Synthesis of N-picolylcarboxamides in aminocarbonylation

Abstract

Palladium-catalysed aminocarbonylation of iodocamphene and steroidal iodoalkenes was carried out in the presence of 2-, 3- and 4-picolylamine, as well as secondary amines possessing 1-picolyl substituent. In general, primary picolylamines require less than 2 h to achieve practically complete conversion. The secondary amines proved to be less reactive, requiring 6–24 h depending on the substrate structure. The corresponding carboxamides were isolated in moderate to excellent yields. The synthesis of α,β-unsaturated carboxamides is based on the synthesis of iodoalkene substrates from enolizable ketones. • Facile synthesis of unsaturated carboxamides in palladium-catalysed aminocarbonylation. • High-yielding functionalization of camphene and steroidal skeletons. • The use of easily available, reactive iodoalkene substrates.