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

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  • Kanako Nozawa‐Kumada
    Graduate School of Pharmaceutical Sciences Tohoku University 6-3 Aoba, Aramaki, Aoba-ku Sendai 980-8578 Japan
  • Sayuri Osawa
    Graduate School of Pharmaceutical Sciences Tohoku University 6-3 Aoba, Aramaki, Aoba-ku Sendai 980-8578 Japan
  • Takuto Ojima
    Graduate School of Pharmaceutical Sciences Tohoku University 6-3 Aoba, Aramaki, Aoba-ku Sendai 980-8578 Japan
  • Koto Noguchi
    Graduate School of Pharmaceutical Sciences Tohoku University 6-3 Aoba, Aramaki, Aoba-ku Sendai 980-8578 Japan
  • Masanori Shigeno
    Graduate School of Pharmaceutical Sciences Tohoku University 6-3 Aoba, Aramaki, Aoba-ku Sendai 980-8578 Japan
  • Yoshinori Kondo
    Graduate School of Pharmaceutical Sciences Tohoku University 6-3 Aoba, Aramaki, Aoba-ku Sendai 980-8578 Japan

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<jats:title>Abstract</jats:title><jats:p>An S<jats:sub>N</jats:sub>2‐type trifluoromethylation of benzyl halides under transition‐metal‐free conditions has been developed using trifluoromethyltrimethylsilane (CF<jats:sub>3</jats:sub>SiMe<jats:sub>3</jats:sub>, Ruppert−Prakash reagent) and CsF in 1,2‐dimethoxyethane (DME). Under the developed reaction conditions, the in situ generated trifluoromethyl anion (CF<jats:sub>3</jats:sub><jats:sup>−</jats:sup>) 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.</jats:p>

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