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)C(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)CC(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.

Graphical abstractThe principle of C–S bond activation of acyclic vinlyl sulfide by platinum(0)-complex was successfully applicable to the C–Se bond fission of vinyl selenide to produce vinyl platinum.Figure optionsDownload full-size imageDownload as PowerPoint slide