Mild hypervalent iodine mediated oxidative nitration of N-aryl sulfonamides

Abstract

An oxidative and acid-free method for the nitration of N-aryl sulfonamides has been developed using a combination of sodium nitrite as cheap and easy to handle NO₂-source and the hypervalent iodine reagent PIFA as stoichiometric oxidant. Under very mild reaction conditions, the desired mononitrated aryl sulfonamides were isolated in up to 87% yield. This is the first example of an iodane-mediated oxidative nitration.