Highly Crystallized Pd/Cu Nanoparticles on Activated Carbon: An Efficient Heterogeneous Catalyst for Sonogashira Cross-Coupling Reaction

Abstract

In the quest for efficient and recyclable heterogeneous catalysts for Sonogashira coupling reactions, a PEG-OMe (Methoxy Polyene Glycol) - mediated method was developed to immobilize Pd/Cu bimetallic nanoparticles on activated carbon (AC). Catalytic experiments showed that Pd/Cu@AC prepared in a PEG-OMe 500 had the highest activity. The morphology and composition of the catalyst were determined, and the identified crystallized and heterometallic nanoparticles of Pd/Cu were essential for an efficient catalytic cycle. The Pd/Cu@AC catalyst was successfully used in Sonogashira reactions (21 examples) including with aryl bromides as the coupling partner in EtOH at 80–100 °C. The catalyst was recycled at least nine times.

Palladium Supported on Porous Organic Polymer as Heterogeneous and Recyclable Catalyst for Cross Coupling Reaction

“…The cross-coupling reaction is one of the most important methods for the direct synthesis of related products [ 6 ]. In the past decades, a wide range of coupling reactions has been catalyzed effectively by palladium catalysts to form the carbon–carbon bond [ 7 , 8 , 9 , 10 , 11 , 12 , 13 ]. In order to reduce the reaction cost and expand the catalytic application, several metals have displayed analogous catalytic ability in this transformation [ 14 ].…”

BNPs@SiO2(CH2)3 -TAPC-O-(CH2)2NH2-Pd (0) as a Nanocatalyst for the Coupling Reactions and Removing of Organic Dyes

“…One of the most effective and practical ways to overcome these problems is the heterogenization of homogeneous catalysts and the use of solid substrates 7 . Also, nanotechnology enables synthesis of nanostructured-scale heterogeneous catalysts that have large active surfaces due to their small size and are easily recovered from the reaction medium that is very environmentally and economically desirable [9][10][11][12][13] . Furthermore, the use of electron rich ligands, bulky enough, environmentally friendly, inexpensive and easily available ligands in coordination chemistry is one of the attractive issues 14,15 .…”

Biomass Waste-Derived Pd–PiNe Catalyst for the Continuous-Flow Copper-Free Sonogashira Reaction in a CPME–Water Azeotropic Mixture

“…Specifically, in the Sonogashira cross-coupling, a mixture of an organic solvent and water is used as it allows the solubilization of the halide salts stoichiometrically produced in the process. However, these mixtures cannot be easily recovered leading to additional complicated issues arising from the disposal of hazardous waste. − …”