Issue 12, 2022

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

Abstract

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.

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

Article information

Article type
Review Article
Submitted
12 Mär 2022
Accepted
04 Mai 2022
First published
05 Mai 2022

Org. Chem. Front., 2022,9, 3360-3391

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

T. Shioiri, K. Ishihara and M. Matsugi, Org. Chem. Front., 2022, 9, 3360 DOI: 10.1039/D2QO00403H

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