Palladium-Catalyzed Aminocarbonylation of Iodoalkenes and Iodoarenes

Rita      Skoda-Foldes; Laszlo      Kollar

Abstract

In this minireview, the most important recent results in homogeneous catalytic aminocarbonylations, achieved by the authors during the last 5 years, are surveyed. The widely used palladium catalyst precursors, the in situ formation of palladium(0) catalysts, as well as the reaction mechanism of the palladium-catalysed carbonylations based on the application of carbon monoxide are discussed. The aminocarbonylation of iodoarenes and iodoalkenes as simple model compounds and similar substrates of practical importance, possessing either steroidal, tropane or cyclic terpene skeleton, were carried out. A great variety of primary and secondary amines of different structure, including amino acid derivatives, were used as N-nucleophiles leading to the target unsaturated or aromatic carboxamides.

Keywords: Palladium, carbon monoxide, aminocarbonylation, iodoarene, iodoalkene, iodoalkenes, N-nucleophiles, steroids, alkaloids, terpenes, carbonylations, PdCl2(MeCN)2, Pd(OAc)2, amines, alkenes, phosphines, PPh3, Pd-R, Pd(II), CO, DBU, N-heterocycles, DMF, carboxamides, N-nucleophile, hydrazones, morpholine, piperidine