Functionalization of intact trimetaphosphate: A triphosphorylating reagent for C, N, and O nucleophiles

Trimetaphosphate (TriMP, [P3O9]^3-) reacts with PyAOP ((7-azabenzotriazol-1-yloxy)tripyrrolidinophosphonium hexafluorophosphate) to yield a new activated TriMP. This electrophilic species bears a phosphonium moiety which acts as a potent leaving group, forming a neutral phosphoramide upon treatment with suitable nucleophiles. Treatment of the activated TriMP with nucleophiles generates new compounds in which an intact metaphosphate ring is appended with a new organic or inorganic functional group. A variety of C, N, and O nucleophiles result in phosphonate, phosphoramidate, phosphate, and organophosphate products. Subsequent hydrolysis of these intact metaphosphate species ring opens to linear triphosphate derivatives with potential applications in biochemistry, coordination chemistry, and materials science.