Electrostatic Grafting of a Palladium N‐Heterocyclic Carbene Catalyst on a Periodic Mesoporous Organosilica and its Application in the Suzuki–Miyaura Reaction

Abstract

A periodic mesoporous organosilica material functionalized with a Pd N‐heterocyclic carbene complex was synthesized by applying an electrostatic grafting method. The resulting hybrid material was characterized by solid‐state 29Si and 13C cross‐polarization magic‐angle spinning NMR spectroscopy, XRD, thermogravimetric analysis, and BET measurements. The hybrid was applied as a catalyst for the Suzuki–Miyaura cross‐coupling between aryl chlorides and phenylboronic acid under heterogeneous and aerobic conditions. The supported catalyst exhibited excellent activity and stability and it could be reused at least six times without any loss of activity. Atomic absorption spectroscopy detected no Pd contamination in the products, and leaching tests verified that the reaction was truly heterogeneous.

Current advances in the utility of functionalized SBA mesoporous silica for developing encapsulated nanocatalysts: state of the art

“…Mesoporous silica materials [14][15][16][17][18][19][20] have not only proved their utilities as heterogeneous catalysts [21][22][23][24][25][26][27][28][29] for promoting various organic transformations, [30][31][32][33][34][35][36][37] but also nd interesting applications 38,39 in other research elds such as food chemistry, 40 production of bio-mass derived chemicals, [41][42][43][44][45] petrochemisry, 46-48 sensors, waste treatment, 49,50 optical materials and carriers. One of the most important advances in this eld is developing hybrid systems through functionalization of mesoporous silica materials.…”

Highly ordered Nanomaterial Functionalized Copper Schiff Base Framework: Synthesis, Characterization, and Hydrogen Peroxide Decomposition Performance

“…For these reasons, and taking into account our recent results related to the design of immobilized catalysts for organic transformations such as oxidation reactions and carbon-carbon bond formations [42][43][44], we report herein the synthesis of a novel Schiff base tridentate copper complex immobilized on mesoporous nanomaterials, Cu-L@SBA-15. The synthesized Cu-L@SBA-15 was characterized by techniques including transmission electron microscopy (TEM), Fourier transform infrared spectroscopy (FT-IR), cross polarization magic angle spinning (CP-MAS), 13-carbon nuclear magnetic resonance ( 13 C-NMR), X-ray powder diffraction spectrometry (PXRD), atomic absorption spectroscopy (AAS) and thermogravimetric analysis (TGA).…”

Reusable N-Heterocyclic Carbene Complex Catalysts and Beyond: A Perspective on Recycling Strategies

“…One year later, in 2015, Thiel and co-workers developed periodic mesoporous organosilica (PMO) immobilized NHC-Pd catalyst 249 via the electrostatic interaction strategy (Scheme ). The authors claimed that the electrostatic grafting method allowed the catalyst to interact more flexibly on the surface of the support compared with the covalent anchorage. The immobilized catalyst displayed a high activity in Suzuki coupling reactions under mild conditions.…”