An efficient one-step synthetic strategy was used to prepare a set of dicarboxamides through palladium-catalysed aminocarbonylation of iodoalkenyl and iodoaryl compounds, with use of various alkyl-and aryldiamines as N-nucleophiles. The isolated yields of the dicarboxamides depended significantly on the iodo substrate and diamine structures, as well as on the reaction conditions, the best one (ca. 70 %) being achieved with 1-iodocyclohexene as substrate and 1,4-diaminobutane as nucleophile, at 100°C and 30 bar of CO.

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Novel androstene-based dimers linked through A-and D-ring with 3,3 0 -and 17,17 0 -dicarboxamide spacers, were synthesized via palladium-catalyzed aminocarbonylation. Androstane derivatives possessing either 3-iodo-3,5-diene or 17-iodo-16-ene functionality were used as substrates in the presence of palladium-phosphine in situ catalysts and aliphatic and aromatic diamines as N-nucleophiles. Since androst-4-ene-3,17-dione was used as starting material, a multistep synthesis including protection/deprotection of one of the keto functionalities (3-one or 17-one) as ethylene ketals, transformation of the other keto group to iodoalkene functionality via its hydrazone, and palladium-catalyzed aminocarbonylation of the iodoalkene functionality was used. In this way, new dimeric compounds possessing a keto functionality were obtained in moderate-to-good isolated yields, via highly chemoselective reactions, under relatively mild conditions.