On the Origin of cine-Substitution in the Stille Coupling of Trisubstituted Iodoalkene and trans-Vinylstannane

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.

Key words

Stille reaction - cross-coupling - palladium - regioselectivity - alkenes

• References

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