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Tosylhydrazide-Promoted Palladium-Catalyzed Reaction of β-Aminoketones with o-Dihaloarenes: Combining Organocatalysis and Transition-Metal Catalysis

Authors

  • Prof. José Barluenga,

    Corresponding author
    1. Instituto Universitario de Química Organometálica “Enrique Moles”, Universidad de Oviedo c/Julián Clavería 8, 33006 Oviedo (Spain), Fax: (+34) 98-510-3446
    • Instituto Universitario de Química Organometálica “Enrique Moles”, Universidad de Oviedo c/Julián Clavería 8, 33006 Oviedo (Spain), Fax: (+34) 98-510-3446
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  • Noelia Quiñones,

    1. Instituto Universitario de Química Organometálica “Enrique Moles”, Universidad de Oviedo c/Julián Clavería 8, 33006 Oviedo (Spain), Fax: (+34) 98-510-3446
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  • Dr. María-Paz Cabal,

    1. Instituto Universitario de Química Organometálica “Enrique Moles”, Universidad de Oviedo c/Julián Clavería 8, 33006 Oviedo (Spain), Fax: (+34) 98-510-3446
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  • Prof. Fernando Aznar,

    1. Instituto Universitario de Química Organometálica “Enrique Moles”, Universidad de Oviedo c/Julián Clavería 8, 33006 Oviedo (Spain), Fax: (+34) 98-510-3446
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  • Dr. Carlos Valdés

    Corresponding author
    1. Instituto Universitario de Química Organometálica “Enrique Moles”, Universidad de Oviedo c/Julián Clavería 8, 33006 Oviedo (Spain), Fax: (+34) 98-510-3446
    • Instituto Universitario de Química Organometálica “Enrique Moles”, Universidad de Oviedo c/Julián Clavería 8, 33006 Oviedo (Spain), Fax: (+34) 98-510-3446
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  • This work was financially supported by the DGI of Spain (CTQ2007-61048/BQU) and the Consejería de Educación y Ciencia of Principado de Asturias (IB08-088). A FICYT predoctoral fellowship to N.Q. is gratefully acknowledged.

Abstract

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Working in tandem: Mannich adducts obtained by organocatalyzed processes are readily transformed into phenanthridine and quinoline derivatives by a Pd-catalyzed cascade reaction involving tosylhydrazide (TsNHNH2)-promoted cross-coupling followed by intramolecular amination (see scheme; MW=microwave). The enantioselectivity achieved in the organocatalytic reaction is maintained throughout the process.

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