DABCO-Catalyzed Reaction of Phenols or 1,2-Diphenols with Activated Alkynes Leading to the Formation of Alkenoic Acid Esters or 1,3-Dioxole Derivatives

Abstract

The reaction of phenols or 1,2-diphenols with activated alkynes took place smoothly and rapidly in the presence of a catalytic amount of 1,4-diazabicyclo[2.2.2]octane (DABCO) at room temperature and resulted in the formation of various alkenoic acid esters or 1,3-dioxole derivatives in excellent yields. The scope and limitations, together with a plausible mechanism of the reaction are disclosed in this paper.

phenoles - 1,2-diphenoles - activated alkynes - alkenoic acid esters - 1,3-dioxoles

References

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10

Crystal data of 3 have been deposited in CCDC as deposition number 295601: C₁₄H₁₄O₆, MW = 278.25, T = 296 (2) K, λ = 0.71073 Å, Monoclinic space group P2(1)/c, a = 10.046 (2) Å, b = 18.482 (4) Å, c = 7.566 (1) Å, α = 90.00°, β = 95.32 (2)°, γ = 90.00°, V = 1398.7 (5) ų, Z = 4, D _c = 1.321 mg/m³, µ = 0.104 mm^-1, F(000) = 584, Crystal size 0.58 × 0.52 × 0.50 mm, Independent reflections 2600 [R(int) = 0.0103], Reflections collected 3009, Refinement method, full-matrix least-squares on F ², Goodness-of-fit on F ² 1.083, Final R indices [I > 2σ(I)] R1 = 0.0387, wR2 = 0.1116, R indices (all data) R1 = 0.0627, wR2 = 0.1197, Extinction coefficient 0.119 (6), Largest diff. peak and hole 0.233 and -0.166 eÅ^-3.

11 Nozaki K. Sato N. Ikeda K. Takaya H. J. Org. Chem.  1996,  61:  4516 

12

Crystal data of 15 have been deposited in CCDC as deposition number 295602: C₁₂H₁₂O₆, MW = 252.22, T = 296 (2) K, λ = 0.71073 Å, Orthorhombic space group Pbca, a = 7.314 (1) Å, b = 17.931 (4) Å, c = 18.351 (5) Å, α = 90.00°, β = 90.00°, γ = 90.00°, V = 2406.52 (67) ų, Z = 8, D _c = 1.392 mg/m³, µ = 0.113 mm^-1, F(000) = 1056, Crystal size 0.60 × 0.34 × 0.34 mm, Independent reflections 2769 [R(int) = 0.0385], Reflections collected 3481, Refinement method, full-matrix least-squares on F ², Goodness-of-fit on F ² 0.902, Final R indices [I > 2σ(I)] R1 = 0.0827, wR2 = 0.0975, R indices (all data) R1 = 0.0393, wR2 = 0.0879, Extinction coefficient 0.0098 (7), Largest diff. peak and hole 0.169 and -0.161 eÅ^-3.

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