Synthesis of nitroarenes and azoxyarenes through the selenium-mediated on water oxidation of aryl amines

Abstract

Selenium-promoted oxidations enable a broad range of valuable oxidative functional group interconversions. Anilines are oxidized with hydrogen peroxide in water in the presence of selenium catalysts. The selenium catalyst determines the nature of the oxidation product; whereas nitroarenes are obtained employing diphenyl diselenide or benzeneseleninic acid, azoxyarenes are formed using selenium dioxide or sodium seleninate. The reaction mechanism relies on the reactivity of Se(IV) active oxidants, while Se(VI) species have been demonstrated not to be involved in.