Preparation of the trifluoromethyltrimethylsilane was reported by Ingo Ruppert in 1984. In 1989, Prakash and Olah first reported activation of TMSCF by fluoride to perform nucleophilic trifluoromethylation of carbonyl compounds. In the same year, Stahly described similar reactions for the synthesis of trifluoromethylated phenols and anilines. Since then TMSCF has been widely used as a nucleophilic trifluoromethylating agent.
An example is the trifluoromethylation of cyclohexanone in THF using tetrabutylammonium fluoride.
The substrates can be aryl halides. Potassium (trifluoromethyl)trimethoxyborate for this purpose has been synthesised from B(OMe), CFSiMe and KF. Aryl functionalization by C-H activation has also been reported.