Palladium-Catalyzed Reaction of Propargylic Carbonates with Benzyne

Abstract

Under the catalysis of palladium acetate, 1,2-allenyl­palladium formed from propargylic carbonates may react with two molecules of benzyne to afford phenanthrene derivatives by cyclization and β-H elimination.

Key words

propargylic carbonates - allenylpalladium - phen­anthrene derivatives - cyclization - β-H elimination

• References and Notes

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• 6 Crystal Data for Compound 3f C₂₃H₁₈, MW = 294.14, monoclinic, space group P₂ (1), final R indices [I > 2σ(I)], R ₁ = 0.0472, wR ₂ = 0.1223, R indices (all data), R ₁ = 0.0593, wR ₂ = 0.1310, a = 6.2434(5) Å, b = 8.0127(7) Å, c = 21.1301(18) Å, α = 90^o, β = 90.262(2)^o, γ = 90^o, V = 1057.05(15) ų, T = 293 (2) K, Z = 2, reflections collected/unique: 6377/4106 [R(int) = 0.0195], number of observations [>2σ(I)] 3264; parameter: 256. Supplementary crystallographic data have been deposited at the Cambridge Crystallographic Data Center (CCDC 941026).