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18.15.1.2.4 Method 4: Synthesis of Trimethyl(trifluoromethyl)silane (Ruppert's Reagent)

DOI: 10.1055/sos-SD-018-01314

Il'chenko, A. Y.Science of Synthesis, (2005181143.

Trimethyl(trifluoromethyl)silane (25) (bp 45°C) is a reagent that can be used for the introduction of the trifluoromethyl group under mild conditions.[‌78‌‌80‌] It can be prepared from bromotrifluoromethane (5), hexaethylphosphorous triamide, and chlorotrimethylsilane (Scheme 16);[‌78‌,‌79‌] from trifluoroiodomethane (9), tetrakis(dimethylamino)ethene, and chlorotrimethylsilane (Scheme 16);[‌78‌] or from bromotrifluoromethane (5), chlorotrimethylsilane, and aluminum (Scheme 16).[‌81‌] The use of trimethyl(trifluoromethyl)silane (25) in the trifluoromethylation of a carbonyl compound in the presence of the fluoride ion is illustrated in Scheme 16.[‌78‌]

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