Palladium-catalyzed three-component 1,4-aminoarylation of [60]fullerene with aryl iodides and N-methoxysulfonamides, and further transformations

Abstract

The palladium-catalyzed three-component 1,4-aminoarylation of [60]fullerene with various aryl iodides and N-methoxysulfonamides afforded a series of 1,4-(aryl)(N-methoxysulfonamide)[60]fullerene derivatives under mild reaction conditions. A plausible reaction mechanism for the formation of 1,4-difunctionalized [60]fullerenes was proposed on the basis of experimental results. In addition, further transformations of the formed 1,4-(aryl)(N-methoxysulfonamide)[60]fullerenes in the presence of ferric chloride could replace their N-methoxysulfonamide group by an aryl, heteroaryl, malonate ester or allyl group.