Bonds and Addition to Alkynes 通过铑催化的 P-P 键裂解和与炔烃的加成合成 1,2,3-三磷烯、1,2-二磷烯和不对称磷烯
IF 2.7 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2024-09-20 DOI: 10.1002/ajoc.202400376
Mieko Arisawa, Hiiro Otsuka, Tomoko Idogawa, Kyosuke Sawahata, Yasutaka Kawai
{"title":"Synthesis of 1,2,3-Triphospholenes, 1,2-Diphosphetes, and Unsymmetric Phospholes by Rhodium-catalyzed Cleavage of P–P Bonds and Addition to Alkynes","authors":"Mieko Arisawa, Hiiro Otsuka, Tomoko Idogawa, Kyosuke Sawahata, Yasutaka Kawai","doi":"10.1002/ajoc.202400376","DOIUrl":"https://doi.org/10.1002/ajoc.202400376","url":null,"abstract":"The rhodium-catalyzed addition reaction of cyclo-(PPh)5 to alkynes in refluxing THF efficiently provide 1,2,3-triphospholenes, in which the –PPh–PPh–PPh– group is transferred from cyclo-(PPh)5 by the cleavage of P–P bonds. In refluxing chlorobenzene, the reactions are accompanied by the formation of 1,2-diphosphetes. When the triphospholenes containing P–P bonds are reacted with reactive alkynes under rhodium-catalyzed conditions, unsymmetric phospholes are obtained. The rhodium-catalyzed reactions can be used to synthesize various phosphorus-containing heterocycles with different numbers of phosphorus atoms.","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"52 1","pages":""},"PeriodicalIF":2.7,"publicationDate":"2024-09-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142269102","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
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