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Versatile Pd-Catalyzed C[BOND]H Oxidative Cyclization of Homoallylhydrazones to Pyrazolines and Tetrahydropyridazines

Authors

  • Cleve Dionel Mboyi,

    1. CNRS (Le Centre National de la Recherche Scientifique), LCC (Laboratoire de Chimie de Coordination), 205, Route d Narbonne, 31077 Toulouse (France), Fax: (+33) 5-61-55-30-03
    2. Université de Toulouse, UPS, INP, LCC (Laboratoire de Chimie de Coordination), 205, route de Narbonne, 31077 Toulouse (France)
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  • Dr. Ibrahim Abdellah,

    1. CNRS (Le Centre National de la Recherche Scientifique), LCC (Laboratoire de Chimie de Coordination), 205, Route d Narbonne, 31077 Toulouse (France), Fax: (+33) 5-61-55-30-03
    2. Université de Toulouse, UPS, INP, LCC (Laboratoire de Chimie de Coordination), 205, route de Narbonne, 31077 Toulouse (France)
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  • Carine Duhayon,

    1. CNRS (Le Centre National de la Recherche Scientifique), LCC (Laboratoire de Chimie de Coordination), 205, Route d Narbonne, 31077 Toulouse (France), Fax: (+33) 5-61-55-30-03
    2. Université de Toulouse, UPS, INP, LCC (Laboratoire de Chimie de Coordination), 205, route de Narbonne, 31077 Toulouse (France)
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  • Dr. Yves Canac,

    Corresponding author
    1. CNRS (Le Centre National de la Recherche Scientifique), LCC (Laboratoire de Chimie de Coordination), 205, Route d Narbonne, 31077 Toulouse (France), Fax: (+33) 5-61-55-30-03
    2. Université de Toulouse, UPS, INP, LCC (Laboratoire de Chimie de Coordination), 205, route de Narbonne, 31077 Toulouse (France)
    • CNRS (Le Centre National de la Recherche Scientifique), LCC (Laboratoire de Chimie de Coordination), 205, Route d Narbonne, 31077 Toulouse (France), Fax: (+33) 5-61-55-30-03
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  • Prof. Remi Chauvin

    Corresponding author
    1. CNRS (Le Centre National de la Recherche Scientifique), LCC (Laboratoire de Chimie de Coordination), 205, Route d Narbonne, 31077 Toulouse (France), Fax: (+33) 5-61-55-30-03
    2. Université de Toulouse, UPS, INP, LCC (Laboratoire de Chimie de Coordination), 205, route de Narbonne, 31077 Toulouse (France)
    • CNRS (Le Centre National de la Recherche Scientifique), LCC (Laboratoire de Chimie de Coordination), 205, Route d Narbonne, 31077 Toulouse (France), Fax: (+33) 5-61-55-30-03
    Search for more papers by this author

Abstract

Pd-catalyzed 5-exo-trig or 6-endo-trig C[BOND]H oxidative cyclization of C-homoallyl-N-sulfonylhydrazones to 5-vinylpyrazolines or 6-methylidene-1,4,5,6-tetrahydropyridazines, respectively, is shown to be controlled in a highly selective manner by the ionic character of the PdII catalytic center. This character is ultimately defined by the nature of the X ligand in the PdX2 salt serving as an in situ precursor of the active catalytic species involving BIPHIMIP {2-(diphenylphosphino)-1-[2-(diphenylphosphino)phenyl]-1H-imidazole} as an optimal spectator diphosphine ligand for both processes. Whereas acetates (X=OAc) favor the 6-endo process, noncoordinating anions such as tosylates and triflates (X=OTs, OTf) favor the 5-exo process.

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