Synthesis 2012; 44(22): 3489-3495
DOI: 10.1055/s-0032-1316792
paper
© Georg Thieme Verlag Stuttgart · New York

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

Noritaka Kasai
a  Department of Chemistry and Applied Chemistry, Graduate School of Science and Engineering, Saga University, Honjo-machi, Saga 840-8502, Japan
,
Ryoko Maeda
a  Department of Chemistry and Applied Chemistry, Graduate School of Science and Engineering, Saga University, Honjo-machi, Saga 840-8502, Japan
,
Hiroshi Furuno
b  Institute 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*
a  Department of Chemistry and Applied Chemistry, Graduate School of Science and Engineering, Saga University, Honjo-machi, Saga 840-8502, Japan
› Author Affiliations
Further Information

Publication History

Received: 02 August 2012

Accepted after revision: 10 September 2012

Publication Date:
27 September 2012 (online)


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.

 
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