Palladium-catalysed selective aminocarbonylation of 1′,4-diiodostyrene

1′,4-Diiodostyrene possessing both iodo-aryl and iodo-alkenyl functionalities was prepared and used as substrate in palladium-catalysed aminocarbonylation. The corresponding dicarboxamides were obtained as major products in high yields by using several amine nucleophiles including amino acid methyl esters. Due to the highly different reactivity of the two iodo-functionalities, the selective aminocarbonylation of the iodo-vinyl moiety was carried out at atmospheric carbon monoxide pressure resulting in the formation of 4-iodo-phenyl-acrylamides. The latter amides were used as substrates in high pressure aminocarbonylation resulting in amide-ketocarboxamide type products. The latter functionality was formed via double carbon monoxide insertion into the iodo-aryl bond.