Pd-Catalyzed C(sp3)-C(sp2) cross-coupling of Y(CH2SiMe3)3(THF)2 with vinyl bromides and triflates
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.
Trifluoromethylation of allylsilanes under copper catalysis
Branched allylic CF3 products are accessible by copper-catalyzed trifluoromethylation of allylsilanes with the Togni reagent I. The silyl group is critical to control the outcome of this reaction because in its absence, a product of addition be
Chemoselective Synthesis of Allyltrimethylsilanes by Cross-Coupling of Vinyl Triflates with Tris((trimethylsilyl)methyl)aluminum Catalyzed by Palladium(0)
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Saulnier, Mark G.,Kadow, John F.,Tun, Min Min,Langley, David R.,Vyas, Dolatrai M.
p. 8320 - 8321
(2007/10/02)
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