TEMPO/PhI(OAc)2 promotes the α-aminophosphinoylation of alcohols with amines and H-phosphine oxides in aqueous medium

Abstract

A novel method for synthesizing α-aminoalkyl phosphine oxides in aqueous medium, using Ar₂P(O)–H reagents, alcohols and amines, is described. This method: (i) allows for the smooth aminophosphinoylation of alcohols with amines and H-phosphine oxides under mild conditions; (ii) provides an efficient and alternative approach to access various α-aminoalkylphosphine oxides. Although various amines exhibited remarkable versatility and tolerance for functional groups in this reaction, alcohols and H-phosphine oxides demonstrated limited applicability as reactants. Hence, further investigation using a wider range of substrates is crucial. The postulated mechanism indicated that the three-component reaction followed the imine pathway due to the in situ oxidation of alcohol to aldehyde.