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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