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

doi:10.1246/cl.2005.1700

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

Graduate School of Natural Science and Technology

Research output: Contribution to journal › Article › peer-review

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 language	English
Pages (from-to)	1700-1701
Number of pages	2
Journal	Chemistry Letters
Volume	34
Issue number	12
DOIs	https://doi.org/10.1246/cl.2005.1700
Publication status	Published - Dec 5 2005

ASJC Scopus subject areas

Chemistry(all)

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10.1246/cl.2005.1700

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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 journal › Article › peer-review

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AU - Takeda, Youhei

AU - Nakao, Yoshiaki

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AU - Shirakawa, Eiji

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