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, Email: cristaucit.enscm.fr, virieuxcit.enscm.fr

H.-J. Cristau, A. Hervé, F. Loiseau, D. Virieux, Synthesis, 2003, 2216-2220.

DOI: 10.1055/s-2003-41045

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Abstract

Arylhydroxymethylphosphinic acid derivatives were prepared by a palladium(0) catalysed arylation of ethyl benzyl­oxymethylphosphinate with aryl halides followed by subsequent hydrogenolysis of the benzyl protecting group and hydrolysis of the ester function.

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Details

Several aryl- or heteroarylhydroxymethylphosphinic acid derivatives were prepared by palladium(0) catalysed arylation of ethyl benzyloxymethylphosphinate (3), with aromatic or heteroaromatic bromides or iodides. Finally, total or selective deprotections have been performed to confirm the compatibility and the complementarity of the protecting groups on the phosphorus atom and on the hydroxymethyl group. The synthetic sequence affords a reliable and general access to this class of phosphinic acids.

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Key Words

phosphorus, phosphinates, palladium, arylations, protecting groups, benzyl ethers

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ID: J66-Y2003-2020