Palladium nanoparticles supported on agarose‐catalyzed Heck–Matsuda and Suzuki–Miyaura coupling reactions using aryl diazonium salts

Abstract

In this article, palladium nanoparticles supported on agarose were used as an efficient catalyst for Heck-Matsuda and Suzuki-Miyaura coupling reactions of structurally different aryldiazonium tetrafluoroborate substrates in aqueous media. Heck-Matsuda reactions proceeded at 40 C whereas Suzuki-Miyaura reactions were carried out at room temperature. Both reactions required low catalyst loading. The catalyst was also recycled for the model reaction for three runs.

ChemInform Abstract: Heterogeneous Palladium Catalysts for Suzuki—Miyaura Coupling Reactions Involving Aryl Diazonium Salts

“…Gholinejad described another palladium catalyst supported on an atural polymer with the synthesis of agarose-supported palladium nanoparticles. [21] Agarose is an atural abundant linear polymer constituted of repeated 1,3-linked b-d-galactopyranose and 1,4-linked 3,6-anhydro-a-l-galactopyranose units (Figure 4). Agarosei sc onsidered as ag reen support as it can be easily biodegraded.…”

Cross‐Coupling Arylations: Precedents and Rapid HistoricalReview of the Field

“…In 2012, Gholinejad reported the Heck-Matsuda reaction (as well as the Suzuki-Miyaura reaction) using palladium nanoparticles [97]. The nanoparticles were supported on agarose beads, and at a loading of 2.6 μmol a variety of aryl diazonium tetrafluoroborate salts could be coupled with a variety of alkenes at 40 ∘ C. Water was shown to be the best solvent and yields of over 80% were achieved.…”

“…The supported palladium nanoparticle catalyst is prepared by adding Pd(OAc) 2 (0.022 g, 1 mmol) to a solution of agarose (1 g) in water (100 ml) and then adding this solution to a aqueous acid solution (100 ml, with the pH fixed to 4 by adding HCl) and stirring at 80 ∘ C [97]. An aqueous solution of citric acid (4 mmol in 20 ml H 2 O) is added dropwise.…”

Silver nanoparticles supported on ionic‐tagged magnetic hydroxyapatite as a highly efficient and reusable nanocatalyst for hydrogenation of nitroarenes in water

“…Therefore, there have been many efforts to fabricate heterogeneous catalysts in which metal NPs are immobilized on various kinds of solid support such as organic polymers, silica, zeolite, alumina, graphite oxide and magnetic NPs. Moreover, the relatively high surface area and appropriate pore size of inorganic supports maintain their competitive advantages over others . Hydroxyapatite is a potentially useful material for designing new functionalized heterogeneous catalysts, because of its properties such as thermal and chemical stability, biocompatibility, adsorption capacity, high surface area and ionic substitution ability .…”