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

Noritaka Kasai, Ryoko Maeda, Hiroshi Furuno, Takeshi Hanamoto

Research output: Contribution to journalArticle

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
Volume44
Issue number22
DOIs
Publication statusPublished - 2012

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Dimethyl sulfoxide
Cyclization
Alkylation
Derivatives
Oxidation
Dimethyl Sulfoxide
Temperature
diphenyl
cyclopropane
dichlorodicyanobenzoquinone
ethyl acetate

All Science Journal Classification (ASJC) codes

  • Organic Chemistry
  • Catalysis

Cite this

A practical synthesis and applications of (E)-diphenyl-β- (trifluoromethyl)vinylsulfonium triflate. / Kasai, Noritaka; Maeda, Ryoko; Furuno, Hiroshi; Hanamoto, Takeshi.

In: Synthesis, Vol. 44, No. 22, SS-2012-F0636-OP, 2012, p. 3489-3495.

Research output: Contribution to journalArticle

Kasai, Noritaka ; Maeda, Ryoko ; Furuno, Hiroshi ; Hanamoto, Takeshi. / A practical synthesis and applications of (E)-diphenyl-β- (trifluoromethyl)vinylsulfonium triflate. In: Synthesis. 2012 ; Vol. 44, No. 22. pp. 3489-3495.
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AB - (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.

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