Bibliographies thématiques / Catalysis, gold, cascade reactions, cyclisations

Littérature scientifique sur le sujet « Catalysis, gold, cascade reactions, cyclisations »

Auteur : Grafiati

Publié le 10 mars 2023

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Articles de revues sur le sujet "Catalysis, gold, cascade reactions, cyclisations"

Zhang, Yun, Tuoping Luo et Zhen Yang. « Strategic innovation in the total synthesis of complex natural products using gold catalysis ». Nat. Prod. Rep. 31, n^o 4 (2014) : 489–503. http://dx.doi.org/10.1039/c3np70075e.

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This review has been organized from the perspective of synthetic target families, with emphasis on the use of gold-catalyzed transformations and cascade reactions that significantly increase molecular complexity.

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Ikeuchi, Takaya, Shinsuke Inuki, Shinya Oishi et Hiroaki Ohno. « Gold(I)‐Catalyzed Cascade Cyclization Reactions of Allenynes for the Synthesis of Fused Cyclopropanes and Acenaphthenes ». Angewandte Chemie International Edition 58, n^o 23 (3 juin 2019) : 7792–96. http://dx.doi.org/10.1002/anie.201903384.

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Cadierno, Victorio. « Gold-Catalyzed Addition of Carboxylic Acids to Alkynes and Allenes : Valuable Tools for Organic Synthesis ». Catalysts 10, n^o 10 (18 octobre 2020) : 1206. http://dx.doi.org/10.3390/catal10101206.

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In this contribution, the application of gold-based catalysts in the hydrofunctionalization reactions of alkynes and allenes with carboxylic acids is comprehensively reviewed. Both intra- and intermolecular processes, leading respectively to lactones and linear unsaturated esters, are covered. In addition, cascade transformations involving the initial cycloisomerization of an alkynoic acid are also discussed.

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Herrero, María Teresa, Jokin Díaz de Sarralde, Nerea Conde, Aitor Herrán, Garazi Urgoitia et Raul SanMartin. « Metal-Catalyzed Cascade Reactions between Alkynoic Acids and Dinucleophiles : A Review ». Catalysts 13, n^o 3 (28 février 2023) : 495. http://dx.doi.org/10.3390/catal13030495.

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Cascade reactions provide a straightforward access to many valuable compounds and reduce considerably the number of steps of a synthetic sequence. Among the domino and multicomponent processes that involve alkynes, the cascade reaction between alkynoic acids and C-, N-, O- and S-aminonucleophiles stands out as a particularly powerful tool for the one-pot construction of libraries of nitrogen-containing heterocyclic compounds with scaffold diversity and molecular complexity. This reaction, based on an initial metal-catalyzed cycloisomerization that generates an alkylidene lactone intermediate, was originally catalyzed by gold(I) catalysts, along with silver salts or Brönsted acid additives, but other alternative metal catalysts have emerged in the last decade as well as different reaction media. This review examines the existing literature on the topic of metal-catalyzed cascade reactions of acetylenic acids and dinucleophiles and discusses aspects concerning substrate/catalyst ratio for every catalyst system, nature of the aminonucleophile involved and substrate scope. In addition, alternative solvents are also considered, and an insight into the pathway of the reaction and possible intermediates is also provided.

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Buonerba, Antonio, et Alfonso Grassi. « Trends in Sustainable Synthesis of Organics by Gold Nanoparticles Embedded in Polymer Matrices ». Catalysts 11, n^o 6 (7 juin 2021) : 714. http://dx.doi.org/10.3390/catal11060714.

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Gold nanoparticles (AuNPs) have emerged in recent decades as attractive and selective catalysts for sustainable organic synthesis. Nanostructured gold is indeed environmentally friendly and benign for human health; at the same time, it is active, under different morphologies, in a large variety of oxidation and reduction reactions of interest for the chemical industry. To stabilize the AuNPs and optimize the chemical environment of the catalytic sites, a wide library of natural and synthetic polymers has been proposed. This review describes the main routes for the preparation of AuNPs supported/embedded in synthetic organic polymers and compares the performances of these catalysts with those of the most popular AuNPs supported onto inorganic materials applied in hydrogenation and oxidation reactions. Some examples of cascade coupling reactions are also discussed where the polymer-supported AuNPs allow for the attainment of remarkable activity and selectivity.

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Jia, Xiuwen, Pinyi Li, Xiaoyan Liu, Jiafu Lin, Yiwen Chu, Jinhai Yu, Jiang Wang, Hong Liu et Fei Zhao. « Green and Facile Assembly of Diverse Fused N-Heterocycles Using Gold-Catalyzed Cascade Reactions in Water ». Molecules 24, n^o 5 (11 mars 2019) : 988. http://dx.doi.org/10.3390/molecules24050988.

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The present study describes an AuPPh3Cl/AgSbF6-catalyzed cascade reaction between amine nucleophiles and alkynoic acids in water. This process proceeds in high step economy with water as the sole coproduct, and leads to the generation of two rings, together with the formation of three new bonds in a single operation. This green cascade process exhibits valuable features such as low catalyst loading, good to excellent yields, high efficiency in bond formation, excellent selectivity, great tolerance of functional groups, and extraordinarily broad substrate scope. In addition, this is the first example of the generation of an indole/thiophene/pyrrole/pyridine/naphthalene/benzene-fused N-heterocycle library through gold catalysis in water from readily available materials. Notably, the discovery of antibacterial molecules from this library demonstrates its high quality and potential for the identification of active pharmaceutical ingredients.

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Neupane, Pratik, Likai Xia et Yong Rok Lee. « One-Pot Synthesis of Multi-Substituted 4-Pyrones by a Gold- Catalyzed Cascade of Wolff Rearrangement/[4+2] Cycloaddition/ Elimination Reactions ». Advanced Synthesis & ; Catalysis 356, n^o 11-12 (20 juin 2014) : 2566–74. http://dx.doi.org/10.1002/adsc.201301086.

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Liu, Yuanhong, Feijie Song et Shenghai Guo. « Cleavage of a Carbon−Carbon Triple Bond via Gold-Catalyzed Cascade Cyclization/Oxidative Cleavage Reactions of (Z)-Enynols with Molecular Oxygen ». Journal of the American Chemical Society 128, n^o 35 (septembre 2006) : 11332–33. http://dx.doi.org/10.1021/ja062610q.

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Lu, Yuhua, Xiangwei Du, Xueshun Jia et Yuanhong Liu. « Gold-Catalyzed Intermolecular Reactions of (Z)-Enynols with Indoles for the Construction of Dihydrocyclohepta[b]indole Skeletons through a Cascade Friedel-Crafts/Hydroarylation Sequence ». Advanced Synthesis & ; Catalysis 351, n^o 10 (juillet 2009) : 1517–22. http://dx.doi.org/10.1002/adsc.200900068.

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Komatsu, Tomohiro, Kazuki Hishii, Michiko Kimura, Satoshi Amaya, Hiroaki Sakamoto, Eiichiro Takamura, Takenori Satomura et Shin-ichiro Suye. « Highly Efficient Multi-Step Oxidation Bioanode Using Microfluidic Channels ». International Journal of Molecular Sciences 22, n^o 24 (16 décembre 2021) : 13503. http://dx.doi.org/10.3390/ijms222413503.

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With the rapid decline of fossil fuels, various types of biofuel cells (BFCs) are being developed as an alternative energy source. BFCs based on multi-enzyme cascade reactions are utilized to extract more electrons from substrates. Thus, more power density is obtained from a single molucule of substrate. In the present study, a bioanode that could extract six electrons from a single molecule of L-proline via a three-enzyme cascade reaction was developed and investigated for its possible use in BFCs. These enzymes were immobilized on the electrode to ensure highly efficient electron transfer. Then, oriented immobilization of enzymes was achieved using two types of self-assembled monolayers (SAMs). In addition, a microfluidic system was incorporated to achieve efficient electron transfer. The microfluidic system, in which the electrodes were arranged in a tooth-shaped comb, allowed for substrates to be supplied continuously to the cascade, which resulted in smooth electron transfer. Finally, we developed a high-performance bioanode which resulted in the accumulation of higher current density compared to that of a gold disc electrode (205.8 μA cm−2: approximately 187 times higher). This presents an opportunity for using the bioanode to develop high-performance BFCs in the future.

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Thèses sur le sujet "Catalysis, gold, cascade reactions, cyclisations"

Pertschi, Romain. « Elaboration d'hétérocycles complexes par ammoniumation catalysée à l'or(I) ». Thesis, Strasbourg, 2019. http://www.theses.fr/2019STRAF036.

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Les hétérocycles azotés ont toujours retenu l’attention des chimistes du fait de leurs potentielles activités biologiques mais également pour leurs grandes occurrences dans les produits naturels. De ce fait émerge la nécessité de développer de nouvelles méthodes de synthèse innovantes permettant un accès rapide et efficace à ces hétérocycles. C’est dans cette philosophie que s’inscrivent ces travaux de thèse dont l’objectif est le développement de nouvelles approches basées sur l’utilisation de réactions d’ammoniumation catalysées à l’or(I) afin d’induire des cascades réactionnelles donnant accès à une large variété d’hétérocycles azotés. Ainsi, un motif de base N-sulfonyl-2-(1-propargyl)azétidine a permis d’accéder à une large variété de dérivés pyrroliques et de tétrahydroazépines. L’extension du concept d’ammoniumation lors de l’utilisation des N-(2-alcynylaryl)sulfonyl azétidines a conduit à l’obtention de benzosultames. Un autre défi majeur de la chimie de synthèse moderne est l’obtention de molécules énantiopures. Pour répondre à cette problématique, de nouveaux complexes chiraux NHC platine(II) ont été synthétisés et évalués en tant que catalyseurs sur des réactions de cycloisomérisation
Nitrogen-containing heterocycles have always retained the attention of chemists considering their potent biological properties as well as their large occurrence in natural product structures. Therefore, the development of new innovative synthetic methods that allow a rapid and efficient access to these heterocycles is highly sought. It is in this philosophy that these PhD works take place, whose aims at the development of new approaches based on gold(I) catalyzed ammoniumation reactions in order to trigger cascade reactions and to reach important nitrogen-containing heterocycles. The N-sulfonyl-2-(1-propargyl) azetidine scaffold allows formation of a large variety of pyrroles and tetrahydroazepines derivatives. The extension of the concept of ammoniumation by using N-(2-alcynylaryl)sulfonyl azetidines allowed the formation of benzosultam derivatives. Another major challenge of modern synthetic chemistry is the formation of enantiopur molecules. To reach this goal, new chiral NHC platinum (II) complexes have been synthesized and evaluated as catalysts for cycloisomerization reactions

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Rinaldi, Antonia. « New gold(I)-catalysed cascade reactions for the synthesis of pentannulated N-hetero- and carbacycles ». Doctoral thesis, 2021. http://hdl.handle.net/2158/1235835.

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This thesis work aims at the development of new gold(I)-catalysed tandem processes for the synthesis of pentannulated N-hetero- and carbacycles in a highly efficient manner. The general approach entails an initial Claisen rearrangement, through which an allene-gold(I) complex is formed as intermediate, and a final cyclisation of the latter. Depending on the substrate, different catalysts have been evaluated in order to promote the second step of the tandem process. While with carba- and N-heterocycles the reaction occurs with most of phosphine and carbene ligands (chapter 3), when using aromatic substrates only a carbene ligand (IPr) turned out to be efficient for the final cyclisation (chapter 5). This tandem process was further implemented by adding another step to the cascade. In fact, the pentannulated products were in situ elaborated through Grignard, Wittig and Diels-Alder reactions (chapter 4), exploiting the aldehyde functionality and/or the diene system. In this way, we performed at least three reactions in one-pot, achieving the synthesis of complex compounds under mild conditions, in short times and with good to excellent yields. This approach was then applied to the total synthesis of a target compound, epi-Jungianol (Chapter 6). By employing the presented methodologies, two almost equivalent routes were accomplished, thus demonstrating the usefulness of our tandem process. Finally, during a secondment activity in the group of Prof. A. M. Echavarren at the Catalan Institute of Chemical Investigation (ICIQ), the design and the synthesis of new gold(I) cavitand catalysts were studied (chapter 7). Moreover, the activity of some resorcinarene-based gold(I) catalysts was investigated through alkoxycyclisations of dienynes, obtaining promising results.

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Chapitres de livres sur le sujet "Catalysis, gold, cascade reactions, cyclisations"

Liu, Rai-Shung. « GOLD CATALYSIS ON TANDEM AND CASCADE REACTIONS ». Dans Catalytic Science Series, 253–74. IMPERIAL COLLEGE PRESS, 2014. http://dx.doi.org/10.1142/9781848168534_0007.

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