Aminocarbonylation of 2-Iodothiophene: High-Yielding Synthesis of Thiophen-2-yl-glyoxylamides

Abstract

2-Iodothiophene has been aminocarbonylated with simple unfunctionalised amines as well as with amino acid esters as N-nucleophiles in the presence of palladium(0) catalysts formed in situ from palladium(II) acetate and triphenylphosphine. While at low carbon monoxide pressure conversions of synthetic interest have been obtained with simple amines only, at higher carbon monoxide pressure various ketocarboxamides, formed via double carbon monoxide insertion, have been isolated with good yields (up to 85%).