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Asymmetric Intramolecular Hydroamination of Alkenes in Mild and Wet Conditions—Structure and Reactivity of Cationic Binuclear Gold(I) Catalysts

Authors

  • Marc-Antoine Abadie,

    1. Unité de Catalyse et de Chimie du Solide, UCCS, CNRS, UMR 8181, Université Lille Nord de France, 59655 Villeneuve d'Ascq (France), Fax: (+33) 320436585
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  • Dr. Xavier Trivelli,

    1. Unitéde Glycobiologie Structurale et Fonctionnelle, UGSF, CNRS, UMR 8576, Université Lille Nord de France, Université Lille Nord de France, 59655 Villeneuve d'Ascq Cedex (France)
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  • Florian Medina,

    1. Unité de Catalyse et de Chimie du Solide, UCCS, CNRS, UMR 8181, Université Lille Nord de France, 59655 Villeneuve d'Ascq (France), Fax: (+33) 320436585
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  • Dr. Frédéric Capet,

    1. Unité de Catalyse et de Chimie du Solide, UCCS, CNRS, UMR 8181, Université Lille Nord de France, 59655 Villeneuve d'Ascq (France), Fax: (+33) 320436585
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  • Dr. Pascal Roussel,

    1. Unité de Catalyse et de Chimie du Solide, UCCS, CNRS, UMR 8181, Université Lille Nord de France, 59655 Villeneuve d'Ascq (France), Fax: (+33) 320436585
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  • Dr. Francine Agbossou-Niedercorn,

    Corresponding author
    1. Unité de Catalyse et de Chimie du Solide, UCCS, CNRS, UMR 8181, Université Lille Nord de France, 59655 Villeneuve d'Ascq (France), Fax: (+33) 320436585
    • Unité de Catalyse et de Chimie du Solide, UCCS, CNRS, UMR 8181, Université Lille Nord de France, 59655 Villeneuve d'Ascq (France), Fax: (+33) 320436585

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  • Dr. Christophe Michon

    Corresponding author
    1. Unité de Catalyse et de Chimie du Solide, UCCS, CNRS, UMR 8181, Université Lille Nord de France, 59655 Villeneuve d'Ascq (France), Fax: (+33) 320436585
    • Unité de Catalyse et de Chimie du Solide, UCCS, CNRS, UMR 8181, Université Lille Nord de France, 59655 Villeneuve d'Ascq (France), Fax: (+33) 320436585

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Abstract

A selected diphosphine binuclear gold(I) chloride complex was combined with a silver salt to catalyze efficiently, for the first time, the asymmetric intramolecular hydroamination of alkenes with high conversions and enantioselectivities, in mild conditions and in presence of water. Both enantiomers of the products could be obtained by controlling the molecular ion-pairs through the solvent polarity. The gold(I) cationic active species was characterized unambiguously at the solid state by X-ray analysis and in solution by DOSY 1H NMR experiments. No contribution of silver chloride was observed on the bonding mode of the catalyst.

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