Palladium-1,10-phenanthroline complex encaged in Y zeolite: An efficient and highly recyclable heterogeneous catalyst for aminocarbonylation

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

“…A similar phenomenon was observed before by Li and Yuan [11] in double carbonylation with palladium supported on a cross-linked functional polymer.…”

“…As some of the catalysts reported before were shown to be active in apolar solvents, such as toluene [8,9,13,19,22], whereas others gave good results only in polar media [11,24], the catalysts were tested in aminocarbonylation using DMF, acetonitrile and toluene as solvent. analysis of the reaction mixtures) was observed in the first runs of aminocarbonylations carried out in DMF.…”

“…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].…”

“…In all of these double carbonylation reactions, a competing monocarbonylation, leading to amides, was observed. Interestingly, double carbonylation as a side reaction of monocarbonylation under heterogeneous conditions was reported only in one case [11], in spite of the fact that homogeneous catalytic aminocarbonylation may lead to α-ketoamides in considerable amounts even at atmospheric pressure [25].…”

“…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].…”