Facile synthesis of primary amides and ketoamides via a palladium-catalysed carbonylation–deprotection reaction sequence

Abstract

Various primary amides and ketoamides have been obtained in good yields in a two-step reaction sequence. The first step involves the synthesis of aryl/alkenyl N- tert-butyl amides and aryl N- tert-butyl ketoamides from the corresponding iodides via palladium-catalysed carbonylation in the presence of t-BuNH 2 as the nucleophile. Carbonylation was followed by selective cleavage of the t-Bu group using TBDMSOTf as the reagent.