High-yielding synthesis of 1-carboxamido-3,4-dihydronaphthalenes via palladium-catalyzed aminocarbonylation

1-Iodo-3,4-dihydronaphthalene, an iodoalkene substrate obtained from α-tetralon, has been carbonylated in the presence of palladium-phosphine precatalysts. Systematic investigations have revealed that the 1-carboxamido-3,4-dihydronaphthalenes and 1-methoxycarbonyl-3,4-dihydronaphthalene have been formed in exceptionally high isolated yields (up to 96%) in chemospecific reaction. The influence of the amine nucleophile and that of the reaction conditions (carbon monoxide pressure, reaction temperature) on the reactivity of the substrate have been investigated.