A practical synthesis and applications of (E)-diphenyl-β- (trifluoromethyl)vinylsulfonium triflate

Noritaka Kasai, Ryoko Maeda, Hiroshi Furuno, Takeshi Hanamoto

    研究成果: Contribution to journalArticle査読

    23 被引用数 (Scopus)

    抄録

    (E)-Diphenyl-β-(trifluoromethyl)vinylsulfonium triflate, readily prepared from 2-bromo-3,3,3-trifluoroprop-1-ene in two steps, undergoes double alkylation with active methylene compounds in dimethyl sulfoxide or ethyl acetate, in an open vessel at room temperature, to provide the corresponding trifluoromethylated cyclopropane derivatives in excellent yields. The cyclopropane, ethyl 1-cyano-2-(trifluoromethyl)cyclopropanecarboxylate is subjected to a ring-opening reaction followed by cyclization to afford a trifluoromethylated dihydroaminothiophene, which on oxidation with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone furnishes the corresponding trifluoromethylated aminothiophene in a high 88% yield.

    本文言語英語
    論文番号SS-2012-F0636-OP
    ページ(範囲)3489-3495
    ページ数7
    ジャーナルSynthesis (Germany)
    44
    22
    DOI
    出版ステータス出版済み - 2012

    All Science Journal Classification (ASJC) codes

    • 触媒
    • 有機化学

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