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Synthesis of β-Boryl-α,β-unsaturated Carbonyl Compounds via Palladium-Catalyzed Cross-Coupling Reaction of Bis(pinacolato)diboron with Vinyl Triflates

Jun Takagi, Akihiro Kamon, Tatsuo Ishiyama*, Norio Miyaura

*Division of Molecular Chemistry, Graduate School of Engineering, Hokkaido University, Sapporo 060-8628, Japan,

J. Takagi, A. Kamon, T. Ishiyama, N. Miyaura, Synlett., 2002, 1880-1882.

DOI: 10.1055/s-2002-34869

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The Cross-coupling reaction of bis(pinacolato)diboron with β-(trifluoromethanesulfonyloxy)-α,β-unsaturated carbonyl compounds was carried out in the presence of PdCl2(PPh3)2-2PPh3 (3 mol%) and KOPh in toluene or K2CO3 in dioxane for the synthesis of cyclic and acyclic β-boryl-α,β-unsaturated esters, amides, and ketones in high yields.

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Key Words

Miyaura Reaction, diboron, vinyl triflate, palladium, cross-coupling, catalysis, vinylboronates

ID: J60-Y2002-930