A method for the deprotonative silylation of aromatic C-H bonds has been developed using trifluoromethyltrimethylsilane (CFSiMe, Ruppert-Prakash reagent) and a catalytic amount of fluoride. In this reaction, CFSiMe is considered to act as a base and a silicon electrophile. This process is highly tolerant to various functional groups on heteroarenes and benzenes. Furthermore, this method can be applied to the synthesis of trimethylsilyl group-containing analogs of TAC-101, which is a bioactive synthetic retinoid with selective affinity for retinoic acid receptor α (RAR-α) binding. We also report further transformations of the silylated products into useful derivatives.
An S N 2-type trifluoromethylation of benzyl halides under transition-metal-free conditions has been developed using trifluoromethyltrimethylsilane (CF 3 SiMe 3 , Ruppert À Prakash reagent) and CsF in 1,2-dimethoxyethane (DME). Under the developed reaction conditions, the in situ generated trifluoromethyl anion (CF 3 À ) overcame the instability and displayed enhanced nucleophilicity in the presence of DME. This method provides an efficient approach for the generation of various (2,2,2-trifluoroethyl)arenes such as those bearing alkyl, alkoxy, halo (F, Cl, and Br) and trifluoromethyl groups on the benzene rings.
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