Issue 5, 2011

Iron-catalyzed epoxidation of olefins using hydrogen peroxide

Abstract

A practical method of olefin epoxidation was developed by combining FeCl3·6H2O and 1-methylimidazole in acetone using H2O2 as the terminal oxidant. This system showed very good reactivity toward epoxidation of both terminal and substituted alkenes. The use of tridentate and tetradentate amine-bis(phenolate) ligands as additives was also examined. Modest improvement in selectivity was achieved if a bulky tridentate ligand was used. Generally, however, the simple catalyst system involving ferric chloride, 1-methylimidazole and dilute H2O2 in acetone proved most successful in achieving good to excellent yields of epoxide products for a number of substrates, including aromatic and aliphatic alkenes.

Graphical abstract: Iron-catalyzed epoxidation of olefins using hydrogen peroxide

Supplementary files

Article information

Article type
Paper
Submitted
22 Dec 2010
Accepted
22 Feb 2011
First published
29 Mar 2011

Green Chem., 2011,13, 1230-1237

Iron-catalyzed epoxidation of olefins using hydrogen peroxide

K. Hasan, N. Brown and C. M. Kozak, Green Chem., 2011, 13, 1230 DOI: 10.1039/C0GC00943A

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