Chelation-Assisted Cross-Coupling of Anilines through In Situ Activation as Diazonium Salts with Boronic Acids under Ligand-, Base-, and Salt-Free Conditions

Authors

  • Roxan Joncour,

    1. Université de Bordeaux, UMR CNRS 5255, ISM, 351, cours de la Libération, 33405 Talence Cedex (France)
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  • Dr. Nicolas Susperregui,

    1. Université de Pau et des Pays de l'Adour, UMR CNRS 5254, IPREM, 2, avenue du Président Pierre Angot, 64053 Pau Cedex 9 (France), Fax: (+33) 559-407-862
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  • Noël Pinaud,

    1. Université de Bordeaux, UMR CNRS 5255, ISM, 351, cours de la Libération, 33405 Talence Cedex (France)
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  • Dr. Karinne Miqueu,

    1. Université de Pau et des Pays de l'Adour, UMR CNRS 5254, IPREM, 2, avenue du Président Pierre Angot, 64053 Pau Cedex 9 (France), Fax: (+33) 559-407-862
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  • Prof. Eric Fouquet,

    1. Université de Bordeaux, UMR CNRS 5255, ISM, 351, cours de la Libération, 33405 Talence Cedex (France)
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  • Dr. Jean-Marc Sotiropoulos,

    Corresponding author
    1. Université de Pau et des Pays de l'Adour, UMR CNRS 5254, IPREM, 2, avenue du Président Pierre Angot, 64053 Pau Cedex 9 (France), Fax: (+33) 559-407-862
    • Université de Pau et des Pays de l'Adour, UMR CNRS 5254, IPREM, 2, avenue du Président Pierre Angot, 64053 Pau Cedex 9 (France), Fax: (+33) 559-407-862
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  • Prof. François-Xavier Felpin

    Corresponding author
    1. Université de Nantes, UFR Sciences et Techniques, UMR CNRS 6230, CEISAM, 2, rue de la Houssinière, BP 92208, 44322 Nantes Cedex 3 (France), Fax: (+33) 251-125-402
    • Université de Nantes, UFR Sciences et Techniques, UMR CNRS 6230, CEISAM, 2, rue de la Houssinière, BP 92208, 44322 Nantes Cedex 3 (France), Fax: (+33) 251-125-402
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Abstract

We describe the coupling of anilines with aryl boronic acids, under ligand-, base-, and salt-free conditions at room temperature. This new reaction proceeds through the formation of an aryl palladium alkoxo complex, which allows the transmetalation step with aryl boronic acids without any external base. Importantly, this sustainable procedure generates only environmentally friendly byproducts such as tBuOH, H2O, N2, and B(OH)3. The reaction mechanism has been deeply investigated through experimental and theoretical studies.

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