Ordered mesoporous SBA‐15/PrSO₃Pd and SBA‐15/PrSO₃Pd_NP as active, reusable and selective phosphine‐free catalysts in CX activation Heck coupling process

Abstract

The incorporation of sulfonate into mesoporous SBA‐15 molecular sieves as ligands for palladium ions was used. Then SBA‐15/PrSO3Pd and SBA‐15/PrSO3PdNP were prepared and applied for the Heck arylation reaction of conjugate alkenes with aryl halides, to afford corresponding cross‐coupling products under phosphine‐free aerobic conditions with good to excellent yields. These supported palladium pre‐catalysts could be separated easily from reaction products and reused several times, showing superiority over homogeneous catalysts for industrial and chemical applications. Copyright © 2015 John Wiley & Sons, Ltd.

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

“…123 Low Pd loading, reusability of the catalyst and high yields were the advantageous of that protocol.…”

Applications of SBA-15 supported Pd metal catalysts as nanoreactors in C–C coupling reactions

“…Hot ltration test for the catalyst in middle of the reactions demonstrated a minor of Pd leaching. 131 Catalyst Pd@thiazolidine-modied SBA-15 (38) discussed earlier in the Suzuki reaction, proved also to be a highly efficient and stable catalyst in the Heck coupling between aryl iodides and methyl acrylate or styrenes with a similar amount of Pd loading (Scheme 99). Yields of alkene products were excellent or high, except in the reaction of methyl acrylate and 2- iodothiophene.…”

“…130 SBA-15/PrSO 3 H-Pd-NPs (40) catalyst, as described above synthesized by Rostamnia et al, also investigated for the Heck arylation reaction of aryl halides with conjugate alkenes, to yield corresponding unsymmetric biaryls in high to excellent yields under phosphine-free aerobic conditions (Scheme 98). 131 This heterogeneous catalyst could be separated easily from reaction mixture and reused several times, displaying superiority over homogeneous catalysts for chemical and industrial applications. Hot ltration test for the catalyst in middle of the reactions demonstrated a minor of Pd leaching.…”

Extended architectures constructed of thiourea‐modified SBA‐15 nanoreactor: A versatile new support for the fabrication of palladium pre‐catalyst

“…Palladium nanoparticles (Pd NPs) have been immobilized on a wide range of solid materials and have been applied as efficient catalysts for many reactions such as cross‐coupling, domino reactions, dehydrogenation/hydrogenation, oxidation and reduction, and others. Among carbon–carbon coupling reactions, the Suzuki and Heck reactions due to mild reaction conditions, insensitivity to moisture, tolerance of active functional groups and low toxicity are the most explored examples . Numerous investigations have indicated that supports with functional groups such as amines, imines, thiols, phosphine and sulfonic acids could be anchored on the surface of silica materials and then interacted with Pd NPs for use in coupling reactions.…”