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Synfacts 2013; 9(1): 0117
DOI: 10.1055/s-0032-1317907
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart · New York

Aerobic Oxidation of Alcohols with Ru@PMO-IL

Contributor(s):
Yasuhiro Uozumi
,
Go Hamasaka
Karimi B, * Elhamifar D, Yari O, Khorasani M, Vali H, Clark JH, Hunt AJ. Institute for Advanced Studies in Basic Sciences, Zanjan and Yasouj University, Iran; McGill University, Montreal, Canada; University of York, UK
Synthesis and Characterization of Alkyl-Imidazolium-Based Periodic Mesoporous Organosilicas: A Versatile Host for the Immobilization of Perruthenate (RuO4 –) in the Aerobic Oxidation of Alcohols.

Chem. Eur. J. 2012;
18: 13520-13530
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Publication History

Publication Date:
17 December 2012 (online)

 
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Key words

oxidation - alcohols - carbonyl compounds - ruthenium - organosilica - catalysis

Significance

Perruthenate was supported on ionic-liquid-based periodic mesoporous organosilica (Ru@PMO-IL) via the reaction of 1,3-bis-(3-trimethoxysilylpropyl)imidazolium chloride with tetramethoxysilane, followed by treatment with KRuO4 (eq. 1). Ru@PMO-IL catalyzed the oxidation of alcohols in trifluorotoluene at 70–85 °C ­under 1 atm of oxygen to give the corresponding carbonyl compounds in up to >99% yield (24 examples, eq. 2).


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Comment

The catalyst was recovered by centrifugation and subjected to recycling runs. ICP-AES analysis showed no significant ruthenium leaching (<1 ppm) under the reaction conditions. Nitrogen adsorption and TEM analyses of the recovered catalyst revealed no morphology change of the mesoporous structure. However, a slight loss of catalytic activity was observed during the recycling runs (for the oxidation of benzyl alcohol; 2nd reuse: 99%, 4th reuse: 89%, 5th reuse: 75%).


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