NaIO4-promoted phosphorylation of amines with H-phosphine oxides to construct P(O)–N bonds in water

Abstract

A facile and green protocol for P(O)–N bond formation was discovered through NaIO₄-initiated phosphorylation of stable and readily available amines with secondary phosphine oxides in water. This protocol shows good functional group tolerance and broad substrate scope without metal or base additives, providing an alternative method for constructing P(O)–N bonds. Mechanistic studies suggested that a phosphoryl radical-involving process from secondary phosphine oxides facilitated the phosphorylation of amines in water.