On the origin of cine -substitution in the Stille coupling of trisubstituted iodoalkene and trans -vinylstannane

Naoki Kanoh; Yutaro Ohno; Tomohiro Itagaki; Hayato Fukuda; Yoshiharu Iwabuchi

doi:10.1055/s-0033-1339899

On the origin of cine -substitution in the Stille coupling of trisubstituted iodoalkene and trans -vinylstannane

Naoki Kanoh, Yutaro Ohno, Tomohiro Itagaki, Hayato Fukuda, Yoshiharu Iwabuchi

PHA - Molecular Pharmaceutical Science

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

1 Citation (Scopus)

Abstract

Factors determining the course of reaction (i.e., usual coupling vs. abnormal cine-substitution) in the Stille coupling of trisubstituted iodoalkene and trans-vinylstannane were investigated. The palladium-catalyzed reaction with triphenylarsine and lithium chloride in N-methylpyrrolidone gave the normal Stille coupling product in good yield and good selectivity, while the use of N,N-diisopropylethylamine and cuprous iodide in toluene afforded the cine-substituted product exclusively. It is proposed that transmetalation between vinylpalladium and vinylstannane species determines the course of reaction.

Original language	English
Article number	ST-2013-U0685-L
Pages (from-to)	2660-2664
Number of pages	5
Journal	Synlett
Volume	24
Issue number	20
DOIs	https://doi.org/10.1055/s-0033-1339899
Publication status	Published - 2013 Dec 17

Keywords

Stille reaction
alkenes
cross-coupling
palladium
regioselectivity

ASJC Scopus subject areas

Organic Chemistry

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10.1055/s-0033-1339899

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abstract = "Factors determining the course of reaction (i.e., usual coupling vs. abnormal cine-substitution) in the Stille coupling of trisubstituted iodoalkene and trans-vinylstannane were investigated. The palladium-catalyzed reaction with triphenylarsine and lithium chloride in N-methylpyrrolidone gave the normal Stille coupling product in good yield and good selectivity, while the use of N,N-diisopropylethylamine and cuprous iodide in toluene afforded the cine-substituted product exclusively. It is proposed that transmetalation between vinylpalladium and vinylstannane species determines the course of reaction.",

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AU - Kanoh, Naoki

AU - Ohno, Yutaro

AU - Itagaki, Tomohiro

AU - Fukuda, Hayato

AU - Iwabuchi, Yoshiharu

PY - 2013/12/17

Y1 - 2013/12/17

N2 - Factors determining the course of reaction (i.e., usual coupling vs. abnormal cine-substitution) in the Stille coupling of trisubstituted iodoalkene and trans-vinylstannane were investigated. The palladium-catalyzed reaction with triphenylarsine and lithium chloride in N-methylpyrrolidone gave the normal Stille coupling product in good yield and good selectivity, while the use of N,N-diisopropylethylamine and cuprous iodide in toluene afforded the cine-substituted product exclusively. It is proposed that transmetalation between vinylpalladium and vinylstannane species determines the course of reaction.

AB - Factors determining the course of reaction (i.e., usual coupling vs. abnormal cine-substitution) in the Stille coupling of trisubstituted iodoalkene and trans-vinylstannane were investigated. The palladium-catalyzed reaction with triphenylarsine and lithium chloride in N-methylpyrrolidone gave the normal Stille coupling product in good yield and good selectivity, while the use of N,N-diisopropylethylamine and cuprous iodide in toluene afforded the cine-substituted product exclusively. It is proposed that transmetalation between vinylpalladium and vinylstannane species determines the course of reaction.

KW - Stille reaction

KW - alkenes

KW - cross-coupling

KW - palladium

KW - regioselectivity

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On the origin of cine -substitution in the Stille coupling of trisubstituted iodoalkene and trans -vinylstannane

Abstract

Keywords

ASJC Scopus subject areas

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