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Synlett 1996; 1996(2): 151-153
DOI: 10.1055/s-1996-5355
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Facile Preparation of (Trifluoromethyl)tributyltin and Transtrifluoromethylation of Disilyl Sulfides to the Corresponding Trifluoromethylsilanes1

G. K. Surya Prakash* , Andrei K. Yudin, Denis Deffieux, George A. Olah1
  • *Donald P. and Katherine B. Loker Hydrocarbon Research Institute and Department of Chemistry, University of Southern California, University Park, Los Angeles, CA 90089-1661
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Publikationsdatum:
31. Dezember 2000 (online)

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(Trifluoromethyl)trimethylsilane (Me3SiCF3) was converted to (trifluoromethyl)tributyltin (Bu3SnCF3, 1) in quantitative yield by treatment with bis(tributyltin) oxide in tetrahydrofuran under fluoride ion initiation. Bu3SnCF3 was found to readily trifluoromethylate disilyl sulfides at room temperature giving the corresponding trifluoromethylated di- and trialkylsilanes in high yields. This method provides a new approach for the preparation of silicon-based trifluoromethylating reagents via transtrifluoromethylation of compounds containing Si-S bonds.

Transtrifluoromethylation - (trifluoromethyl)tributyltin - trifluoromethylsilanes