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Synfacts 2010(6): 0723-0723  
DOI: 10.1055/s-0029-1219894
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart ˙ New York

N-Alkylimidazole-Decorated Dendritic Catalysts for Baylis-Hillman Reaction

Contributor(s):Yasuhiro Uozumi, Yoichi M. A. Yamada, Chung Keun Jin
K. Goren, M. Portnoy*
Tel Aviv University, Israel
Supported N-Alkylimidazole-Decorated Dendrons as Heterogeneous Catalysts for the Baylis-Hillman Reaction
Chem. Commun.  2010,  46:  1965-1967  
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Publication History

Publication Date:
20 May 2010 (online)

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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)].

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