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Lim, Mi Hee
MetalloNeuroChemistry Lab (MNCL)
Research Interests
  • Neurodegenerative disease, small molecule design, network between metal, proteins, and ROS

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Parallel mechanistic studies on the counterion effect of manganese salen and porphyrin complexes on olefin epoxidation by iodosylarenes

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Title
Parallel mechanistic studies on the counterion effect of manganese salen and porphyrin complexes on olefin epoxidation by iodosylarenes
Author
Park, SESong, WJRyu, YOLim, Mi HeeSong, RKim, KMNam, W
Keywords
Biomimetic oxidation; Epoxidation; Iodosylarene; Manganese porphyrin; Salen
Issue Date
2005-02
Publisher
ELSEVIER SCIENCE INC
Citation
JOURNAL OF INORGANIC BIOCHEMISTRY, v.99, no.2, pp.424 - 431
Abstract
Counterions of manganese(III) porphyrin complexes influence diastereoselectivity in cis-stilbene epoxidation and product distribution in cyclohexene epoxidation markedly. In the epoxidation of cis-stilbene by iodosylbenzene carried out in a solvent mixture of CH 3CN and CH 2Cl 2, trans-stilbene oxide is the major product in the reaction of manganese complexes bearing a ligating anion (i.e., Cl -), whereas cis-stilbene oxide is the dominant product in the reactions of manganese complexes bearing a poorly-ligating anion (i.e., CF 3SO 4 -). In cyclohexene epoxidation, the yields of allylic oxidation products such as cyclohexenol and cyclohexenone are higher when the counterion of the manganese catalysts is Cl - than when the counterion is CF 3SO 4 -. The product selectivities are also dependent on the nature of iodosylarenes and the axial and porphyrin ligands of the manganese porphyrin catalysts. The observation that product selectivities are different depending on the iodosylarenes may indicate the involvement of multiple oxidants in oxygen atom transfer reactions. These results are compared with those observed in manganese salen-catalyzed epoxidation of olefins by iodosylarenes.
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DOI
10.1016/j.jinorgbio.2004.10.015
ISSN
0162-0134
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PHY_Journal Papers
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