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Brønsted acid-promoted synthesis of polysubstituted pyrroles from enamines/imines and diazopyruvates: A metal-free cascade approach 在布氏酸的促进下,从烯胺/亚胺和重氮丙酮酸盐合成多代吡咯:一种无金属级联方法
Pub Date : 2025-02-01 Epub Date: 2023-12-13 DOI: 10.1016/j.gresc.2023.12.002
Farrukh Sajjad , Ming-Hua Xu
A Brønsted acid-promoted, metal-free cascade reaction of easily available enamines/imines with diazopyruvates has been demonstrated. With triflic acid as the promoter, the reaction proceeds smoothly at room temperature through sequential diazo protonation, nucleophilic enamine N-addition/C-addition and dehydrative aromatisation in a highly regioselective manner. Interestingly, the regioselectivity of the reaction is governed by the unusual enamine N-nucleophilic addition. The method provides an operationally trivial approach to the synthesis of multisubstituted pyrroles including tri-, tetra-, and penta-substituted derivatives as well as N–H free pyrroles with diverse functionalities in good yields under extraordinarily simple and mild conditions. The utility of the method is illustrated by the rapid assembly of polysubstituted bispyrroles and an array of diversely structured pyrrole derivatives.
研究人员展示了一种由勃氏酸促进的、不含金属的级联反应,该反应是将易于获得的烯胺/亚胺与重氮丙酮酸盐进行反应。以三氟丙烯酸为促进剂,该反应在室温下以高度区域选择性的方式,通过重氮质子化、亲核烯胺 N-加成/C-加成和脱水芳香化的顺序顺利进行。有趣的是,该反应的区域选择性是由不寻常的烯胺 N-亲核加成决定的。该方法为合成多取代吡咯(包括三、四和五取代衍生物)以及具有不同官能度的 N-H 游离吡咯提供了一种操作简便的方法,而且条件异常简单温和。通过快速组装多取代双吡咯和一系列结构多样的吡咯衍生物,说明了该方法的实用性。
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引用次数: 0
Chemo- and diastereoselective four-component reactions with Rh carbynoids Rh类碳的化学和非对映选择性四组分反应
Pub Date : 2025-02-01 Epub Date: 2024-10-28 DOI: 10.1016/j.gresc.2024.10.006
Mengchu Zhang , Xiaoyan Yang , Xiang Fu , Xiaoyu Zhou , Yu Qian , Wenhao Hu
Multi-component reactions (MCRs) provide an efficient method for constructing multiple chemical bonds by combining three or more starting materials in a single operational step, enabling rapid and cost-effective synthesis of structurally diverse compounds. Although carbynoids (R-C:+) have shown potential for the development of selective MCRs due to their unique carbene and carbocation characteristics, their application in four-component reactions (4CRs) has been constrained by challenges in chemoselectivity. Herein, we provide a general solution to the challenges of chemoselective 4CR, using halo diazo reagents as carbynoid precursors, followed by reacting with pyrazoles, alcohols and imines sequentially. This approach allows the simultaneous construction of three different C (sp3)-N, C (sp3)-O, and C (sp3)-C (sp3) bonds on the same carbon. The success of this protocol mainly depends on precise control of chemical kinetics. Detailed experimental studies elucidate that the generation rate of aza-Rh(II)-carbene is faster than oxy-Rh(II)-carbene.
多组分反应(Multi-component reactions, mcr)提供了一种通过在一个操作步骤中结合三种或三种以上的起始物质来构建多个化学键的有效方法,使快速、经济地合成结构多样的化合物成为可能。虽然羰基化合物(R-C:+)由于其独特的碳和碳正离子特性而显示出发展选择性mcs的潜力,但其在四组分反应(4cr)中的应用受到化学选择性挑战的限制。在此,我们提供了一个解决化学选择性4CR挑战的通用解决方案,使用halo重氮试剂作为类碳前体,然后依次与吡唑、醇和亚胺反应。这种方法允许在同一碳上同时构建三个不同的C (sp3)-N, C (sp3)-O和C (sp3)-C (sp3)键。该方案的成功主要取决于化学动力学的精确控制。详细的实验研究表明,aza-Rh(II)-carbene的生成速度比氧- rh (II)-carbene快。
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引用次数: 0
Sustainable synthetic routes to deuterium-labelled organic compounds using immobilized and recyclable (bio)catalysts 可持续合成路线,以氘标记的有机化合物使用固定化和可回收(生物)催化剂
Pub Date : 2025-02-01 Epub Date: 2024-10-03 DOI: 10.1016/j.gresc.2024.09.008
Luka Jedlovčnik , Jakob Höfferle , Aljaž Gaber , Fjoralb Pashaj , Jerneja Kladnik , Janez Košmrlj , Volker Derdau , Ross D. Jansen-van Vuuren
Deuterium(D)-labelled organic compounds are used in many applications e.g., as therapeutic agents, internal standards in drug discovery and development, and new functional materials including dyes, catalysts, and light emitters. Conventionally, the synthesis of D-labelled compounds relies on (bio)catalysts due to their regio- and stereoselectivity, mild reaction conditions, and treatment of a broad scope of substrates. However, most (bio)catalysts are expensive to prepare/isolate, and some contain precious metals (PMs), e.g., Ir, Pd, whose markets are unpredictable, and which need to be separated from the products at great expense, post-reaction. With the general shift away from traditional ‘make-use-dispose’ approaches to ones that are less wasteful, the use of recyclable catalysts in both batch and continuous flow systems are increasingly employed. In this work, we comprehensively and critically review the catalysts and immobilization and recycling strategies implemented for the preparation of D-labelled organic compounds. Our aim is to highlight the most effective advances and expose the gaps in the literature to inform future research.
氘(D)标记的有机化合物用于许多应用,例如,作为治疗剂,药物发现和开发的内部标准,以及包括染料,催化剂和发光材料在内的新功能材料。传统上,d标记化合物的合成依赖于(生物)催化剂,因为它们具有区域和立体选择性、温和的反应条件和处理广泛的底物。然而,大多数(生物)催化剂的制备/分离成本很高,有些催化剂含有贵金属(pm),例如Ir, Pd,其市场不可预测,并且需要在反应后以高昂的费用从产品中分离出来。随着传统的“即用即弃”方法向更少浪费的方法的普遍转变,在批处理和连续流系统中越来越多地使用可回收催化剂。在这项工作中,我们全面和批判性地回顾了用于制备d标记有机化合物的催化剂、固定化和回收策略。我们的目标是突出最有效的进展,并揭示文献中的差距,为未来的研究提供信息。
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引用次数: 0
Light-induced perfluoroalkylative carbonylation of unactivated alkenes with a recyclable photocatalyst 利用可回收光催化剂对未活化烯烃进行光诱导全氟烷基羰基化反应
Pub Date : 2025-02-01 Epub Date: 2024-05-15 DOI: 10.1016/j.gresc.2024.05.002
Heng Yang , Shuyu Yang , Xiao-Feng Wu , Feng Chen
The development of heterogeneous catalysis difunctionalization of olefins is of great significance because it can save costs in the industry. Here, we report the perfluoroalkyl carbonylation reaction of inactive olefins catalyzed by titanium dioxide under light, obtaining β-perfluoroalkylamide compounds. The catalyst has high activity and wide functional group tolerance and can maintain high activity after multiple cycles. This catalyst reduces the use of precious metals, avoids ligands, and can easily be separated from the reaction mixtures.
烯烃多相催化双官能化的发展对节约工业成本具有重要意义。本文报道了二氧化钛在光照下催化无活性烯烃的全氟烷基羰基化反应,得到β-全氟烷基酰胺化合物。该催化剂具有高活性和宽官能团耐受性,多次循环后仍能保持高活性。这种催化剂减少了贵金属的使用,避免了配体,并且可以很容易地从反应混合物中分离出来。
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引用次数: 0
Sulfone as traceless activating group: Divergent synthesis of α-fluoroamides with C–F quaternary stereocenters 作为无迹激活基团的砜:含C-F季立体中心的α-氟酰胺的发散合成
Pub Date : 2025-02-01 Epub Date: 2024-10-05 DOI: 10.1016/j.gresc.2024.09.006
Jieqing Wu , Liying Fu , Renyi Diao , Longjun Nie , Chi Zhang , Yufeng Li , Chao Feng
A novel approach to α-fluoroamides bearing a C–F quaternary stereocenter is reported herein. With sulfone installed as the activating group, an alkyl group as well as a fluorine atom was introduced successively under mild conditions. Subsequently, heterolytic fission of the C–S bond occurred smoothly under photoredox conditions to afford a tertiary radical, which then engaged in varied intramolecular cyclizations depending on substrate structure and condition applied, rendering sulfone an overall traceless activating group.
本文报道了一种合成含C-F季立体中心α-氟酰胺的新方法。以砜为活化基团,在温和条件下依次引入烷基和氟原子。随后,C-S键在光氧化还原条件下顺利发生异裂变,产生三级自由基,然后根据底物结构和应用条件进行不同的分子内环化,使砜成为一个总体上不可见的激活基团。
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引用次数: 0
One-pot access to indazole fused-phenanthridinones via Rh(III)-catalyzed [4+2] annulation 通过Rh(III)催化[4+2]环法制备茚唑-菲并啶酮
Pub Date : 2025-02-01 Epub Date: 2023-09-29 DOI: 10.1016/j.gresc.2023.09.003
Shumin Li, Jinke Chang, Jian Shen, Xiuling Cui
An efficient synthesis of indazole fused phenanthridinones via Rh(III)-catalyzed inert C(sp2)-H activation/[4 ​+ ​2] annulation of 3-aryl-1H-indazoles with iodonium ylides has been developed, providing a strategy to access multi-conjugated π-system tetracyclic and pentacyclic aza-heterocyclics with the favorable photoluminescence properties. This “one-pot” reaction features high efficiency, excellent regioselectivity, a broad substrate compatibility and could be easily scaled up. Furthermore, the obtained products exhibited low toxicity in MDCK cells as well as selectively labeled the zebrafish larvae, which indicated that the titled products could be potentially utilized as biofluorescent probes or fluorescent dyes.
采用Rh(III)催化的惰性C(sp2)-H活化/[4 + 2]环法制备了3-芳基- 1h -吲哚酮类化合物,为获得具有良好光致发光性能的多共轭π系四环和五环偶氮杂环化合物提供了一条途径。这种“一锅式”反应具有效率高、区域选择性好、底物相容性广、易于扩大规模等特点。此外,所得产物对MDCK细胞具有低毒性,并且对斑马鱼幼虫具有选择性标记作用,表明该产物具有作为生物荧光探针或荧光染料的潜力。
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引用次数: 0
Advanced green synthesis: Solvent-free and catalyst-free reaction 先进的绿色合成:无溶剂、无催化剂反应
Pub Date : 2025-02-01 Epub Date: 2024-11-09 DOI: 10.1016/j.gresc.2024.11.001
Meng-Yao Li , Ao Gu , Jiatong Li , Yingbin Liu
The solvent-free and catalyst-free (SFCF) reaction has garnered significant interest among chemists due to its alignment with many of the 12 principles of green chemistry. In recent years, numerous innovative techniques have been employed to expand the scope of SFCF reactions and diversify the range of substrates. This paper presents an exhaustive examination of these transformations involving various functional groups, including alkenes, alkynes, aldehydes, ketones, imines, carboxylic acids, anhydrides, amides, amines, epoxides, aziridines, and organoselenides. Our review primarily seeks to elucidate the impact of solvent and concentration effects on these reactions by applying novel theories, such as the aggregate effect, multi-body effect, and multiple weak interactions, to ascertain how solvents impede these reactions. Additionally, different reaction mechanisms are contrasted under catalytic versus non-catalytic as well as solvent versus non-solvent conditions. Furthermore, the applications of such environmentally friendly reactions in fields such as material synthesis and drug synthesis are emphasized.
无溶剂无催化剂(SFCF)反应由于符合绿色化学12条原则中的许多原则而引起了化学家的极大兴趣。近年来,许多创新技术被用于扩大SFCF反应的范围和多样化的底物范围。本文提出了一个详尽的检查这些转化涉及各种官能团,包括烯烃,炔,醛,酮,亚胺,羧酸,酸酐,酰胺,胺,环氧化物,氮嘧啶和有机硒化物。我们的综述主要旨在通过应用新的理论,如聚集效应、多体效应和多重弱相互作用,阐明溶剂和浓度对这些反应的影响,以确定溶剂是如何阻碍这些反应的。此外,在催化与非催化以及溶剂与非溶剂条件下,对比了不同的反应机理。并着重介绍了这种环境友好反应在材料合成和药物合成等领域的应用。
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引用次数: 0
Visible-light-induced reusable decatungstate-photocatalyzed radical cascade alkylation/cyclization of isocyanides with simple alkanes, ethers and ketones 可见光诱导的可重复使用的十钨酸盐光催化自由基级联烷基化/异氰酸酯与简单烷烃、醚和酮的环化反应
Pub Date : 2025-02-01 Epub Date: 2024-01-06 DOI: 10.1016/j.gresc.2024.01.003
Ke-Li Wang, Hong-Tao Ji, Qiong-Hui Peng, Jun Jiang, Li-Juan Ou, Wei-Min He
With reusable sodium decatungstate (NaDT) as the photocatalyst, hydrocarbons (alkanes, ethers and ketones) as the alkylating agents, a wide range of alkylated fused N-heterocycles were obtained in high yield.
以可重复使用的癸钨酸钠(NaDT)为光催化剂,以碳氢化合物(烷烃、醚和酮)为烷化剂,高产率地获得了多种烷基化的融合 N-杂环。
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引用次数: 0
Development of a more efficient catalyst for the redox-neutral organocatalytic mitsunobu reaction by DFT-guided catalyst design 采用dft导向设计一种更高效的氧化还原-中性有机催化mitsunobu反应催化剂
Pub Date : 2024-11-01 Epub Date: 2023-11-13 DOI: 10.1016/j.gresc.2023.11.002
Dingguo Song , Changjun Zhang , Yuqi Cheng , Linlin Chen, Jie Lin, Changdi Zheng, Ting Liu, Yuxin Ding, Fei Ling, Weihui Zhong
The study of a Mitsunobu reaction is an important topic. Denton and co-workers first reported a novel (2-hydroxybenzyl)diphenylphosphine oxide for realizing the catalytic Mitsunobu reaction via a five-membered phosphonium species. However, it is still worth investigating how to improve catalysts with higher efficiency. Guided by computational and experimental studies, we designed a new type of biphenyl-based phosphine oxide that would form a six-membered phosphonium species as a key intermediate to trigger the catalytic Mitsunobu reaction with a lower barrier of the rate-determining step (30.3 ​kcal/mol). DFT calculations revealed that only trans dehydration was participated in our catalytic progress and a strong π-π interaction and small spatial constraint of TS-V were crucial for high behavior. This readily accessible, highly stable, easily recyclable and efficient catalyst would boost the catalytic Mitsunobu reaction.
光信反应的研究是一个重要的课题。Denton及其同事首次报道了一种新的(2-羟基苄基)二苯基氧化膦通过五元磷实现催化Mitsunobu反应。然而,如何提高催化剂的效率仍值得进一步研究。在计算和实验研究的指导下,我们设计了一种新型的基于联苯的氧化膦,它可以形成六元磷,作为催化Mitsunobu反应的关键中间体,具有较低的定速步垒(30.3 kcal/mol)。DFT计算表明,催化过程只涉及反式脱水,强π-π相互作用和TS-V的小空间约束是高行为的关键。这种易于获取、高度稳定、易于回收和高效的催化剂将促进催化光信反应。
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引用次数: 0
Pictet-spengler/transamination cascade reaction of indoles for modular synthesis of marinoquinoline analogues 喹啉类似物模块化合成中吲哚的Pictet-spengler/转氨化级联反应
Pub Date : 2024-11-01 Epub Date: 2023-09-20 DOI: 10.1016/j.gresc.2023.09.002
Jinjin Chen , Pingyu Jiang , Xinping Liu , Huawen Huang , Guojiang Mao , Guo-Jun Deng
The Pictet-Spengler/transamination cascade reaction enables modular synthesis of marinoquinoline analogues through three-component indole ring-expansion/cyclization in the manner of novel N1–C2 cleavage of indoles. This metal-free protocol exhibits very broad functional group tolerance with up to quantitative yields. Preliminary studies on the antitumor activity of the resultant marinoquinoline analogues reveal that the indolyl-attached pyrrolo[2,3-c]quinoline product (5d) shows great potential (IC50 of 0.32 ​μg/mL to HeLa cells) as a promising anticancer agent in clinic.
picet - spengler /转氨化级联反应以新颖的吲哚N1-C2裂解方式,通过三组分吲哚扩环/环化,模块化合成了氨基喹啉类似物。这种无金属方案具有非常广泛的官能团耐受性和定量产量。对所得的喹啉类似物抗肿瘤活性的初步研究表明,吲哚偶联吡咯[2,3-c]喹啉产物(5d)对HeLa细胞的IC50为0.32 μg/mL,具有广阔的临床应用前景。
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引用次数: 0
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Green Synthesis and Catalysis
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