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

Research output: Contribution to journalArticlepeer-review

10 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)9487-9496
Number of pages10
JournalJournal of Organic Chemistry
Volume82
Issue number18
DOIs
Publication statusPublished - 2017 Sep 15

ASJC Scopus subject areas

  • Organic Chemistry

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