Transition-Metal-Free Trifluoromethylation of Benzyl Bromides Using Trifluoromethyltrimethylsilane and CsF in 1,2-Dimethoxyethane

Kanako Nozawa-Kumada, Sayuri Osawa, Takuto Ojima, Koto Noguchi, Masanori Shigeno, Yoshinori Kondo

Research output: Contribution to journalArticle

Abstract

An SN2-type trifluoromethylation of benzyl halides under transition-metal-free conditions has been developed using trifluoromethyltrimethylsilane (CF3SiMe3, Ruppert−Prakash reagent) and CsF in 1,2-dimethoxyethane (DME). Under the developed reaction conditions, the in situ generated trifluoromethyl anion (CF3 ) overcame the instability and displayed enhanced nucleophilicity in the presence of DME. This method provides an efficient approach for the generation of various (2,2,2-trifluoroethyl)arenes such as those bearing alkyl, alkoxy, halo (F, Cl, and Br) and trifluoromethyl groups on the benzene rings.

Original languageEnglish
Pages (from-to)765-768
Number of pages4
JournalAsian Journal of Organic Chemistry
Volume9
Issue number5
DOIs
Publication statusPublished - 2020 May 1

Keywords

  • (2,2,2-trifluoroethyl)arenes
  • Ruppert-Prakash reagent
  • benzyl halides
  • transition-metal-free
  • trifluoromethylation

ASJC Scopus subject areas

  • Organic Chemistry

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