Trifluoromethyltrimethylsilane

[4] In the presence of a metal salt (M+ X−), the reagent reacts with aldehydes and ketones to give a trimethylsilyl ether, the net product of insertion of the carbonyl into the Si-CF3 bond.

A typical initiator is a soluble fluoride-containing species such as tetrabutylammonium fluoride; however, simple alkoxides such as KOtBu are also effective.

This -ate complex is unable to react directly with the carbonyl, resulting in powerful inhibition of the chain reaction by the reagent.

This inhibitory process is common to all anion-initiated reactions of the reagent, with the identity of the counter-cation (M+) playing a major role in controlling the overall rate.

[6] The reagent has largely supplanted trifluoromethyllithium, which is not isolable and rapidly decomposes to yield lithium fluoride and difluorocarbene.

Skeletal formula of trifluoromethyltrimethylsilane
Ball-and-stick model of the trifluoromethyltrimethylsilane molecule