Synthesis of New Arylhydroxymethylphosphinic Acids and Derivatives

H.-J. Cristau; A. Hervé; F. Loiseau; D. Virieux

doi:10.1055/s-2003-41045

PAPER

Synthesis of New Arylhydroxymethylphosphinic Acids and Derivatives

H.-J. Cristau*, A. Hervé, F. Loiseau, D. Virieux*
Laboratoire de Chimie Organique, UMR 5076, Ecole Nationale Supérieure de Chimie de Montpellier, 8, Rue de l’Ecole Normale, 34296 Montpellier Cedex 5, France
Fax: +33(4)67144319; e-Mail: cristau@cit.enscm.fr; e-Mail: virieux@cit.enscm.fr ;

Abstract

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Abstract

The synthesis of a new series of arylhydroxymethylphosphinic acid derivatives is described. The protected compounds were prepared by a palladium(0) catalysed arylation of ethyl benzyloxymethylphosphinate with aryl halides. Subsequent hydrogenolysis of the benzyl protecting group followed by acidic hydrolysis of the ester function readily afforded the target compounds. Selective removal of the ester group was achieved by basic hydrolysis whereas acidic hydrolysis directly gave the totally deprotected compounds.

Key words

phosphorus - phosphinates - palladium - arylations - protecting groups

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