Preparation of trifluoromethyl and other perfluoroalkyl compounds with (perfluoroalkyl)trimethylsilanes

TLDR: In this article, a variety of novel perfluoroalkyl-substituted compounds in high yields using easily prepared (perfluoralkyl)trimethylsilanes (1a-c) is described.

Abstract: The preparation of a variety of novel perfluoroalkyl-substituted compounds in high yields using easily prepared (perfluoroalkyl)trimethylsilanes (1a-c) is described. (Trifluoromethyl)-, (pentafluoroethyl)-, and (heptafluoropropyl)trimethylsilane, 1a-c, respectively, react readily with carbonyl compounds, such as aldehydes and ketones, by a fluoride-initiated catalytic process. Fluoride-initiated addition of 1 to a carbonyl group generates an oxyanionic species which then further catalyzes the reaction. Even enolizable carbonyl compounds react cleanly under the reaction conditions. A study of the scope of the reactivity of 1a toward other carbonyl groups in esters, lactones and an acid chloride was also carried out