Solvent-free aminocarbonylation of iodobenzene in the presence of SILP-palladium catalysts

Abstract

The recyclable palladium catalysts were used for selective mono- or double carbonylation under solvent-free conditions and in DMF, respectively.

Application of γ‐Valerolactone as an Alternative Biomass‐Based Medium for Aminocarbonylation Reactions

“…It can be assumed that the higher CO concentration increases the number of coordinated carbonyl ligands on the Pd center, resulting in a lower concentration of coordinatively unsaturated catalytically active species. Similar observations were reported for the SILP‐Pd assisted aminocarbonylation of iodobenzene and synthesis of ferrocene amides . Selectivities for the formation of the corresponding ketocarboxamides were also increased; however, its decrease was not detected at higher pressures.…”

“…Similar observations were reported forthe SILP-Pd assisted aminocarbonylation of iodobenzene and synthesiso ff errocenea mides. [47,48] Selectivities for the formation of the corresponding ketocarboxamides were also increased; however,i ts decrease was not detected at higher pressures.…”

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

“…It is noteworthy that p-substituted amines gave a slightly decreased yield compared with that of o-and m-substituted amines. The substituted amines with electron-withdrawing halogen groups were also tolerated, and gave 66% to 91% yields to the corresponding amides in the order I > Br > Cl (entries [18][19][20][21]. When the amines that have a substituent attached to the amino group were used, the desired products were obtained in moderate yields (entries 22).…”

“…Various heterogeneous palladium catalysts have been reported for the synthesis of amides by aminocarbonylation of aryl halide with CO gas using a support such as silica, carbon, ZIF-8, MCM-41, ionic liquid phases and organic polymers. [12][13][14][15][16][17][18][19] However, these carbonylation reactions over supported palladium catalysts proceeded at high CO pressure and high reaction temperature. Dang group have reported the atmospheric pressure aminocarbonylation of aryl iodides using palladium nanoparticles supported on MOF-5 at 120 C.…”

Mono- and double carbonylation of aryl iodides with amine nucleophiles in the presence of recyclable palladium catalysts immobilised on a supported dicationic ionic liquid phase

“…24 In case of supported catalysts, there are only two reports demonstrating the applicability of the same catalysts in the selective production of either amides or ketoamides: with palladium immobilised on a mesoporous poly-melamineformaldehyde material 25 or on silica functionalised with imidazolium ions. 26 Although both catalysts showed good recyclability, relatively long reaction time (8-12 h) had to be used to achieve total conversion 25 or to ensure effective reuse. 26,27 There are no data for metal leaching in case of the polymer supported catalyst, 25 but in the other case, an average of 2-4% loss of the original load of palladium was still observed in recycling studies.…”