Issue 78, 2023

Unexpected rapid P-stereomutation of phosphine oxides catalysed by chlorophosphonium salts

Abstract

P-Stereomutation of phosphine oxides is extremely slow. We show that it is catalysed by chlorophosphonium salts (CPS) which can directly be formed in the system in situ. The racemization of phosphine oxides at ambient conditions catalysed by 1 mol% of CPS takes 1–2 hours and can be arrested by additon of a primary alcohol. The process probably proceeds via the development of oxodiphosphonium P–O–P species.

Graphical abstract: Unexpected rapid P-stereomutation of phosphine oxides catalysed by chlorophosphonium salts

Supplementary files

Article information

Article type
Communication
Submitted
01 Aug 2023
Accepted
07 Sep 2023
First published
13 Sep 2023
This article is Open Access
Creative Commons BY-NC license

Chem. Commun., 2023,59, 11696-11699

Unexpected rapid P-stereomutation of phosphine oxides catalysed by chlorophosphonium salts

S. Al-Sulaimi, K. Rajendran, K. Nikitin and D. G. Gilheany, Chem. Commun., 2023, 59, 11696 DOI: 10.1039/D3CC03719C

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