Copper-Catalyzed Direct Secondary and Tertiary C[BOND]H Alkylation of Azoles through a Heteroarene–Amine–Aldehyde/Ketone Coupling Reaction

Authors

  • Dipak D. Vachhani,

    1. Department of Chemistry, University of Leuven (KU Leuven), Celestijnenlaan 200F, 3001 Leuven (Belgium)
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  • Dr. Abhishek Sharma,

    1. Department of Chemistry, University of Leuven (KU Leuven), Celestijnenlaan 200F, 3001 Leuven (Belgium)
    2. Present address: Department of Chemistry, University of Illinois at Urbana-Champaign, Urbana, IL 61801 (USA)
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  • Prof. Dr. Erik Van der Eycken

    Corresponding author
    1. Department of Chemistry, University of Leuven (KU Leuven), Celestijnenlaan 200F, 3001 Leuven (Belgium)
    • Department of Chemistry, University of Leuven (KU Leuven), Celestijnenlaan 200F, 3001 Leuven (Belgium)
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  • The authors wish to thank the F.W.O. [Fund for Scientific Research–Flanders (Belgium)] and the Research Fund of the University of Leuven (KU Leuven) for financial support. D.V. is grateful to EMECW15 (Erasmus Mundus External Cooperation Window Lot 15 India) for obtaining a doctoral scholarship. A.S. is thankful to the F.W.O. for obtaining a visiting postdoctoral fellowship.

Abstract

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Coupling the strangers: A copper-catalyzed three-component heteroarene–amine–aldehyde/ketone coupling affords a novel approach to the hitherto difficult direct secondary/tertiary C[BOND]H alkylation of azoles. This simple method allows the facile installation of diversely substituted, branched and nitrogen-containing alkyl or alkaloid side chains on the azole moiety by using readily available starting materials (see scheme).

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