Zinc-Mediated Formation of Trifluoromethyl Ethers from Alcohols and Hypervalent Iodine Trifluoromethylation Reagents

Authors

  • Raffael Koller,

    1. Department of Chemistry and Applied Biosciences, Swiss Federal Institute of Technology, ETH Zürich, 8093 Zürich (Switzerland), Fax: (+41) 44-632-1310
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  • Kyrill Stanek,

    1. Department of Chemistry and Applied Biosciences, Swiss Federal Institute of Technology, ETH Zürich, 8093 Zürich (Switzerland), Fax: (+41) 44-632-1310
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  • Daniel Stolz Dr.,

    1. Department of Chemistry and Applied Biosciences, Swiss Federal Institute of Technology, ETH Zürich, 8093 Zürich (Switzerland), Fax: (+41) 44-632-1310
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  • Raphael Aardoom,

    1. Department of Chemistry and Applied Biosciences, Swiss Federal Institute of Technology, ETH Zürich, 8093 Zürich (Switzerland), Fax: (+41) 44-632-1310
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    • R. Aardoom and K. Niedermann carried out the X-ray crystal structural study of compound 5.

  • Katrin Niedermann,

    1. Department of Chemistry and Applied Biosciences, Swiss Federal Institute of Technology, ETH Zürich, 8093 Zürich (Switzerland), Fax: (+41) 44-632-1310
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    • R. Aardoom and K. Niedermann carried out the X-ray crystal structural study of compound 5.

  • Antonio Togni Prof. Dr.

    1. Department of Chemistry and Applied Biosciences, Swiss Federal Institute of Technology, ETH Zürich, 8093 Zürich (Switzerland), Fax: (+41) 44-632-1310
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  • This work was supported by SSCI (Stipendienfonds der Schweizerischen Chemischen Industrie), ETH Zürich, and DAAD. Dr. H. Rüegger and A. Moreno are acknowledged for their help with NMR spectroscopy.

Abstract

Schieb mal rüber: Der Transfer einer intakten Trifluormethylgruppe von einem hypervalenten Iodreagens zu einem aliphatischen Alkohol verläuft glatt bei einer Aktivierung durch Zinkbis(triflimid). Dies ist eine einfache Methode zur Synthese von Trifluormethoxyalkyl-Derivaten, die sonst nur schwer zugänglich sind.

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