Dendritic Fluoroalcohols as Catalysts for Alkene Epoxidation with Hydrogen Peroxide

Cooperativity is the key for mild catalytic epoxidation: The immobilization of fluoroalcohols on dendritic polyglycerol (by “click chemistry”) provides organocatalysts that can form multiple hydrogen bonds. The epoxidation of alkenes with aqueous hydrogen peroxide proceeds efficiently in the presenc...

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Published inAngewandte Chemie (International ed.) Vol. 52; no. 2; pp. 739 - 743
Main Authors Berkessel, Albrecht, Krämer, Jan, Mummy, Florian, Neudörfl, Jörg-M., Haag, Rainer
Format Journal Article
LanguageEnglish
Published Weinheim WILEY-VCH Verlag 07.01.2013
WILEY‐VCH Verlag
Wiley
Wiley Subscription Services, Inc
EditionInternational ed. in English
Subjects
alcohols
Catalysis
Catalysts
Chemistry
Chemistry, Multidisciplinary
Epoxidation
Filtration
Hydrogen bonds
Hydrogen peroxide
hyperbranched polymer
Olefins
organocatalysis
Physical Sciences
polyglycerol
Polyglycerols
Science & Technology
SELECTIVE OXIDATION
ACTIVATION
OLEFIN EPOXIDATION
REAGENTS
polyglycerol
alcohols
organocatalysis
epoxidation
SOLVENTS
SALEN
FLUORINATED ALCOHOLS
hyperbranched polymer
EFFICIENT
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Summary:Cooperativity is the key for mild catalytic epoxidation: The immobilization of fluoroalcohols on dendritic polyglycerol (by “click chemistry”) provides organocatalysts that can form multiple hydrogen bonds. The epoxidation of alkenes with aqueous hydrogen peroxide proceeds efficiently in the presence of dendritic fluoroalcohol catalysts. The supported catalysts can be separated by membrane filtration and reused.
Bibliography:Financial support by the Fonds der Chemischen Industrie is gratefully acknowledged. J.K. thanks Henkel KGaA, Düsseldorf, for a doctoral fellowship. A.B. acknowledges COST Membership (CM0905, Organocatalysis). R.H. would like to acknowledge the financial support from the Cluster of Excellence "Unifying Concepts in Catalysis".
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ArticleID:ANIE201206003
Fonds der Chemischen Industrie
ark:/67375/WNG-WM90J8BD-B
These authors contributed equally to this work.
Financial support by the Fonds der Chemischen Industrie is gratefully acknowledged. J.K. thanks Henkel KGaA, Düsseldorf, for a doctoral fellowship. A.B. acknowledges COST Membership (CM0905, Organocatalysis). R.H. would like to acknowledge the financial support from the Cluster of Excellence “Unifying Concepts in Catalysis”.
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ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201206003