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

Noritaka Kasai, Ryoko Maeda, Hiroshi Furuno, Takeshi Hanamoto

    Research output: Contribution to journalArticlepeer-review

    20 Citations (Scopus)

    Abstract

    (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.

    Original languageEnglish
    Article numberSS-2012-F0636-OP
    Pages (from-to)3489-3495
    Number of pages7
    JournalSynthesis (Germany)
    Volume44
    Issue number22
    DOIs
    Publication statusPublished - 2012

    All Science Journal Classification (ASJC) codes

    • Catalysis
    • Organic Chemistry

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