27602-36-4

Upstream product

• 28314-80-9 2,4,6-trifluorobenzoic acid 
• 1192454-96-8 tert-butyl 2,4,6-trifluorobenzoate 
• 372-38-3 1,3,5-trifluorobenzene 
• 51584-53-3 (2,4,6-trifluorophenyl)trimethylsilane 
• 124-38-9 carbon dioxide 
• 27602-30-8 2,4,6-trifluoro-1,3-benzenediyl-1,3-bis(trimethylsilane) 

Relevant academic research and scientific papers

Deprotonative Silylation of Aromatic C-H Bonds Mediated by a Combination of Trifluoromethyltrialkylsilane and Fluoride

A method for the deprotonative silylation of aromatic C-H bonds has been developed using trifluoromethyltrimethylsilane (CF3SiMe3, Ruppert-Prakash reagent) and a catalytic amount of fluoride. In this reaction, CF3SiMe3 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.

Remote trimethylsilyl groups interfering with the ortho deprotonation of fluoroarenes and chloroarenes

(2-Fluorophenyl)trimethylsilane (2-F) and (2-chlorophenyl)-trimethylsilane (2-Cl) react with sec-butyllithium or lithium 2,2,6,6-tetramethylpiperidide under permutational hydrogen/metal interconversion (metalation) more slowly than, respectively, the corr