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Trapping of a Highly Reactive Oxoiron(IV) Complex in the Catalytic Epoxidation of Olefins by Hydrogen Peroxide
- Trapping of a Highly Reactive Oxoiron(IV) Complex in the Catalytic Epoxidation of Olefins by Hydrogen Peroxide
- Engelmann, Xenia; Malik, Deesha D.; Corona, Teresa; Warm, Katrin; Farquhar, Erik R.; Swart, Marcel; Nam, Wonwoo; Ray, Kallol
- Ewha Authors
- SCOPUS Author ID
- Issue Date
- Journal Title
- ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
- ANGEWANDTE CHEMIE-INTERNATIONAL EDITION vol. 58, no. 12, pp. 4012 - 4016
- bioinorganic chemistry; catalysis; nonheme oxoiron intermediates; regioselectivity; stereoselective epoxidation
- WILEY-V C H VERLAG GMBH
- SCIE; SCOPUS
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- The generation of a nonheme oxoiron(IV) intermediate, [(cyclam)Fe-IV(O) (CH3CN)](2+) (2; cyclam=1,4,8,11-tetraazacyclotetradecane), is reported in the reactions of [(cyclam)Fe-II](2+) with aqueous hydrogen peroxide (H2O2) or a soluble iodosylbenzene (sPhIO) as a rare example of an oxoiron(IV) species that shows a preference for epoxidation over allylic oxidation in the oxidation of cyclohexene. Complex 2 is kinetically and catalytically competent to perform the epoxidation of olefins with high stereo- and regioselectivity. More importantly, 2 is likely to be the reactive intermediate involved in the catalytic epoxidation of olefins by [(cyclam)-Fe-II](2+) and H2O2. In spite of the predominance of the oxoiron(IV) cores in biology, the present study is a rare example of high-yield isolation and spectroscopic characterization of a catalytically relevant oxoiron(IV) intermediate in chemical oxidation reactions.
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