Abstract
Copper nanoparticles on different supports are effective reusable catalysts for the palladium- and ligand-free coupling of aryl halides with alkynes, thiols and azoles.
Highlights
Immobilised copper nanoparticles obtained by various methods and on different supports have been demonstrated to be versatile and reusable catalysts for a wide range of reactions, including cross-coupling reactions forming carbon–carbon and carbon–heteroatom bonds (C–N, C–O, C–S, C–P),[4,7] oxidative coupling reactions,[8] as well as multicomponent reactions.[9]In this work, we set out a broad synthetic application of some copper-based nanocatalysts supported on four different materials: a carbonaceous material,[10] a ceramic metal oxide,[11] a clay mineral[12] and a microporous zeolite.[13]
The full characterisation of copper nanoparticles on activated carbon (CuNPs/C)9b and copper nanoparticles on zeolite Y (CuNPs/ZY)8b was already reported in the literature
The copper nanoparticles on titania (CuNPs/ TiO2) and copper nanoparticles on montmorillonite (CuNPs/ MK-10)12b were characterised by means of transmission electron microscopy (TEM), energy-dispersive X-ray spectroscopy (EDX) and X-ray photoelectron spectroscopy (XPS)
Summary
Immobilised copper nanoparticles obtained by various methods and on different supports have been demonstrated to be versatile and reusable catalysts for a wide range of reactions, including cross-coupling reactions forming carbon–carbon and carbon–heteroatom bonds (C–N, C–O, C–S, C–P),[4,7] oxidative coupling reactions,[8] as well as multicomponent reactions.[9]In this work, we set out a broad synthetic application of some copper-based nanocatalysts supported on four different materials: a carbonaceous material (activated carbon),[10] a ceramic metal oxide (nanosized titania),[11] a clay mineral (montmorillonite-K10)[12] and a microporous zeolite (sodium Y zeolite).[13]. The most active catalyst (CuNPs/ZY) was deployed in the coupling reaction of phenylacetylene with different aryl halides at a ca. (4a) catalysed by CuNPs on different supports; 1c (0.25 mmol), 4a (1.5 equiv.), catalyst (1 mol% Cu), K2CO3 (2 equiv.), DMF (1 mL), 80 °C, Ar; yield of 5ca determined by 1H NMR.
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