133117-48-3Relevant articles and documents
Deprotonative Silylation of Aromatic C-H Bonds Mediated by a Combination of Trifluoromethyltrialkylsilane and Fluoride
Nozawa-Kumada, Kanako,Osawa, Sayuri,Sasaki, Midori,Chataigner, Isabelle,Shigeno, Masanori,Kondo, Yoshinori
, p. 9487 - 9496 (2017/09/23)
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.
Synthetic applications of fluorinated phenyllithiums: Preparation of fluorinated α-methylstyrenes, benzhydrols, benzophenones and aryltrimethylsilanes
Yarwood, Thomas David,Waring, Anthony John,Coe, Paul Leslie
, p. 113 - 119 (2007/10/03)
Regioselective preparations of a number of fluorinated phenyllithiums have recently been reported, which in some cases also contain one or more bromine substituents. These have now been applied to the synthesis of the corresponding halogenated 2-arylpropenes (α-methyl-styrenes), benzhydrols, trifluoromethylbenzhydrols, benzophenones and aryltrimethylsilanes.