首页 > 最新文献

Asian Journal of Organic Chemistry最新文献

英文 中文
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 Q1 CHEMISTRY, ORGANIC Pub Date : 2024-10-01 DOI: 10.1002/ajoc.202400194
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 V5+ was crucial for the effective activation of the ortho position.
通过苯酚与苯胺衍生物直接和高选择性的 V 催化邻氨基甲基化反应,开发了一种 C(sp2)-C(sp3)交叉脱氢偶联策略。在温和的反应条件下,获得了一系列氨甲基苯酚化合物,收率从中等到良好,底物范围广泛。研究人员提出了一种可能的自由基机理,并发现酚羟基与 V5+ 的配位是有效激活正位的关键。
{"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 Q1 CHEMISTRY, ORGANIC Pub Date : 2024-10-01 DOI: 10.1002/ajoc.202400219
Rohit Kumar Maurya , Vikash Kumar , Ashutosh Dey , Shubham Kumar , Dr. Mahender Khatravath
A highly efficient, convenient and ecofriendly approach to access highly functionalized 2H‐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 (SiO2‐OSO3H, SSA) coupled with microwave irradiation. This reaction was well tolerated for various substituents including different functional groups and furnished the desired highly functionalized 2H‐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.
从容易获得的炔拴 2-((3-苯基丙-2-炔-1-基)氧基)苯甲醛开始,在二氧化硅硫酸(SiO2-OSO3H,SSA)和微波辐照的催化下,建立了一种通过分子内醛炔元合成反应获得高官能度 2H-铬烯的高效、便捷和生态友好的方法。这种反应对包括不同官能团在内的各种取代基都有很好的耐受性,并能在很短的时间内以良好到极好的收率获得所需的高官能度 2H-chromene 衍生物。对传统加热方法和微波辐照进行了系统研究,以证明微波辅助条件在高产率和缩短反应时间方面的优势。
{"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 Q1 CHEMISTRY, ORGANIC Pub Date : 2024-10-01 DOI: 10.1002/ajoc.202400264
Mengyao Zhang , Shiyu Wang , Hongli Wu , Genping Huang
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 η3‐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 Z/E‐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.
为了研究钯催化的 1,4 二烯与常见胺的烯丙基 C-H 氨化反应,我们进行了密度泛函理论计算。计算结果表明,反应开始时,烯丙基 C-H 键通过质子和双电子协同转移过程裂解,形成 h3-烯丙基 Pd(II) 物种。研究发现,随后形成的 C-N 键与亲核体的碱性有很大关系,因此在改变亲核体时可以实现区域选择性转换。对于弱碱性芳香胺,反应是通过氢键促成的内圈亲核攻击途径发生的。反应碳原子与末端碳原子之间的距离决定了 Z/E 选择性。区域选择性主要是由于烯丙基和配体之间的立体斥力。另一方面,在与碱性较强的脂肪族环胺反应时,外层亲核攻击途径更受青睐。研究发现,烯丙基配位方式的改变在决定区域选择性方面起着至关重要的作用。
{"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 Q1 CHEMISTRY, ORGANIC Pub Date : 2024-10-01 DOI: 10.1002/ajoc.202400304
Alexey M. Starosotnikov , Maxim A. Bastrakov
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.
二硝基吡啶是一类前景广阔的杂环化合物。它们被认为是炸药、高能化合物、农用化学品、生物传感器和生物活性化合物的有用前体,具有多种特性:抗肿瘤、抗病毒、抗神经退行性病变。对文献数据的初步分析表明,在过去几十年中,多硝基吡啶化学一直在积极发展。每年发表的论文数量稳步增长就证明了这一点。本综述分析了 2010-2024 年间有关异构二硝基吡啶的合成、反应和实际应用的文献。
{"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 Q1 CHEMISTRY, ORGANIC Pub Date : 2024-10-01 DOI: 10.1002/ajoc.202400193
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.
迈克尔加成反应是当代有机合成的基石,由于它能够形成复杂的碳-碳键和碳-异原子键,因此再次引起了人们的兴趣。在过去几年中,杂环化合物因其结构的多样性和独特的反应活性,无论是否存在碱/过渡金属/有机催化剂,都被严格用作迈克尔供体。本综述囊括了以杂环化合物为迈克尔供体进行迈克尔加成反应的最新化学突破。它全面介绍了 2017 年以来由强效杂环引发的迈克尔加成反应的最新进展,重点介绍了新颖和创新的方法,并提出了战略性见解。
{"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 Q1 CHEMISTRY, ORGANIC Pub Date : 2024-10-01 DOI: 10.1002/ajoc.202400270
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.
对二氧化钛纳米材料进行聚合物改性可在二氧化钛表面提供介质分散性和各种功能。在此,我们报告了在不对二氧化钛进行任何预处理的情况下,通过紫外线(UV)辐照自由基聚合对二氧化钛纳米管(TNTs)和二氧化钛纳米颗粒(TNPs)表面进行直接原位聚合物改性的方法。所得到的聚合物改性 TNTs 和 TNPs 在溶剂中分散良好。利用傅立叶变换红外光谱、热重分析和扫描电子显微镜-能量色散 X 射线光谱等多种技术对产品进行的表征证实,通过紫外光照射自由基聚合产生的聚合物成功地改性了 TNT 和 TNP 的表面。使用氢氟酸溶解二氧化钛,分离出二氧化钛表面的聚合物,并通过尺寸排阻色谱法和基质辅助激光解吸/电离飞行时间质谱法进行分析。在紫外线照射下,聚合物改性的 TNTs 和 TNPs 在降解染料方面保持了光催化活性。此外,利用紫外辐照聚合体系还成功制备了糖聚合物改性 TNTs。糖聚合物在 TNT 表面保持了凝集素的亲和性。
{"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 Q1 CHEMISTRY, ORGANIC Pub Date : 2024-10-01 DOI: 10.1002/ajoc.202400182
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.
将疏水性药物封装到多糖载体中可提高其水溶性、生物相容性、肿瘤特异性蓄积和治疗效果。本研究通过酰胺缩合反应将苯硼酸(PBA)锚定在生物相容性多糖透明质酸(HA)的链上,从而制备出刺激响应型靶向给药系统。通过硼酸盐交联 PBA 与卡培他滨(CAPE)和阿糖胞苷(Al)等含二元醇的抗癌药物,制备了一系列由疏水性药物核心和亲水性透明质酸外壳组成的 pH 响应型共轭透明质酸纳米粒子。通过使用这种多糖载体,在酸性 pH 条件下实现了令人满意的靶向药物释放行为,降低了细胞毒性,提高了抗癌效果。相信这一策略在多糖改性和抗癌相关应用方面具有巨大潜力。
{"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 Q1 CHEMISTRY, ORGANIC Pub Date : 2024-10-01 DOI: 10.1002/ajoc.202400301
Javier Santamaría , Patricia García‐Martínez , Luis A. López
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.
功能化二茂铁衍生物在各个科学领域都有广泛的应用。尽管在合成 1,2-二茂铁衍生物方面取得了重大进展,但 1,3-二茂铁的制备仍然具有挑战性。不过,最近有报道称,1,3-二取代二茂铁有几种强大的合成方法。本综述旨在介绍这些合成方法的演变,从最初的化学计量学方法到最近的催化方法。
{"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 Q1 CHEMISTRY, ORGANIC Pub Date : 2024-10-01 DOI: 10.1002/ajoc.202400250
Fayu Wang , Hongjie Li , Shuai Huang , Rong Zou , Gang Chang , Hanping He
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 10−2 cm2 V−1 S−1 along with an Ion/Ioff ratio of 8.39×103, demonstrating exceptional field‐effect performance.
异靛蓝及其衍生物作为广泛应用的缺电子分子,在有机场效应晶体管中得到了广泛的应用,并迅速引起了人们的关注。本研究通过四种不同侧链的异靛蓝分子作为受体和噻吩作为供体的 Stille 偶联反应,合成了四种不同的异靛蓝基有机半导体聚合物。此外,还对它们的光学、电化学、热稳定性和其他相关特性进行了全面评估。这些聚合物的 LUMO 能级较低,有利于半导体层与源极/漏极之间的有效电接触,同时确保了半导体聚合物在空气中的出色稳定性,因此表现出了出色的电化学和热稳定性。此外,利用这些聚合物制备的溶液栅场效应晶体管的空穴迁移率达到了 10-2 cm2V-1S-1,离子/间隙比为 8.39×103,显示出卓越的场效应性能。
{"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 Q1 CHEMISTRY, ORGANIC Pub Date : 2024-09-20 DOI: 10.1002/ajoc.202400376
Mieko Arisawa, Hiiro Otsuka, Tomoko Idogawa, Kyosuke Sawahata, Yasutaka Kawai
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.
在回流四氢呋喃中,铑催化的环-(PPh)5 与炔烃的加成反应可有效地生成 1,2,3-三膦烯,其中 -PPh-PPh-PPh- 基团通过 P-P 键的裂解从环-(PPh)5 中转移出来。在回流氯苯中,反应伴随着 1,2-二磷酸盐的形成。当含有 P-P 键的三磷烯在铑催化条件下与活性炔烃反应时,会得到不对称的磷烯。铑催化反应可用于合成具有不同磷原子数的各种含磷杂环。
{"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
期刊
Asian Journal of Organic Chemistry
全部 Acc. Chem. Res. ACS Applied Bio Materials ACS Appl. Electron. Mater. ACS Appl. Energy Mater. ACS Appl. Mater. Interfaces ACS Appl. Nano Mater. ACS Appl. Polym. Mater. ACS BIOMATER-SCI ENG ACS Catal. ACS Cent. Sci. ACS Chem. Biol. ACS Chemical Health & Safety ACS Chem. Neurosci. ACS Comb. Sci. ACS Earth Space Chem. ACS Energy Lett. ACS Infect. Dis. ACS Macro Lett. ACS Mater. Lett. ACS Med. Chem. Lett. ACS Nano ACS Omega ACS Photonics ACS Sens. ACS Sustainable Chem. Eng. ACS Synth. Biol. Anal. Chem. BIOCHEMISTRY-US Bioconjugate Chem. BIOMACROMOLECULES Chem. Res. Toxicol. Chem. Rev. Chem. Mater. CRYST GROWTH DES ENERG FUEL Environ. Sci. Technol. Environ. Sci. Technol. Lett. Eur. J. Inorg. Chem. IND ENG CHEM RES Inorg. Chem. J. Agric. Food. Chem. J. Chem. Eng. Data J. Chem. Educ. J. Chem. Inf. Model. J. Chem. Theory Comput. J. Med. Chem. J. Nat. Prod. J PROTEOME RES J. Am. Chem. Soc. LANGMUIR MACROMOLECULES Mol. Pharmaceutics Nano Lett. Org. Lett. ORG PROCESS RES DEV ORGANOMETALLICS J. Org. Chem. J. Phys. Chem. J. Phys. Chem. A J. Phys. Chem. B J. Phys. Chem. C J. Phys. Chem. Lett. Analyst Anal. Methods Biomater. Sci. Catal. Sci. Technol. Chem. Commun. Chem. Soc. Rev. CHEM EDUC RES PRACT CRYSTENGCOMM Dalton Trans. Energy Environ. Sci. ENVIRON SCI-NANO ENVIRON SCI-PROC IMP ENVIRON SCI-WAT RES Faraday Discuss. Food Funct. Green Chem. Inorg. Chem. Front. Integr. Biol. J. Anal. At. Spectrom. J. Mater. Chem. A J. Mater. Chem. B J. Mater. Chem. C Lab Chip Mater. Chem. Front. Mater. Horiz. MEDCHEMCOMM Metallomics Mol. Biosyst. Mol. Syst. Des. Eng. Nanoscale Nanoscale Horiz. Nat. Prod. Rep. New J. Chem. Org. Biomol. Chem. Org. Chem. Front. PHOTOCH PHOTOBIO SCI PCCP Polym. Chem.
×
引用
GB/T 7714-2015
复制
MLA
复制
APA
复制
导出至
BibTeX EndNote RefMan NoteFirst NoteExpress
×
0
微信
客服QQ
Book学术公众号 扫码关注我们
反馈
×
意见反馈
请填写您的意见或建议
请填写您的手机或邮箱
×
提示
您的信息不完整,为了账户安全,请先补充。
现在去补充
×
提示
您因"违规操作"
具体请查看互助需知
我知道了
×
提示
现在去查看 取消
×
提示
确定
Book学术官方微信
Book学术文献互助
Book学术文献互助群
群 号:481959085
Book学术
文献互助 智能选刊 最新文献 互助须知 联系我们:info@booksci.cn
Book学术提供免费学术资源搜索服务,方便国内外学者检索中英文文献。致力于提供最便捷和优质的服务体验。
Copyright © 2023 Book学术 All rights reserved.
ghs 京公网安备 11010802042870号 京ICP备2023020795号-1