The first definitive example of oxidative addition of acyclic vinyl selenide to M(0) complex

The principle of C–S bond activation of acyclic vinlyl sulfide by platinum(0)-complex was applied to the C–Se bond fission of vinyl selenide. The substrate possessing Ph and ArSe (Ar = C6H4Cl-p) substituents at the β-carbon successfully reacted with Pt(0)-complex at 25 °C to produce the vinyl platinum in good yield and its structure was unambiguously determined by X-ray crystallographic analysis. When (Z)-(Me3Si)(ArSe)Cdouble bond; length as m-dash(H)(SeAr) was employed as a reaction substrate, following β-Se elimination took place to liberate Me3SiCCH with the production of [trans-Pt(SeAr)2(PPh3)2]. The oxidative addition of C–Se bond of (E)-(Ph)(H)Cdouble bond; length as m-dashC(H)(SeAr) to Pt(0) was also confirmed at 25 °C, while no C–S bond-breaking occurred when the corresponding vinyl sulfide was exposed to the same reaction conditions, demonstrating that the cleavage of C–Se bond was more facile than that of C–S bond.