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

• Published in: Organic & biomolecular chemistry Vol. 22; no. 19; pp. 386 - 3865
• Main Authors: Huang, Qiang, Jin, Xin, Wu, Lvjia, Li, Jiangdong, Xing, Qianlu, Wang, Xianheng, Zhao, Changkuo
• Format: Journal Article
• Published: 15.05.2024
• ISSN: 1477-0520; 1477-0539
• DOI: 10.1039/d4ob00302k

A novel method for synthesizing α-aminoalkyl phosphine oxides in aqueous medium, using Ar 2 P(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. The aminophosphinoylation of alcohols with amines and H-phosphine oxides provides an efficient and mild approach to access various α-aminoalkylphosphine oxides in good yields with good tolerance of functional groups using H 2 O as a clean solvent.