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A Ritter-Type Reaction: Direct Electrophilic Trifluoromethylation at Nitrogen Atoms Using Hypervalent Iodine Reagents

Authors

  • Katrin Niedermann,

    1. Department Chemie und Angewandte Biowissenschaften, Eidgenössische Technische Hochschule (ETH) Zürich, Wolfgang-Pauli-Strasse 10, 8093 Zürich (Schweiz), Fax: (+41) 44-632-1310
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  • Natalja Früh,

    1. Department Chemie und Angewandte Biowissenschaften, Eidgenössische Technische Hochschule (ETH) Zürich, Wolfgang-Pauli-Strasse 10, 8093 Zürich (Schweiz), Fax: (+41) 44-632-1310
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  • Ekaterina Vinogradova,

    1. Department Chemie und Angewandte Biowissenschaften, Eidgenössische Technische Hochschule (ETH) Zürich, Wolfgang-Pauli-Strasse 10, 8093 Zürich (Schweiz), Fax: (+41) 44-632-1310
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  • Dr. Matthias S. Wiehn,

    1. Department Chemie und Angewandte Biowissenschaften, Eidgenössische Technische Hochschule (ETH) Zürich, Wolfgang-Pauli-Strasse 10, 8093 Zürich (Schweiz), Fax: (+41) 44-632-1310
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  • Dr. Aitor Moreno,

    1. Department Chemie und Angewandte Biowissenschaften, Eidgenössische Technische Hochschule (ETH) Zürich, Wolfgang-Pauli-Strasse 10, 8093 Zürich (Schweiz), Fax: (+41) 44-632-1310
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  • Prof. Dr. Antonio Togni

    Corresponding author
    1. Department Chemie und Angewandte Biowissenschaften, Eidgenössische Technische Hochschule (ETH) Zürich, Wolfgang-Pauli-Strasse 10, 8093 Zürich (Schweiz), Fax: (+41) 44-632-1310
    • Department Chemie und Angewandte Biowissenschaften, Eidgenössische Technische Hochschule (ETH) Zürich, Wolfgang-Pauli-Strasse 10, 8093 Zürich (Schweiz), Fax: (+41) 44-632-1310
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  • This work was supported by the ETH Zürich. M.S.W. thanks the Karlsruhe House of Young Scientists for a fellowship. We thank Dr. J. Welch for his help with the kinetic studies and R. Koller for helpful discussions and advice.

Abstract

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Acid-catalyzed electrophilic trifluoromethylation of nitriles in the presence of azoles leads to N-(trifluoromethyl)imine derivatives. The source of the trifluoromethyl group is a readily prepared and easy-to-handle hypervalent iodine(III) reagent (see scheme; HNTf2=bis(N-(trifluoromethanesulfonyl)imide). This Ritter-type reaction is astraightforward approach to N-(trifluoromethyl)imidoyl azoles, compounds otherwise very difficult to access.

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