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Synfacts 2013; 9(4): 0451
DOI: 10.1055/s-0032-1318422
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart · New York

Dendritic Fluoroalcohols Catalyzed Alkene Epoxidation with H2O2

Contributor(s):
Yasuhiro Uozumi
,
Yoichi M. A. Yamada
,
Aya Ohno
Berkessel A, * Krämer J, Mummy F, Neudörfl J.-M, Haag R. University of Cologne and Freie Universität Berlin, Germany
Dendritic Fluoroalcohols as Catalysts for Alkene Epoxidation with Hydrogen Peroxide.

Angew. Chem. Int. Ed. 2013;
52: 739-743
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Further Information

Publication History

Publication Date:
15 March 2013 (online)

 
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Key words

alkenes - epoxidation - dendritic fluoroalcohols - hydrogen peroxide

Significance

Hyperbranched polyglycerol immobilized flluoroalcohols (catalyst A and B) were prepared and applied to the epoxidation of alkenes. Thus, the reaction of alkenes 1 and aqueous hydrogen peroxide with 20 mol% of the fluoroalcohol unit of the catalyst gave the corresponding epoxides 2 in up to quantitative yield.


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Comment

Catalysts A and B were recovered by ultrafiltration (molecular-weight cut-off of the membrane: 5 kDa) and reused twice for the epoxidation of cyclooctene without significant loss of catalytic activity. Hexafluoro-2-propanol showed lower catalytic activity for the epoxidation of 1d under similar conditions (24 h, 2d: 14% yield).


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