Palladium-catalysed aminocarbonylation of iodoarenes and iodoalkenes with aminophosphonate as N-nucleophile

The high-yielding synthesis of novel N-acyl phosphonates with unprecedented structure was carried out by a homogeneous carbonylation reaction under mild reaction conditions. The palladium-catalysed aminocarbonylation of iodoalkenes (1-iodo-cyclohexene, 1-iodo-4-tert-butyl-cyclohexene, 1-iodo-2-methyl-cyclohexene and α-iodostyrene) with diethyl α-aminobenzyl-phosphonate as N-nucleophile resulted in the exclusive formation of carboxamides. The same reaction with iodoaromatics (iodobenzene, 2-iodothiophene) provided the corresponding carboxamide in high yields and some 2-keto-carboxamides as side products due to single and double carbon monoxide insertion, respectively.