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Decarboxylative Heterocoupling Coupling of Substituted Benzoic Acids for Biaryl Synthesis

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Abstract

The heterocoupling between 2-nitrobenzoic and 2,6-dimethoxybenzoic acids was studied. It was demonstrated that the [PdCl2/Cu(OH)2:0.2/0.75 equiv.] catalytic system can catalyze this reaction with significant yield. Further optimizations (i.e.: sources and loadings of copper and palladium salts, base) allowed to isolate the biaryl in 70 % yield. A catalytic cycle that accounts for the observed results is proposed. While the bi-metal catalyst has shown high yields with some substrates, it is only able to catalyze the decarboxylative coupling in high yield for some of the substrates studied.

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Acknowledgments

The authors gratefully acknowledge the National Agency of Research (CHEMLIVAL N° ANR-12-CDII-0001_01) for funding. N.R. thanks the Ministry of Research and Education for Grant.

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Authors and Affiliations

  1. 1–IRCELYON, Institut de Recherches sur la Catalyse et l’Environnement de Lyon, UMR 5226, CNRS-Université Lyon1, 2 Avenue Albert Einstein, 69626, Villeurbanne Cedex, France

    Nelly Rameau, Stéphane Cadot, Anthony Paquet, Catherine Pinel & Laurent Djakovitch

Authors
  1. Nelly Rameau
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  2. Stéphane Cadot
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  3. Anthony Paquet
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  4. Catherine Pinel
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  5. Laurent Djakovitch
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Corresponding authors

Correspondence to Catherine Pinel or Laurent Djakovitch.

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Rameau, N., Cadot, S., Paquet, A. et al. Decarboxylative Heterocoupling Coupling of Substituted Benzoic Acids for Biaryl Synthesis. Top Catal 57, 1430–1437 (2014). https://doi.org/10.1007/s11244-014-0308-2

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  • DOI: https://doi.org/10.1007/s11244-014-0308-2

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