Amino- and azidocarbonylation of iodoalkenes

Abstract

Iodoalkenes, available from ketones via their hydrazones, underwent palladium-catalysed azidocarbonylation. Depending on the structure of the acyl azides, consecutive hydrolysis toward corresponding primary amides was observed. ‘Direct’ aminocarbonylation of the same iodoalkenes was also carried out by using ammonium carbamate as ammonia source under mild conditions. The α,β-unsaturated primary amides, formed in a chemoselective reaction, were isolated in good to excellent yields.