Issue 8, 2022

Metal-free C(aryl)–P bond cleavage: experimental and computational studies of the Michael addition/aryl migration of triarylphosphines to alkynyl esters

Abstract

The nucleophilic addition and aryl migration of triarylphosphines to alkynyl esters in the presence of water results in the formation of 3-(diarylphosphoryl)-3-aryl propanoic acid derivatives through a metal-free C(aryl)–P bond cleavage process. Experimental and computational investigations of the mechanism indicate that the rapid formation of hydroxy-λ5-phosphane as a key intermediate plays a crucial role in smooth C(aryl)–P bond cleavage.

Graphical abstract: Metal-free C(aryl)–P bond cleavage: experimental and computational studies of the Michael addition/aryl migration of triarylphosphines to alkynyl esters

Supplementary files

Article information

Article type
Research Article
Submitted
09 Jan 2022
Accepted
05 Mar 2022
First published
07 Mar 2022

Org. Chem. Front., 2022,9, 2187-2192

Metal-free C(aryl)–P bond cleavage: experimental and computational studies of the Michael addition/aryl migration of triarylphosphines to alkynyl esters

M. Sako, K. Kanomata, M. S. H. Salem, T. Furukawa, H. Sasai and S. Takizawa, Org. Chem. Front., 2022, 9, 2187 DOI: 10.1039/D2QO00028H

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