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DOI: 10.1055/s-0029-1219894
N-Alkylimidazole-Decorated Dendritic Catalysts for Baylis-Hillman Reaction
Contributor(s):Yasuhiro Uozumi, Yoichi M. A. Yamada, Chung Keun JinTel Aviv University, Israel
Supported N-Alkylimidazole-Decorated Dendrons as Heterogeneous Catalysts for the Baylis-Hillman Reaction
Chem. Commun. 2010, 46: 1965-1967
Publication History
Publication Date:
20 May 2010 (online)
Key words
Baylis-Hillman reaction - N-alkylated imidzoles - dendrons - heterogeneous catalysis
Significance
Polymer-supported dendritic catalysts [Gn(E-Im), Gn(A-Im), Gn(T-Im)] were prepared from Wang resins and N-alkylated imidazoles (1-3), and applied to the Baylis-Hillman reaction. Thus, the Baylis-Hillman reaction of methyl vinyl ketone and 4-nitrobenzaldehyde was performed with the catalytic resin G2(A-Im) (0.1 mmol of N-alkylated imidazole units) in DMF-H2O (9:1, v/v) at room temperature for 4 h to afford adduct 4 in 91% yield.
Comment
The addition of water improved the catalytic activity in the Baylis-Hillman reaction. The second-generation catalysts [G2(E-Im), G2(T-Im), G2(A-Im)] exhibited higher catalytic activity than their non-dendritic counterparts [G0(E-Im), G0(T-Im), G0(A-Im)].