Cutting edge of diphenyl phosphorazidate (DPPA) as a synthetic reagent–A fifty-year odyssey

• Takayuki Shioiri^a
• Kotaro Ishihara^a
• Masato Matsugi^a

• ^aFaculty of Agriculture, Meijo University, Shiogamaguchi, Tempaku, Nagoya 468-8502, Japan

Recent advances of diphenyl phosphorazidate (DPPA) as a versatile synthetic reagent was described. It works as an azide anion equivalent, 1,3-dipole, electrophile, and nitrene. Thus it can be conveniently used for amide synthesis, ester synthesis, modified Curtius reaction, phosphorylation, C-acylation, azide synthesis, Pummerer rearrangement, cycloadditions, diazotization, triazoline formation, Staudinger reaction, amidine and guanidine synthesis, C–H phosphorazidation, nitrene insertion, decarbonylation, etc.

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