A Practical Synthesis and Applications of (E)-Diphenyl-β-(trifluoromethyl)vinylsulfonium Triflate

Noritaka Kasai; Ryoko Maeda; Hiroshi Furuno; Takeshi Hanamoto

doi:10.1055/s-0032-1316792

Synthesis, Table of Contents

Synthesis 2012; 44(22): 3489-3495
DOI: 10.1055/s-0032-1316792

paper

A Practical Synthesis and Applications of (E)-Diphenyl-β-(trifluoromethyl)vinylsulfonium Triflate

Authors

Noritaka Kasai

^aDepartment of Chemistry and Applied Chemistry, Graduate School of Science and Engineering, Saga University, Honjo-machi, Saga 840-8502, Japan
Ryoko Maeda

^aDepartment of Chemistry and Applied Chemistry, Graduate School of Science and Engineering, Saga University, Honjo-machi, Saga 840-8502, Japan
Hiroshi Furuno

^bInstitute for Materials Chemistry and Engineering (IMCE), Kyushu University, Hakozaki, Higashi-ku, Fukuoka 812-8581, Japan Fax: +81(952)288548 Email: hanamoto@cc.saga-u.ac.jp
Takeshi Hanamoto*

^aDepartment of Chemistry and Applied Chemistry, Graduate School of Science and Engineering, Saga University, Honjo-machi, Saga 840-8502, Japan

Abstract

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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.

Key words

vinylsulfonium salts - heterocycles - cyclization - fluorine - ylides

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References

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