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Synthesis 2011(15): 2490-2494  
DOI: 10.1055/s-0030-1260109
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Revisited Synthesis of Aryl-H-phosphinates

Jean-Noël Volle*a, Damien Filippinia, Camille Midriera, Michal Sobeckib, Marcin Dragb, David Virieuxa, Jean-Luc Pirata
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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Publication History

Received 19 April 2011
Publication Date:
14 July 2011 (online)

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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

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