Palladium-Based Catalytic System for the Direct C3-Arylation of Furan-2-carboxamides and Thiophene-2-carboxamides

Authors

  • Karima Si Larbi,

    1. Laboratoire d'hydrométallurgie et chimie inorganique moléculaire Faculté de Chimie, U.S.T.H.B. Bab-Ezzouar (Alger)
    2. Institut Sciences Chimiques de Rennes, UMR 6226, CNRS-Université de Rennes 1, “Catalyse et Organometalliques”, Campus de Beaulieu, 35042 Rennes (France), Fax: (+33) 0223236939
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  • Dr. Hai Yan Fu,

    1. Key Laboratory of Green Chemistry and Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu, 610064 (China)
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  • Nouria Laidaoui,

    1. Laboratoire de Chimie Fine, Département de Chimie, Faculté des Sciences, Université d'Oran Es-Sénia, BP. 1524, EL M'naouer Oran 31100 (Alger)
    2. Institut Sciences Chimiques de Rennes, UMR 6226, CNRS-Université de Rennes 1, “Catalyse et Organometalliques”, Campus de Beaulieu, 35042 Rennes (France), Fax: (+33) 0223236939
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  • Kassem Beydoun,

    1. Institut Sciences Chimiques de Rennes, UMR 6226, CNRS-Université de Rennes 1, “Catalyse et Organometalliques”, Campus de Beaulieu, 35042 Rennes (France), Fax: (+33) 0223236939
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  • Abdellah Miloudi,

    1. Laboratoire de Chimie Fine, Département de Chimie, Faculté des Sciences, Université d'Oran Es-Sénia, BP. 1524, EL M'naouer Oran 31100 (Alger)
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  • Douniazad El Abed,

    1. Laboratoire de Chimie Fine, Département de Chimie, Faculté des Sciences, Université d'Oran Es-Sénia, BP. 1524, EL M'naouer Oran 31100 (Alger)
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  • Safia Djabbar,

    1. Laboratoire d'hydrométallurgie et chimie inorganique moléculaire Faculté de Chimie, U.S.T.H.B. Bab-Ezzouar (Alger)
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  • Dr. Henri Doucet

    Corresponding author
    1. Institut Sciences Chimiques de Rennes, UMR 6226, CNRS-Université de Rennes 1, “Catalyse et Organometalliques”, Campus de Beaulieu, 35042 Rennes (France), Fax: (+33) 0223236939
    • Institut Sciences Chimiques de Rennes, UMR 6226, CNRS-Université de Rennes 1, “Catalyse et Organometalliques”, Campus de Beaulieu, 35042 Rennes (France), Fax: (+33) 0223236939
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Abstract

The palladium-catalyzed direct arylation of furans or thiophenes that contained secondary carboxamides at the C2 position proceeded regioselectively at either the C3 or C5 positions, depending on the reaction conditions. The nature of the base was crucial for controlling the regioselectivity of the reaction. We had previously observed that, in the presence of potassium acetate, direct arylation at the C5 position was favored. Herein, we report that the use of cesium carbonate as the base and xylene as the solvent selectively afforded the C3-arylated furans or thiophenes. The reactivity of furan-2-carboxamides and thiophene-2-carboxamides were similar. The reaction tolerated a range of functional groups on the aryl bromide and also heteroaryl bromide substrates.

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