NaIO4-promoted phosphorylation of amines with H-phosphine oxides to construct P(O)-N bonds in water
Huabin Wang1, Qiaoli Li1, Zhiwen Wei1
1College of Pharmacy, Guizhou University of Traditional Chinese Medicine, Guiyang 550025, P. R. China. yingzhou71@sina.com.
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.
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