Atom transfer carbonylation using ionic liquids as reaction media

Photo-induced ATC reactions of RI, CO, and amines to produce amides, were examined using ionic liquids, such as bmim]PF₆ and bmim]NTf₂, as reaction media in the presence of a catalytic amount of a Pd–carbene complex. When the primary alkyl iodide was used, the yield of the amide was lowered due to competing S_N2 reactions between RI and amines, whereas the reaction of the tertiary alkyl iodides was dependent on the structure of the substrates. ATC reactions of a wide variety of secondary RI proceeded smoothly when ionic liquids were used as reaction media. The Pd-catalyst and ionic liquid could also be recycled.