Facile synthesis of trifluoromethyl-substituted enynes: Remarkable reactivity and stereoselectivity of tributyl(3,3,3-trifluoropropynyl)stannane in carbostannylation of alkynes

Masaki Shimizu, Guofang Jiang, Masahito Murai, Youhei Takeda, Yoshiaki Nakao, Tamejiro Hiyama, Eiji Shirakawa

Research output: Contribution to journalArticle

15 Citations (Scopus)

Abstract

Carbostannylation of alkynes with tributyl(3,3,3-trifluoropropynyl)stannane is found to proceed at room temperature in a syn-manner, giving rise to the corresponding CF3-substituted enynes as a single stereoisomer in good yields. Both terminal and, CF3- or RO2C-substituted internal alkynes are applicable to the addition reaction. Synthetic applications of the adduct are also demonstrated.

Original languageEnglish
Pages (from-to)1700-1701
Number of pages2
JournalChemistry Letters
Volume34
Issue number12
DOIs
Publication statusPublished - Dec 5 2005
Externally publishedYes

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Stereoselectivity
Alkynes
Addition reactions
Stereoisomerism
Temperature
stannane

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Facile synthesis of trifluoromethyl-substituted enynes : Remarkable reactivity and stereoselectivity of tributyl(3,3,3-trifluoropropynyl)stannane in carbostannylation of alkynes. / Shimizu, Masaki; Jiang, Guofang; Murai, Masahito; Takeda, Youhei; Nakao, Yoshiaki; Hiyama, Tamejiro; Shirakawa, Eiji.

In: Chemistry Letters, Vol. 34, No. 12, 05.12.2005, p. 1700-1701.

Research output: Contribution to journalArticle

Shimizu, Masaki ; Jiang, Guofang ; Murai, Masahito ; Takeda, Youhei ; Nakao, Yoshiaki ; Hiyama, Tamejiro ; Shirakawa, Eiji. / Facile synthesis of trifluoromethyl-substituted enynes : Remarkable reactivity and stereoselectivity of tributyl(3,3,3-trifluoropropynyl)stannane in carbostannylation of alkynes. In: Chemistry Letters. 2005 ; Vol. 34, No. 12. pp. 1700-1701.
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