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(N)2 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. (c) 2006 Elsevier B.V. All rights reserved.