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Nonheme iron complex-catalyzed efficient alcohol oxidation by t-BuOOH with N-hydroxyphthalimide (NHPI) as co-catalyst: Implication of high valent iron-oxo species
- Nonheme iron complex-catalyzed efficient alcohol oxidation by t-BuOOH with N-hydroxyphthalimide (NHPI) as co-catalyst: Implication of high valent iron-oxo species
- Bae, Jeong Mi; Lee, Myoung Mi; Lee, Seul Ah; Lee, Sun Young; Bok, Kwon Hee; Kim, Jinheung; Kim, Cheal
- Ewha Authors
- SCOPUS Author ID
- Issue Date
- Journal Title
- INORGANICA CHIMICA ACTA
- 0020-1693; 1873-3255
- vol. 451, pp. 8 - 15
- Nonheme iron complexes; Alcohol oxidation; High-valent iron-oxo species; tert-Butyl hydroperoxide; Imidazole; N-hydroxyphthalimide
- ELSEVIER SCIENCE SA
- SCI; SCIE; SCOPUS
- Two iron catalysts ([Fe(bpc)Cl-2][ELIN] (la) and [Fe(Me(2)bpb)Cl2][Et3NFI] (lb)) displayed efficient catalysis in oxidation of various alcohols to the corresponding carbonyl products using t-BuOOH as an oxidant in the presence of N-hydroxyphthalimide (NHPI) under mild conditions. la having an electron-withdrawing group showed a little better catalytic activity than that of lb with an electron-donating group. The mechanistic studies through Hammett plot, deuterium isotope effect, and the use of 2-methyl-1-phenylprop2-yl hydroperoxide (MPPH) as a mechanistic probe suggested that the reactive oxidants responsible for the alcohol oxidation possibly involved Fe-lv=0 species, alkoxy radical (Ra), and phthalimide N-oxyl radical (PINO center dot). On the other hand, the presence of imidazole increased the heterolytic cleavage of Fe-OOR intermediate to form Fe-v=0 species and accelerated its O-O bond cleavage rate. In particular, the formation of Fev=0 intermediate via the heterolytic cleavage of Fe-OOR species in the presence of imidazole in the catalytic oxidation systems of nonheme iron complexes with t-BuOOH was substantialized, for the first time, to the best of our knowledge. (C) 2016 Elsevier B.V. All rights reserved.
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