Journal
CATALYSIS COMMUNICATIONS
Volume 10, Issue 15, Pages 1990-1994Publisher
ELSEVIER
DOI: 10.1016/j.catcom.2009.07.015
Keywords
Mukaiyama aldol reaction; Heterogeneous catalysis; Mesoporous materials; Aluminosilicates; Al-MCM-41
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Funding
- New Energy and Industrial Technology Development Organization (NEDO), Japan
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Mesoporous aluminosilicates, Al-MCM-41 (Si/Al = 20 and 50), efficiently catalyzed Mukaiyama aldol reaction of benzaldehyde with 1-(trimethylsiloxy)cyclohexene in CH2Cl2 at 0 degrees C to afford the corresponding beta-trimethylsiloxy ketone in quantitative yield. On the other hand, mesoporous silica (MCM-41), amorphous SiO2-Al2O3, and H-Y and H-ZSM-5 zeolites barely catalyzed the reaction. Additionally, the less ordered Al-MCM-41 prepared by mechanical compression exhibited much lower catalytic activity compared with Al-MCM-41, indicating that the presence of the ordered mesoporous structure in aluminosilicates is crucial for the catalysis. The Al-MCM-41 catalyzed Mukaiyama aldol reaction was applicable to a wide range of aldehydes and silyl enol ethers. Furthermore, the Al-MCM-41 catalyst could be recycled at least three times without any loss in the yield. Thus, mesoporous aluminosilicates are promising heterogeneous catalysts for fine chemicals synthesis. (C) 2009 Elsevier B.V. All rights reserved.
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