Phosphine-catalyzed regioselective heteroaromatization between activated alkynes and isocyanides leading to pyrroles

The organophosphine catalyzed reaction of activated alkynes with isocyanides produces the corresponding heteroaromatization products, pyrroles, regioselectively in good yields. The reaction proceeds most probably through the 1,4-addition of the nucleophilic phosphine catalyst to the alkynes, followed by a 3+2] cycloaddition between the resulting alkenyl phosphine intermediates and a carbanion derived from the isocyanides.