Pd-Catalyzed C(sp3)–C(sp2) cross-coupling of Y(CH2SiMe3)3(THF)2 with vinyl bromides and triflates

Abstract

Pd-Catalyzed C(sp³)–C(sp²) cross-coupling of Y(CH₂SiMe₃)₃(THF)₂ with vinyl bromides and triflates has been developed for efficient synthesis of various allyltrimethylsilanes. The cross-coupling reaction was conducted at room temperature with low catalyst loading of either Pd(PPh₃)₄ or Pd(PPh₃)₂Cl₂, and exhibited high efficiency and a broad substrate scope. In combination with the cross-coupling by the Lewis-acid catalyzed Hosomi–Sakurai reaction, a novel three-component one-pot cascade reaction was then accomplished to deliver homoallylic alcohols and ethers with high regioselectivity and diastereoselectivity. The three-component reaction defined the yttrium complex as a novel one-carbon synthon, which could either trigger bifunctionalization of alkenes or link two electrophiles and would find applications in organic synthesis.