Rongalite‐Promoted on Water Synthesis of Functionalised Tellurides and Ditellurides

Abstract

AbstractThe on water reaction of sodium telluride with electrophiles has been explored. Na2Te, generated in situ through the rongalite (sodium hydroxymethanesulfinate)‐promoted reduction of elemental tellurium, reacts with a wide variety of electrophiles, including strained heterocycles, haloalkanes, Michael acceptors, and aryl diazonium salts, providing simple and rapid access to a broad range of novel functionalised symmetrical tellurides. The methodology well tolerated the presence of versatile functional groups such as alchohols, amines, esters, nitriles, and sulfones and allowed the incorporation of tellurium atoms into biologically relevant natural‐derived products. Furthermore, in the case of the nucleophilic ring opening of epoxides and aziridines, a judicious tuning of the reaction conditions enabled the synthesis of unreported β‐hydroxy‐ and β‐amino‐ditellurides, which were further employed as precursors of new functionalised unsymmetrical dialkyl tellurides. The thiol−peroxidase catalytic activity of hydroxy‐ditellurides has also been investigated in order to compare their antioxidant properties with those of homologous tellurides.magnified image