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

Research output: Contribution to journal › Article

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
Externally published	Yes

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Stereoselectivity

Alkynes

Addition reactions

Stereoisomerism

Temperature

stannane

ASJC Scopus subject areas

Chemistry(all)

Cite this

Shimizu, M., Jiang, G., Murai, M., Takeda, Y., Nakao, Y., Hiyama, T., & Shirakawa, E. (2005). Facile synthesis of trifluoromethyl-substituted enynes: Remarkable reactivity and stereoselectivity of tributyl(3,3,3-trifluoropropynyl)stannane in carbostannylation of alkynes. Chemistry Letters, 34(12), 1700-1701. https://doi.org/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. / 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

Shimizu, M, Jiang, G, Murai, M, Takeda, Y, Nakao, Y, Hiyama, T & Shirakawa, E 2005, 'Facile synthesis of trifluoromethyl-substituted enynes: Remarkable reactivity and stereoselectivity of tributyl(3,3,3-trifluoropropynyl)stannane in carbostannylation of alkynes', Chemistry Letters, vol. 34, no. 12, pp. 1700-1701. https://doi.org/10.1246/cl.2005.1700

Shimizu M, Jiang G, Murai M, Takeda Y, Nakao Y, Hiyama T et al. Facile synthesis of trifluoromethyl-substituted enynes: Remarkable reactivity and stereoselectivity of tributyl(3,3,3-trifluoropropynyl)stannane in carbostannylation of alkynes. Chemistry Letters. 2005 Dec 5;34(12):1700-1701. https://doi.org/10.1246/cl.2005.1700

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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10.1246/cl.2005.1700