Reusable Catalysts for Copper‐Mediated Cross‐Coupling Reactions under Heterogeneous Conditions

Wang, Zhiyong; Wan, Changfeng; Wang, Ye

doi:10.1002/9781118690659.ch20

Cited by 5 publications

(2 citation statements)

References 107 publications

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“…Cu-catalyzed C–S bond formation is a flexible synthetic tool that is in high demand in research and industrial fields. A simple protocol allows the coupling of an impressive variety of S-nucleophiles with functionalized aryl and alkyl halides including hindered, electron-poor, electron-rich, and heterocyclic compounds. − The key advantages of copper-based catalytic systems are (i) the commercial availability and relatively low toxicity of copper species; (ii) the high catalytic activity; and (iii) the possibility to carry out reactions under ligand-free conditions, often with the use of nontoxic solvents or recyclable ionic liquids. − In some cases, Cu-mediated transformations may be superior to the well-known Pd-catalyzed reactions …”

Section: Introductionmentioning

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: Introductionmentioning

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 carbon-heteroatom bond formation by the Cu-catalyzed cross-coupling reactions of aryl halides with sulphurcontaining nucleophiles is a powerful tool in organic synthetic reactions. [102][103][104][105][106] However, the metal NP mediated C-S bond formation reaction received less attention. 107 These C-S substrates are key building blocks in the field of total organic synthesis, biochemistry, solar cells or other functional materials, pharmaceutical, agrochemical, polymer, dye industries, and large-scale production of fine chemicals.…”

Section: C-s Bond Formationmentioning

confidence: 99%