Efficient catalysis of mesoporous Al-MCM-41 for Mukaiyama aldol reactions |
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Authors: | Katsuyuki Iwanami Toshiyasu Sakakura Hiroyuki Yasuda |
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Affiliation: | aNational Institute of Advanced Industrial Science and Technology (AIST), Tsukuba Central 5, 1-1-1 Higashi, Tsukuba, Ibaraki 305-8565, Japan |
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Abstract: | 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 °C to afford the corresponding β-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. |
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Keywords: | Mukaiyama aldol reaction Heterogeneous catalysis Mesoporous materials Aluminosilicates Al-MCM-41 |
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