A new functionalized mesoporous matrix supported Pd(ii)-Schiff base complex: an efficient catalyst for the Suzuki–Miyaura coupling reaction

Abstract

A new Pd(II) bounded 2D-hexagonally ordered functionalized MCM-41 type material (IV) has been synthesized. Functionalization was carried out by the anchoring of 3-aminopropyltriethoxysilane in the MCM-41 type mesoporous material, followed by grafting with 2,6-diacetylpyridine (DAP) to give a N3-type Schiff base chelating attachment for the Pd(II) species. Fourier transform infrared (FTIR), powder X-ray diffraction (PXRD) and high resolution transmission electron microscopy (HRTEM) studies have been used to characterize the material. Material IV behaves as a highly active catalyst towards Suzuki-Miyaura cross-coupling reaction for the synthesis of biaryl organics. In addition, IV acts as a true heterogeneous catalyst in coupling reaction. It was found that this catalyst is highly efficient and recyclable towards Suzuki-Miyaura reaction with high turn over frequencies. X-Ray photoelectron spectroscopic (XPS) analysis was employed to understand the oxidation state of the palladium atom in the catalyst (IV) and its loading in the material.

Palladium immobilized in the nanocages of SBA-16: An efficient and recyclable catalyst for Suzuki coupling reaction

“…Details on the synthesis and characterization of these materials are given elsewhere [34]. This solid was then refluxed with 10 g p-bromoacetophenone (50 mmol) in methanol for 3 h at 60°C [35]. The resulting yellowish solid PBA-Fe 3 O 4 @SiO 2 was then collected by filtration and was dried in a desiccator (Scheme 2).…”

“…To elucidate this matter, we have performed hot filtration test [50] and three-phase test [5,35,[51][52][53] as described below.…”

Functionalized mesoporous materials as efficient organocatalysts for the syntheses of xanthenes

“…In this context functionalized mesoporous silicas can be very promising support due to their exceptionally high surface area, tunable nanoscale pores and wide range of compositional variations [10][11][12][13][14][15]. Design and synthesis of surface functionalized ordered mesoporous silica materials have attracted particular attention for their application in catalysis [16][17][18][19], adsorption [20,21], ion-exchange [22], sensing [23] and so on. Rational design of these materials using suitable organic functionalities give rise to smart mesoporous materials [24], which can have potential applications in many other frontier areas of science.…”

PEG Modification Effect of Silica on the Suzuki–Miyaura Coupling Reaction Using Silica-immobilized Palladium Catalysts

“…A number of studies about the design and preparation of immobilized catalysts for the Suzuki-Miyaura reaction have been reported [15][16][17][18][19][20][21]. Since the reaction takes place in aqueous organic media, modifying supports with amphiphilic polymers such as polyethylene glycol (PEG) effectively promotes the reaction.…”