CuO hollow nanosphere-catalyzed cross-coupling of aryl iodides with thiols

Woo, Hyunje; Mohan, Balaji; Heo, Eunjung; Park, Kang Hyun; Song, Hyunjoon

doi:10.1186/1556-276x-8-390

Cited by 18 publications

(13 citation statements)

References 38 publications

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“…Typically, 5−20 mol % of copper catalyst is employed in similar reactions, and efficient synthetic applications with <5 mol % of the catalyst are rare. [4][5][6][7][8][9][10][11][12][16][17][18][19]34 Based on the experimental results, a plausible mechanism for the C−S cross-coupling reaction, with copper oxides as the catalyst precursor, can be proposed (Scheme 3).…”

Section: Acs Catalysismentioning

confidence: 99%

Nature of the Copper-Oxide-Mediated C–S Cross-Coupling Reaction: Leaching of Catalytically Active Species from the Metal Oxide Surface

et al. 2016

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Copper-oxide-catalyzed cross-coupling reaction is a well-known strategy in heterogeneous catalysis. A large number of applications have been developed, and catalytic cycles have been proposed based on the involvement of the copper oxide surface. In the present work, we have demonstrated that copper(I) and copper(II) oxides served as precursors in the coupling reaction between thiols and aryl halides, while catalytically active species were formed upon unusual leaching from the oxide surface. A powerful cryo-SEM technique has been utilized to characterize the solution-state catalytic system by electron microscopy. A series of different experimental methods were used to reveal the key role of copper thiolate intermediates in the studied catalytic reaction. The present study shows an example of leaching from a metal oxide surface, where the leaching process involved the formation of a metal thiolate and the release of water. A new synthetic approach was developed, and many functionalized sulfides were synthesized with yields of up to 96%, using the copper thiolate catalyst. The study suggests that metal oxides may not act as an innocent material under reaction conditions; rather, they may represent a source of reactive species for solution-state homogeneous catalysis.

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Section: Acs Catalysismentioning

confidence: 99%

Nature of the Copper-Oxide-Mediated C–S Cross-Coupling Reaction: Leaching of Catalytically Active Species from the Metal Oxide Surface

et al. 2016

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“…The optimization of reaction conditions for a chemical reaction to avoid the excess reagents and solvents using nanomaterials as recyclable catalysts is considered to be a challenging task to achieve the aforementioned goal. − Hierarchically porous metal oxides consisting of building blocks in multiple length scales have attracted significant attention due to their unique properties to achieve sustainable applications in various fields including photocatalysis, photonic devices, chemical sensors, energy conversion and storage systems, and drug delivery. − However, the catalytic potential of these hierarchically porous metal oxides has not been well studied in organic synthesis. Copper oxide is one such metal oxide that has found potential applications in various fields including catalysis. − However, there are very limited methods for the synthesis of hierarchically porous copper oxide nanostructures to explore their wide range of applications in science and technology. − To the best of our knowledge, the catalytic potential of hierarchically porous copper oxide has not been studied for the synthesis of pharmacologically active heterocycles under green reaction conditions. Benzofuran(s) are such important O-heterocyclic scaffolds found in various natural products and pharmaceuticals with a wide range of biological activities such as anticancer, antioxidative, and anti-inflammatory properties (Figure ).…”

Section: Introductionmentioning

confidence: 99%

Hierarchically Porous Sphere-Like Copper Oxide (HS-CuO) Nanocatalyzed Synthesis of Benzofuran Isomers with Anomalous Selectivity and Their Ideal Green Chemistry Metrics

Purohit

Rajesh

Rawat

2017

ACS Sustainable Chem. Eng.

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Development of nanocatalysts for a chemical reaction with ideal values in green chemistry metrics is considered to be a challenging task to achieve sustainable chemistry. With this aim, we herein report a hierarchically porous sphere-like copper oxide (HS-CuO) nanocatalyst to afford benzofuranamine and dihydro-benzofuranamine isomers with anomalous selectivity via O-annulated A3 coupling among salicylaldehydes, secondary amines, and alkynes followed by cycloisomerization in the absence of base and solvent. The anomalous selectivity of benzofuran isomers was dependent on the electronic factors of substituents on salicylaldehyde and the type of secondary amines used in the coupling reaction. The HS-CuO nanocatalyst was recycled five times without significant loss in its catalytic activity. The present method offers several advantages over the reported methods such as wide substrate scope with anomalous selectivity in the products, high yields in short reaction time, avoided the usage of extra reagents such as additives/bases, and showed ideal values of green chemistry metrics such as low E-factor and process mass intensity (PMI), high atom economy (AE), reaction mass efficiency (RME), and carbon efficiency (CE).

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“…8). Acetylene black (CuO/AB) was used to overcome the problems but till the low conversion of the reaction was observed but high selectivity among the products has been observed (Woo et al 2013).…”

Section: Carbon-carbon Coupling Reactionsmentioning

confidence: 99%

Recent developments of supported and magnetic nanocatalysts for organic transformations: an up-to-date review

Gebre

2021

Appl Nanosci

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Designing and building an ideal catalyst for organic reactions is needed to increase the efficiency, reaction conditions, and to reduce its environmental impacts. The growth of nanotechnology is realized in the production of various nano-level catalysts for different applications. The as-synthesized nanocatalysts are easily manipulated to a desired shape and size with a high surface area to volume ratio, which is their critical property of the interaction of the nanomaterials with the substrates. These days, a vast array of catalysts (nanocatalysts) such as metals, metal oxides, magnetic, and alloyed/mixed nanocatalysts are applied in organic reactions to synthesize important chemicals in industries and pharmaceutical sectors with a high yield, selectivity, and reusability via reduction/hydrogenation, oxidation, condensation, C-C coupling, cyclization, and more. Consequently, this present review highlights the application of various nanocatalysts in organic reactions by combining certain proposed reaction mechanisms that have shown the impact of nanoparticles on the reactions. The factors influencing nanocatalyst performances are also discussed. Finally, the conclusion and future prospects are conveyed.

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CuO hollow nanosphere-catalyzed cross-coupling of aryl iodides with thiols

Cited by 18 publications

References 38 publications

Nature of the Copper-Oxide-Mediated C–S Cross-Coupling Reaction: Leaching of Catalytically Active Species from the Metal Oxide Surface

Nature of the Copper-Oxide-Mediated C–S Cross-Coupling Reaction: Leaching of Catalytically Active Species from the Metal Oxide Surface

Hierarchically Porous Sphere-Like Copper Oxide (HS-CuO) Nanocatalyzed Synthesis of Benzofuran Isomers with Anomalous Selectivity and Their Ideal Green Chemistry Metrics

Recent developments of supported and magnetic nanocatalysts for organic transformations: an up-to-date review

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