A Copper-Catalyzed Variant of the Michaelis–Arbuzov Reaction

Authors

  • Jorge Ballester,

    1. CNRS, UMR 5253, Institut Charles Gerhardt Montpellier, ENSCM, 8, rue de l'Ecole Normale, 34296 Montpellier (France), Fax: (+33) 467-144-319
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  • Jérémie Gatignol,

    1. Laboratoire de Chimie Moléculaire et Thio-organique, CNRS, UMR 6507, INC3 M FR3038, ENSICAEN & Université de Caen Basse-Normandie, 6 Boulevard du Maréchal Juin, 14050 Caen (France), Fax: (+33) 231-452-877
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  • Guntram Schmidt,

    1. CNRS, UMR 5253, Institut Charles Gerhardt Montpellier, ENSCM, 8, rue de l'Ecole Normale, 34296 Montpellier (France), Fax: (+33) 467-144-319
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  • Dr. Carole Alayrac,

    1. Laboratoire de Chimie Moléculaire et Thio-organique, CNRS, UMR 6507, INC3 M FR3038, ENSICAEN & Université de Caen Basse-Normandie, 6 Boulevard du Maréchal Juin, 14050 Caen (France), Fax: (+33) 231-452-877
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  • Prof. Annie-Claude Gaumont,

    Corresponding author
    1. Laboratoire de Chimie Moléculaire et Thio-organique, CNRS, UMR 6507, INC3 M FR3038, ENSICAEN & Université de Caen Basse-Normandie, 6 Boulevard du Maréchal Juin, 14050 Caen (France), Fax: (+33) 231-452-877
    • Annie-Claude Gaumont, Laboratoire de Chimie Moléculaire et Thio-organique, CNRS, UMR 6507, INC3 M FR3038, ENSICAEN & Université de Caen Basse-Normandie, 6 Boulevard du Maréchal Juin, 14050 Caen (France), Fax: (+33) 231-452-877===

      Marc Taillefer, CNRS, UMR 5253, Institut Charles Gerhardt Montpellier, ENSCM, 8, rue de l'Ecole Normale, 34296 Montpellier (France), Fax: (+33) 467-144-319===

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  • Dr. Marc Taillefer

    Corresponding author
    1. CNRS, UMR 5253, Institut Charles Gerhardt Montpellier, ENSCM, 8, rue de l'Ecole Normale, 34296 Montpellier (France), Fax: (+33) 467-144-319
    • Annie-Claude Gaumont, Laboratoire de Chimie Moléculaire et Thio-organique, CNRS, UMR 6507, INC3 M FR3038, ENSICAEN & Université de Caen Basse-Normandie, 6 Boulevard du Maréchal Juin, 14050 Caen (France), Fax: (+33) 231-452-877===

      Marc Taillefer, CNRS, UMR 5253, Institut Charles Gerhardt Montpellier, ENSCM, 8, rue de l'Ecole Normale, 34296 Montpellier (France), Fax: (+33) 467-144-319===

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Abstract

As part of our studies on copper-catalyzed arylation of nucleophiles, we report on Michaelis–Arbuzov reactions with a novel catalytic system, featuring a copper(I) salt as precatalyst without any additional ligand. This procedure is an interesting alternative to the use of expensive and toxic transition metals (nickel, palladium) traditionally used as catalysts in Michaelis–Arbuzov reactions. Our approach allows the synthesis from triethylphosphite, diethyl aryl phosphonite, and diaryl ethylphosphinite of various aryl phosphonates, aryl phosphinates, and aryl phosphine oxides, respectively. These families of compounds are essential owing to their respective importance in bioorganic and medical chemistry, their applicability as flame retardants, and their usability in coordination chemistry and catalysis.

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