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

Abstract : 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.
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https://hal-normandie-univ.archives-ouvertes.fr/hal-02046303
Contributor : Madeleine Roux-Merlin <>
Submitted on : Friday, February 22, 2019 - 3:40:16 PM
Last modification on : Thursday, July 2, 2020 - 3:28:49 AM

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Kanako Nozawa-Kumada, Sayuri Osawa, Midori Sasaki, Isabelle Chataigner, Masanori Shigeno, et al.. Deprotonative Silylation of Aromatic C-H Bonds Mediated by a Combination of Trifluoromethyltrialkylsilane and Fluoride. Journal of Organic Chemistry, American Chemical Society, 2017, 82 (18), pp.9487-9496. ⟨10.1021/acs.joc.7b01525⟩. ⟨hal-02046303⟩

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