Silica–acetylacetone‐supported palladium nanoparticles as an efficient and reusable catalyst in the Heck–Mizoroki C–C cross‐coupling reaction

Abstract

The preparation of palladium nanoparticles supported on acetylacetone‐modified silica gel and their catalytic application for Heck olefination of aryl halides were investigated. The catalyst was characterized using X‐ray diffraction, X‐ray photoelectron spectroscopy, and transmission and scanning electron microscopies. The supported palladium nanoparticles are demonstrated to be a highly active and reusable catalyst for the Heck reaction. Several reaction parameters, including type and amount of solvent and base, were evaluated. The heterogeneity of the catalytic system was investigated with results indicating that there is a slight palladium leaching into the reaction solution under the applied reaction conditions. Despite this metal leaching, the catalyst can be reused nine times without significant loss of catalytic activity. Copyright © 2015 John Wiley & Sons, Ltd.

Organoselenium ligands for heterogeneous and nanocatalytic systems: development and applications

“…56 One such preformed molecular complex, reported by Yao and co-workers in 2004, 56 is an outstanding homogeneous catalyst for this reaction and shows extremely high efficiency. H6 catalyses the reaction in a shorter reaction time (45 minutes to 6 hours) (Scheme 24) than many other heterogeneous catalysts developed by immobilizing palladium on solid supports such as silica, 115 boron nitride, 116 La 2 O 3 , 117 and carbon nanocoils. 118 These catalytic systems require a longer reaction time (3-24 hours) [114][115][116][117] and high catalyst loading.…”

Application of Curcumin as Ligand in [Pd(Curc‐H)2] Catalyst for Carbon‐Carbon Bond Formation in Heck and Suzuki Coupling Reactions

“…al have reported efficiency of Pd(acac) 2 nanocluster for Suzuki reaction between aryl bromides or chlorides and boronic acids with high yield and also showed that it has an efficient catalytic activity for Heck reaction of aryl bromides with styrene . Whereas Hajipour demonstrated the silica–acetylacetone‐supported palladium nanoparticles for Heck reaction …”

Immobilized Pd on (S)‐methyl histidinate‐modified multi‐walled carbon nanotubes: a powerful and recyclable catalyst for Mizoroki–Heck and Suzuki–Miyaura C–C cross‐coupling reactions in green solvents and under mild conditions

“…[49][50][51][52][53][54][55][56] In addition, MWCNTs can be used as very good catalyst supports because of their high surface area and insolubility in most solvents. [57][58][59][60][61][62][63] In continuation of our recent investigations of the application of heterogeneous catalytic systems in cross-coupling reactions, [64][65][66][67] in the work reported here, palladium was immobilized on methyl histidinate-modified MWCNTs and the catalytic activity was demonstrated by employing the Mizoroki-Heck and Suzuki-Miyaura coupling reactions. Our catalytic system results in the desired products in faster reaction times, at lower temperatures using greener solvents in comparison with conventional methods.…”