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

Ming-Jin Fan; Gao-Qiang Li; Lian-Hua Li; Shang-Dong Yang; Yong-Min Liang

doi:10.1055/s-2006-942437

PAPER

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

Ming-Jin Fan^a, Gao-Qiang Li^a, Lian-Hua Li^a, Shang-Dong Yang^a, Yong-Min Liang*^a,b
^a State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, P. R. of China
^b Lanzhou Institute of Chemical Physics, Chinese Academy of Science, Lanzhou, 730000, P. R. of China
Fax: +86(931)8912582; e-Mail: liangym@lzu.edu.cn;

Abstract

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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.

Key words

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

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References

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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) Å³, 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.

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