Synthesis of Ferrocenylacrylamides via Homogeneous Catalytic Aminocarbonylation of 1-Ferrocenyl-1-Iodoethene

A highly reactive 1-ferrocenyl-1-iodoethene was prepared from acetylferrocene via its hydrazone and used as substrate in palladium-catalysed aminocarbonylation. The iodoalkenyl substrate proved to be reactive in the presence of various simple primary and secondary amines, as well as amino acid esters as N -nucleophiles under atmospheric or high pressure carbon monoxide at 50 o C or 100 o C, respectively. The corresponding N -substituted 1-ferrocenylacrylamides were formed in a highly chemoselective reaction enabling moderate to high isolated yields (up to 99%). • Efficient synthesis for widely applicable 1-ferrocenyl-1-iodoethene was developed. • Highly chemoselective palladium-catalysed aminocarbonylation of the above substrate was carried out. • N -Substituted 1-ferrocenylacrylamides were synthesised in moderate to high isolated yields.