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 SN2 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.

Photo-induced atom transfer carbonylation of a wide variety of RI proceeded well using ionic liquids in the presence of Pd–carbene complex, whereas primary RI were not suitable for the present system because of competing SN2 reactions.Figure optionsDownload as PowerPoint slide