Revisited Synthesis of Aryl-H-phosphinates

Jean-Noël Volle; Damien Filippini; Camille Midrier; Michal Sobecki; Marcin Drag; David Virieux; Jean-Luc Pirat

doi:10.1055/s-0030-1260109

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Synthesis 2011(15): 2490-2494
DOI: 10.1055/s-0030-1260109

PAPER

Revisited Synthesis of Aryl-H-phosphinates

Jean-Noël Volle*^a, Damien Filippini^a, Camille Midrier^a, Michal Sobecki^b, Marcin Drag^b, David Virieux^a, Jean-Luc Pirat^a
^a Institut Charles Gerhardt UMR5253, AM2N, ENSCM, 8 Rue de l’Ecole Normale, 34296 Montpellier Cedex 5, France
Fax: +33(4)67144319; e-Mail: jean-noel.volle@enscm.fr;
^b Department of Medicinal Chemistry and Microbiology, Faculty of Chemistry, Wroclaw University of Technology, Wybrzeze Wyspianskiego 27, 50-370 Wroclaw, Poland

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Publikationsverlauf

Received 19 April 2011
Publikationsdatum:
14. Juli 2011 (online)

Abstract
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Abstract

A systematic study of the reaction conditions for the preparation of pure aryl-H-phosphinate esters, originally developed by Sander and optimized by Petneházy, is reported. The influence of the reaction concentration has been investigated for the formation of phosphonite intermediates via direct addition of triethyl phosphite to the appropriate Grignard reagent. Subsequent hydrolysis of the phosphonites under acidic conditions gives various aryl-H-phosphinates in high yields and purities.

Key words

phosphonites - phosphinates - aryl-H-phosphinates - triethyl phosphite - hydrolysis - Grignard reagent

References

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