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Domino Rhodium-Catalyzed Alkyne Arylation/Palladium-Catalyzed N Arylation: A Mechanistic Investigation

Authors

  • Jane Panteleev,

    1. Davenport Research Laboratories, Department of Chemistry, University of Toronto, 80 St George St. Toronto, Ontario, M5S 3H6 (Canada)
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  • Lei Zhang,

    1. Davenport Research Laboratories, Department of Chemistry, University of Toronto, 80 St George St. Toronto, Ontario, M5S 3H6 (Canada)
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  • Prof. Dr. Mark Lautens

    Corresponding author
    1. Davenport Research Laboratories, Department of Chemistry, University of Toronto, 80 St George St. Toronto, Ontario, M5S 3H6 (Canada)
    • Davenport Research Laboratories, Department of Chemistry, University of Toronto, 80 St George St. Toronto, Ontario, M5S 3H6 (Canada)
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  • The authors wish to thank the Natural Sciences and Engineering Research Council (NSERC), Merck for an Industrial Chair, and the University of Toronto for financial support. J.P. thanks NSERC for a CGSD scholarship.

Abstract

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It takes two to tango: A domino multicatalytic synthesis of dihydroquinolines is realized, wherein the products of a rhodium-catalyzed arylation of alkynes are cyclized by a palladium-promoted C[BOND]N cross-coupling (see scheme). The combination of catalysts with potentially exchangeable ligands is remarkable as each metal–ligand combination affords specific reactivity and selectivity.

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