N-Acyliminium Ion Chemistry: Highly Efficient and Versatile Carbon–Carbon Bond Formation by Nucleophilic Substitution of Hydroxy Groups Catalyzed by Sn(NTf2)4

Authors

  • Raja Ben Othman Dr.,

    1. URCOM, EA 3221, FR 3038, Faculté des Sciences et Techniques de l'Université du Havre, 25, Rue Philippe Lebon, BP 540, 76058 Le Havre (France), Fax: (+33) 2-3274-4391
    2. Present address: Unité de recherche en Matériaux, Energie et Environnement (MEE), Université de Gafsa, Sidi Ahmed Zarrouk, Gafsa, 2112 (Tunisie)
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  • Radouane Affani Dr.,

    1. URCOM, EA 3221, FR 3038, Faculté des Sciences et Techniques de l'Université du Havre, 25, Rue Philippe Lebon, BP 540, 76058 Le Havre (France), Fax: (+33) 2-3274-4391
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  • Marie-José Tranchant,

    1. URCOM, EA 3221, FR 3038, Faculté des Sciences et Techniques de l'Université du Havre, 25, Rue Philippe Lebon, BP 540, 76058 Le Havre (France), Fax: (+33) 2-3274-4391
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  • Sylvain Antoniotti Dr.,

    1. LCMBA. UMR 6001, Université de Nice-Sophia Antipolis, C.N.R.S. Institut de Chimie de Nice, 28, avenue de Valrose, 06108 Nice (France), Fax: (+33) 4-9207-6125
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  • Vincent Dalla Prof.,

    1. URCOM, EA 3221, FR 3038, Faculté des Sciences et Techniques de l'Université du Havre, 25, Rue Philippe Lebon, BP 540, 76058 Le Havre (France), Fax: (+33) 2-3274-4391
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  • Elisabet Duñach Dr.

    1. LCMBA. UMR 6001, Université de Nice-Sophia Antipolis, C.N.R.S. Institut de Chimie de Nice, 28, avenue de Valrose, 06108 Nice (France), Fax: (+33) 4-9207-6125
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Abstract

original image

Atom-economical: Unmodified hemi-N,O-acetals are used in a catalytic, highly efficient α-amidoalkylation of a broad range of carbon-centered nucleophiles, including silicon-based components, active methylene derivatives, electron-rich arenes, and even simple ketones (see scheme). The reactions proceed in a highly efficient manner and typically require only 1 mol % of the Lewis superacidic reagent Sn(NTf2)4 as the catalyst.

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