Issue 24, 2023

Azaphosphinines and their derivatives

Abstract

Six-membered heterocycles containing one phosphorus and one nitrogen atom, known as azaphosphinines, have existed in the shadows of their single heteroatom-containing analogues for almost 150 years. Despite this, recent chemistry has seen a rapid increase in publications concerning this uncommon scaffold. Azaphosphinines exist in one of six isomers—there are three possible orientations of the pnictogen atoms and in each of these, the phosphorus is in one of two valences (PIIIvs. PV). This review aims to outline and inform on the synthesis and applications of all six isomers. PV–oxo azaphosphinines are of particular interest to this review as many of the discussed heterocycles either form as the pentavalent species directly or oxidize to this over time. In very recent years the published applications of azaphosphinines have blossomed into subjects spanning several fields of chemistry such as asymmetric catalysis, supramolecular association, cellular imaging, and medicinal chemistry.

Graphical abstract: Azaphosphinines and their derivatives

Article information

Article type
Review Article
Submitted
04 Leo 2023
First published
24 Pun 2023

Chem. Soc. Rev., 2023,52, 8599-8634

Azaphosphinines and their derivatives

J. N. McNeill, J. P. Bard, D. W. Johnson and M. M. Haley, Chem. Soc. Rev., 2023, 52, 8599 DOI: 10.1039/D3CS00737E

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