Aminocarbonylation of aryl iodides with primary and secondary amines in aqueous medium using polymer supported palladium-N-heterocyclic carbene complex as an efficient and heterogeneous recyclable catalyst

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

“…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].…”

“…Similar systems supported on silica [8,27] or a polymer [7] were applied for monocarbonylation by others. However, there was no indication why those particular sets of conditions (PdCl 2 precursor immobilised in acetonitrile on silica functionalised by imidazolium chloride [8,27] and Pd(OAc) 2 precursor supported in DMF and aq.…”

“…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].…”

Phosphine-free atmospheric carbonylation of aryl iodides with aniline derivatives in the presence of a reusable silica-supported palladium catalyst

“…Although amides can be prepared under mild reaction conditions by the use of homogeneous palladium catalysts, as the synthesis of N-substituted phthalimides [7] were performed in the presence of Pd/C under 5-9 bar CO pressure. A polymer supported palladium-N-heterocyclic carbene complex was shown to be a recyclable catalyst in aminocarbonylations under 6.9 bar CO [8]. A palladium catalyst, immobilised by a bidentate phosphine ligand grafted on Merrifield resin, was reported to convert bromoarenes to amides at 4.8 bar CO [9].…”

Ligand-free Pd(0)/SiO2-catalyzed aminocarbonylation of aryl iodides to amides under atmospheric CO pressure

“…Different substituted amines were also tested. Good yields of 84% to 99% were obtained for the amines with electron-donating groups (entries [12][13][14][15][16]. It is noteworthy that p-substituted amines gave a slightly decreased yield compared with that of o-and m-substituted amines.…”