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Nitrogen Functionalization with <i>N</i>-(Fluorosulfonyl)carbamates 与&lt;i&gt;N&lt;/i&gt;-(氟磺酰基)氨基甲酸酯的氮功能化
4区 化学 Q4 CHEMISTRY, ORGANIC Pub Date : 2023-11-01 DOI: 10.5059/yukigoseikyokaishi.81.1081
Takuya Hashimoto
Carbon-nitrogen bond formation with ammonia or its equivalent has been a major research field in organic chemistry since the discovery of Wöhler’s urea synthesis. Given the versatility of nitrogen-doped organic molecules in natural products, pharmaceuticals, agrochemicals and materials, many such transformations have been conceived during the last 200 years. While the focus has shifted more and more to developing new catalysts rather than reagents to achieve this goal, over the last couple of years we have been intrigued by the possibility of inventing new ammonia equivalents which suit modern catalytic synthesis. We review herein our recent study triggered by this renewed interest in reagent design, which has led to the discovery and application of N-(fluorosulfonyl)carbamates as a new class of aminating reagents.
自发现Wöhler的尿素合成以来,与氨或其等价物形成碳氮键一直是有机化学的主要研究领域。考虑到氮掺杂有机分子在天然产品、药品、农用化学品和材料中的多功能性,在过去的200年里,人们设想了许多这样的转变。虽然焦点越来越多地转移到开发新的催化剂而不是试剂来实现这一目标,但在过去的几年里,我们对发明适合现代催化合成的新的氨当量的可能性很感兴趣。在此,我们回顾了最近在试剂设计方面的新兴趣所引发的研究,这导致了N-(氟磺酰基)氨基甲酸酯作为一类新的胺化试剂的发现和应用。
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引用次数: 0
Recent Progress on Metallo-Supramolecular Polymers and the Electrochromic Devices Fabrication 金属超分子聚合物与电致变色器件制备研究进展
4区 化学 Q4 CHEMISTRY, ORGANIC Pub Date : 2023-11-01 DOI: 10.5059/yukigoseikyokaishi.81.1089
Masayoshi Higuchi
This paper introduces our recent research on metallo-supramolecular polymers (MSPs) and the electrochromic (EC) device fabrication, including (1) control of metal sequence in one-dimensional (1D) MSPs, (2) design of two-dimensional (2D) MSPs, (3) three-dimensional (3D) hyperbranched MSPs, (4) EC devices (ECDs) with MSPs and (5) our trial for ECD applications. MSPs are a kind of coordination polymers and obtained by complexation of metal ions with multitopic organic ligands. MSPs show EC properties in the film state, activated by the electrochemical redox of the metal ions. The EC changes are caused by the reversible appearance and disappearance of the metal-to-ligand charge transfer (MLCT) absorption in the metal complex moieties of MSPs. ECDs with MSPs have great potential for the future’s smart window applications and spreading.
本文介绍了我们最近在金属超分子聚合物(MSPs)和电致变色(EC)器件制造方面的研究,包括:(1)一维(1D) MSPs中金属序列的控制,(2)二维(2D) MSPs的设计,(3)三维(3D)超支化MSPs,(4)带有MSPs的EC器件(ECDs)以及(5)我们在ECD应用方面的试验。MSPs是金属离子与多主题有机配体络合而成的一种配位聚合物。在金属离子的电化学氧化还原作用下,MSPs在薄膜状态下表现出EC特性。电导率的变化是由MSPs金属络合物中金属到配体电荷转移(MLCT)吸收的可逆出现和消失引起的。具有msp的ecd在未来的智能窗口应用和推广方面具有巨大的潜力。
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引用次数: 0
Synthetic Element Chemistry based on Precise Designs of Reagents and Transition States 基于试剂和过渡态精确设计的合成元素化学
4区 化学 Q4 CHEMISTRY, ORGANIC Pub Date : 2023-11-01 DOI: 10.5059/yukigoseikyokaishi.81.1096
Keiichi Hirano, Masanobu Uchiyama
In recent years, the use of various elements has been attracting large attention in drug discovery and materials science. Particularly, organoborons and organosilicons are promising candidates owing to their high stability and relatively low toxicity. However, there are still limitations in the available chemical structures and hence development of novel skeletal-constructing methods is an urgent task in synthetic chemistry. Based on precise designs of boron and silicon ate complexes through an integration of theoretical and experimental chemistry, we have developed novel boration and silylation reactions.
近年来,各种元素的使用在药物发现和材料科学中引起了很大的关注。特别是有机硼和有机硅,由于其高稳定性和相对较低的毒性,是有希望的候选人。然而,现有的化学结构仍然存在局限性,因此开发新的骨架构建方法是合成化学领域的一项紧迫任务。通过理论和实验化学的结合,精确设计了硼和硅盐配合物,我们开发了新的硼化和硅化反应。
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引用次数: 0
Use of Emerging C-H Functionalization Methods to Implement Strategies for the Divergent Total Syntheses of Bridged Polycyclic Natural Products 利用新兴的碳氢功能化方法实现桥接多环天然产物的发散全合成策略
4区 化学 Q4 CHEMISTRY, ORGANIC Pub Date : 2023-11-01 DOI: 10.5059/yukigoseikyokaishi.81.1028
Goh Sennari, Richmond Sarpong
Carbon-hydrogen (C-H) bonds are ubiquitous in complex natural products. Over the past three decades, many methods to convert C-H bonds distal from functional groups, which were generally considered inert, have been developed. These advances now enable selective peripheral functionalizations at a late-stage. The direct engagement of traditionally unreactive C-H bonds in reactions expands chemical space by reducing functional group interconversions. As such, C-H functionalization serves as a powerful tool in medicinal and agrocultural chemistry as well as in the total synthesis of natural products where diversification to a broad array of compounds from a common intermediate is often desired. In this Account, we detail the thought processes and design principles that relied on emerging methods for C-H functionalization to prepare a wide range of bridged, polycyclic, natural products in the cephalotane and longibornane families from a common intermediate in each case.
碳氢键在复杂的天然产物中普遍存在。在过去的三十年中,已经开发了许多方法来转换通常被认为是惰性的官能团远端的C-H键。这些进步现在可以在后期进行选择性外设功能化。传统上不反应的C-H键在反应中的直接参与通过减少官能团的相互转换扩大了化学空间。因此,碳氢化合物功能化在医药和农业化学以及天然产物的全合成中是一种强大的工具,在这些合成中,通常需要从一个共同的中间体多样化到广泛的化合物。在这篇文章中,我们详细介绍了依赖于新兴的碳氢功能化方法的思维过程和设计原则,在每种情况下,从一种常见的中间体中制备出广泛的桥接、多环、头孢烷和长硼烷家族的天然产物。
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引用次数: 0
Synthesis of Structurally Diverse Polycyclic Arenes Using Tandem Oxidative Ring Expansion Strategy 用串联氧化扩环策略合成结构多样的多环芳烃
4区 化学 Q4 CHEMISTRY, ORGANIC Pub Date : 2023-11-01 DOI: 10.5059/yukigoseikyokaishi.81.1062
Tienan Jin, Masahiro Terada
The impressive structural diversity of polycyclic arenes (PCAs) comprised of pentagon, hexagon, heptagon, and octagon rings has continued to drum up interest in the fields of synthetic chemistry and materials science owing to their tunable electronic properties in relation to their unique planar, twisted, and curved π-surface conformations. Although an array of synthetic strategies have been developed to construct both known and new PCA scaffolds in the past decades, flexible and expedient strategies for creating PCAs with differently sized rings embedded are rare. We describe herein our recent studies on the tandem oxidative ring expansion (TORE) strategy for the construction of structurally diverse PCAs involving intra- and intermolecular TORE reactions for hexagon-embedded PCAs, and intramolecular TORE reactions for O- or S-incorporated heptagon-embedded PCAs and octagon-embedded PCAs.
由五边形、六边形、七边形和八边形环组成的多环芳烃(PCAs)具有令人印象深刻的结构多样性,由于其独特的平面、扭曲和弯曲π面构象具有可调的电子性质,因此在合成化学和材料科学领域不断引起人们的兴趣。虽然在过去的几十年里,已经开发了一系列的合成策略来构建已知的和新的PCA支架,但用于制造嵌入不同大小环的PCA的灵活和方便的策略很少。本文描述了我们最近在构建结构多样的聚丙烯酸酯方面的串联氧化环扩张(TORE)策略的研究,包括六边形嵌入聚丙烯酸酯的分子内和分子间的TORE反应,以及O或s结合的七面嵌入聚丙烯酸酯和八边形嵌入聚丙烯酸酯的分子内TORE反应。
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引用次数: 0
Development of Homogeneous PNP-Ruthenium Complexes (Ru-MACHO Family) for Hydrogenation of Esters and Beyond 均相pnp -钌配合物(Ru-MACHO家族)在酯类及其他加氢反应中的应用
4区 化学 Q4 CHEMISTRY, ORGANIC Pub Date : 2023-11-01 DOI: 10.5059/yukigoseikyokaishi.81.1040
Osamu Ogata, Wataru Kuriyama
Development and applications of the Ru-MACHO family of ruthenium complexes are described. The parent Ru-MACHO was originally developed for catalytic reduction of esters by molecular hydrogen, which not only provides an environmentally benign and safe protocol, but also achieves a wide range of substrate scope. The reaction with methyl lactate was demonstrated on an industrial scale, producing 2,200 kg of 1,2-propanediol with high optical purity. In addition to hydrogenation of esters, the Ru-MACHO family catalyzes a variety of reactions, including hydrogenation of nitriles and sugars, dehydrogenation of alcohols, N-monomethylation of aromatic amines, and formal deoxygenative hydrogenation of lactams.
介绍了Ru-MACHO系列钌配合物的开发与应用。母体Ru-MACHO最初是为氢分子催化还原酯类而开发的,不仅提供了一种环保安全的方案,而且实现了广泛的底物范围。在工业规模上证实了与乳酸甲酯的反应,生产出2,200公斤具有高光学纯度的1,2-丙二醇。除了酯的加氢,Ru-MACHO家族还催化多种反应,包括腈和糖的加氢、醇的脱氢、芳香胺的n -单甲基化和内酰胺的形式脱氧加氢。
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引用次数: 0
Rapid Alternating Polarity as a Unique Tool for Synthetic Electrochemistry 快速交变极性作为合成电化学的独特工具
4区 化学 Q4 CHEMISTRY, ORGANIC Pub Date : 2023-11-01 DOI: 10.5059/yukigoseikyokaishi.81.1020
Yu Kawamata, Phil S. Baran
Electrosynthesis, driven by renewable energy, is a powerful method for accessing useful chemical reactivity in a sustainable fashion. Typically, electrochemical reactions have been carried out using direct current (DC), where electrons flow in a single direction. In contrast, utilization of alternating current (AC) has been largely unexplored in synthetic electrochemistry despite its wide applications in our daily life. This could stem from a historical perception regarding the lack of unique reactivity/selectivity that would result from using such a waveform, as well as the absence of readily available instrumentation to remove the engineering barrier for mass adoption. A breakthrough in this area is the introduction of rapid alternating polarity (rAP), which alternates the polarity of an electrode in the millisecond timescale. This mode of current delivery, now implemented in the widely employed potentiostat, ElectraSyn2.0, enables access to unique reactivity and selectivity in organic synthesis that are challenging or currently impossible to achieve by any known method (chemical or electrochemical). The remarkable chemoselectivity and simplicity of rAP open new vistas in modern synthetic electrochemistry.
由可再生能源驱动的电合成是一种以可持续的方式获得有用化学反应性的有力方法。通常,电化学反应是使用直流电(DC)进行的,其中电子沿单一方向流动。相比之下,尽管交流电在我们的日常生活中得到了广泛的应用,但它在合成电化学领域的应用还很少。这可能源于对使用这种波形缺乏独特反应性/选择性的历史认知,以及缺乏现成的仪器来消除大规模采用的工程障碍。该领域的一个突破是引入了快速交替极性(rAP),它可以在毫秒时间尺度内交替电极的极性。这种电流传递模式现已在广泛使用的恒电位器ElectraSyn2.0中实现,可以在有机合成中获得独特的反应性和选择性,这是目前任何已知方法(化学或电化学)都无法实现的。rAP具有显著的化学选择性和简单性,为现代合成电化学开辟了新的前景。
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引用次数: 0
Divergent Transformation of Carboxylic Acids through Photocatalytic Decarboxylation with Hypervalent Iodine Reagents 高价碘试剂光催化脱羧对羧酸的发散转化
4区 化学 Q4 CHEMISTRY, ORGANIC Pub Date : 2023-11-01 DOI: 10.5059/yukigoseikyokaishi.81.1050
Yota Sakakibara, Kenichiro Itami, Kei Murakami
Carboxylic acids are one of the most important functional groups found in various feedstocks. Their significance lies in their pivotal role as key intermediates in selective transformations during organic synthesis. Despite the existence of various decarboxylative transformation reactions such as Kolbe dimerization, these methods still exhibit certain limitations that present opportunities for further improvement. In this account, we present our recent studies on the application of photocatalytic decarboxylative transformation that allows the divergent transformation of carboxylic acids.
羧酸是各种原料中最重要的官能团之一。它们的意义在于它们作为有机合成过程中选择性转化的关键中间体的关键作用。尽管存在各种脱羧转化反应,如Kolbe二聚化,但这些方法仍然存在一定的局限性,这为进一步改进提供了机会。在这篇文章中,我们介绍了我们最近在光催化脱羧转化应用方面的研究,该转化允许羧酸的发散转化。
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引用次数: 0
Novel Estrogen Receptor Inhibitory Mechanism for Halogen-containing Endocrine-disrupting Chemicals Discovered by Computer Simulation 计算机模拟发现雌激素受体抑制含卤内分泌干扰物的新机制
4区 化学 Q4 CHEMISTRY, ORGANIC Pub Date : 2023-11-01 DOI: 10.5059/yukigoseikyokaishi.81.1103
Ayami Matsushima
Bisphenol A (BPA) is a component used in the manufacture of polycarbonate plastics and epoxy resins around the world; however, it is also well-known as one of the most notorious endocrine-disrupting chemicals. To avoid using BPA as an ingredient, various BPA derivatives and related compounds have been synthesized and the use of these for making polymers has grown significantly; however, the safety of these BPA derivatives, also known as next-generation bisphenols, has not been fully evaluated. We hypothesized that the bisphenol moiety is a privileged structure for binding to nuclear receptors. Here, we summarize the binding ability of next-generation bisphenols to estrogen receptors and show that halogen-containing bisphenols act as coactivator binding inhibitors for estrogen receptor β.
双酚A (BPA)是世界各地用于制造聚碳酸酯塑料和环氧树脂的一种成分;然而,它也是众所周知的最臭名昭著的内分泌干扰化学物质之一。为了避免使用双酚a作为一种成分,人们合成了各种双酚a衍生物和相关化合物,这些衍生物和化合物用于制造聚合物的用途显著增加;然而,这些双酚a衍生物(也被称为下一代双酚类物质)的安全性尚未得到充分评估。我们假设双酚部分是与核受体结合的特权结构。本文总结了新一代双酚类化合物与雌激素受体的结合能力,并表明含卤双酚类化合物可作为雌激素受体β的辅激活剂结合抑制剂。
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引用次数: 0
Enthusiasm, Guiding the Way to Universal Catalysts? 热情,引领通往通用催化剂之路?
4区 化学 Q4 CHEMISTRY, ORGANIC Pub Date : 2023-11-01 DOI: 10.5059/yukigoseikyokaishi.81.1019
Benjamin List
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引用次数: 0
期刊
Journal of Synthetic Organic Chemistry Japan
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