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

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 -BuNH2 as the nucleophile. Carbonylation was followed by selective cleavage of the t-Bu group using TBDMSOTf as the reagent. (c) 2007 Elsevier Ltd. All rights reserved.