Immobilized Palladium Metal-Containing Ionic Liquid-Catalyzed Alkoxycarbonylation, Phenoxycarbonylation, and Aminocarbonylation Reactions

Abstract

Immobilized palladium metal-containing ionic liquid (ImmPd-IL), a structurally well-defined transition metal complex, is explored as an immobilized, phosphine-free catalyst for carbonylation reactions, including alkoxycarbonylation, phenoxycarbonylation, and aminocarbonylation reactions. The effect of various reaction parameters, such as solvent, base, time, temperature, and CO pressure on carbonylation reactions using ImmPd-IL catalyst was investigated. The optimized protocol was applied to a wide variety of substituted aryl iodides and various alcohol/phenols and amines having different steric and electronic properties and afforded the corresponding products in good to excellent yield. The developed catalytic system circumvents the use of phosphine ligands, with an additional advantage of palladium catalyst recovery and reuse for up to four consecutive cycles. The recycled catalyst was characterized using XPS analysis.

Mono- and double carbonylation of iodobenzene in the presence of reusable supported palladium catalysts

“…A great variety of supported palladium catalysts were tested, such as Pd/C [6], a polymer- [7] or silica-supported palladium-N-heterocyclic carbene- [8], palladium-Schiff base- [9] or palladiumphosphine complex, [10], a palladium-phenantroline derivative encaged in Y-zeolite [11], and Pd nanoparticles immobilised on a zeolitic imidazole framework [12] or on carbon nanotubes [13]. In some cases, carbonylation could be carried out at atmospheric pressure, e.g., in the presence of palladium complexes with bidentate ligands anchored on MCM-41 [14] or on silica [15][16][17], as well as using palladium nanoparticles supported on a metalorganic framework [18] or on a siliceous mesocellular foam [19].…”

“…In some cases, carbonylation could be carried out at atmospheric pressure, e.g., in the presence of palladium complexes with bidentate ligands anchored on MCM-41 [14] or on silica [15][16][17], as well as using palladium nanoparticles supported on a metalorganic framework [18] or on a siliceous mesocellular foam [19]. Whereas an efficient recycling can be achieved in most cases at elevated pressure [7][8][9][11][12][13][14][15][16][17][18][19], under atmospheric conditions a substantial drop of activity was often observed upon the reuse of the catalyst [18,19].…”

Ionic liquid attached to colloidal silica nanoparticles: as high performance catalyst for the preparation of dihydrofurans under microwave irradiation

“…Ionic liquids can be considered as valuable key precursor compounds for catalysts [23][24][25][26][27][28][29]. The nature of cation-anion interactions in ambient temperature ionic liquids is an issue of increasing interest [30,31].…”

Facile TEMPO Immobilization onto Poly(acrylic acid)-Modified Magnetic Nanoparticles: Preparation and Property

“…Recently, different types of catalyst support materials such as polymer supports [4][5][6][7][8][9][10], ionic liquid supports [10][11][12], inorganic supports [13][14][15][16][17][18], metal organic frame supports [19], and nanocomposite supports [20][21][22] have been invented for immobilizing catalysts on beads, surfaces, and membranes, and so forth [23]. Of these, magnetic iron oxide nanocomposites have been the most widely used support material [2] because they offer enormous surface area with more binding sites; this reduces the disadvantages of heterogeneous catalysis [24].…”