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Deprotonative Silylation of Aromatic C–H Bonds Mediated by a Combination of Trifluoromethyltrialkylsilane and Fluoride
journal contribution
posted on 2017-08-15, 00:00 authored by Kanako Nozawa-Kumada, Sayuri Osawa, Midori Sasaki, Isabelle Chataigner, Masanori Shigeno, Yoshinori KondoA 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.
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benzenederivativeretinoic acid receptor αbindingtrimethylsilyl group-containing analogsAromaticheteroareneMediatedCombinationDeprotonative SilylationtrifluoromethyltrimethylsilaneTACaffinitybioactivemethodsynthesissilylated productsretinoidsilicon electrophilereagentTrifluoromethyltrialkylsilaneFluoridetransformationBondCF 3 SiMe 3RARdeprotonative silylationRuppertfluoridebond
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