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

Kanako Nozawa-Kumada, Sayuri Osawa, Midori Sasaki, Isabelle Chataigner, Masanori Shigeno, Yoshinori Kondo

研究成果: ジャーナルへの寄稿学術論文査読

16 被引用数 (Scopus)

抄録

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.

本文言語英語
ページ(範囲)9487-9496
ページ数10
ジャーナルJournal of Organic Chemistry
82
18
DOI
出版ステータス出版済み - 2017 9月 15

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