Polymer supported Pd catalyzed carbonylation of aryl bromides for the synthesis of aryl esters and amides

Abstract

A new polymer anchored Pd(ii) Schiff base catalyst has been synthesized for the evaluation of alkoxycarbonylation and aminocarbonylation reactions of various substituted aryl bromides with alcohols and amines.

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

“…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.…”

“…Some previous reports show the excellent activity of immobilised palladium catalysts in toluene [8,9,13,19,22], so the possibility of the use of this solvent was also taken into account. As it was observed before in the case of CAT-1/1 and CAT-2/1 [26], the use of an apolar solvent reduced catalytic efficiency considerably in all of the catalysts investigated ( Figure 6).…”

“…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].…”

“…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].…”

Silver nanoparticles embedded over porous metal organic frameworks for carbon dioxide fixation via carboxylation of terminal alkynes at ambient pressure

“…Recently, we have reported several efficient methodologies for the carbonylation [73][74][75] of aryl halides using carbon monoxide as a C1 source. However, CO is a toxic gas and thus here catalytic activity is observed.…”