Umpolung strategy for the electrochemical synthesis of novel anthraquinone-based sulfonamide derivatives: a facile and sustainable strategy

Abstract

A facile and sustainable galvanostatic strategy was developed for the synthesis of novel sulfonamide derivatives containing anthraquinone moieties. These syntheses were successfully carried out in a divided cell (divided by glass frit) using a graphite anode and a stainless steel cathode in water/acetonitrile solutions at room temperature. The Umpolung strategy employed in these syntheses is straightforward. It is based on the oxidative conversion of 1,4-diaminoanthraquinone from a nucleophile to an electrophile, followed by its reaction with arylsulfinic acid derivatives. The synthesis strategy, as well as the mechanism governing it, has been determined based on the differences in data obtained from electrochemical studies on the oxidation of 1,4-diaminoanthraquinone in the absence and presence of arylsulfinic acid derivatives. This process exhibits high atom economy, does not require a catalyst, is carried out in one pot, is easily scalable, and can be used for a wide range of arylsulfinic acid derivatives.