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Oxidative N-dealkylation reactions by oxoiron(IV) complexes of nonheme and heme ligands

Title
Oxidative N-dealkylation reactions by oxoiron(IV) complexes of nonheme and heme ligands
Authors
Nehru K.Seo M.S.Kim J.Nam W.
Ewha Authors
남원우김진흥서미숙
SCOPUS Author ID
남원우scopus; 김진흥scopus
Issue Date
2007
Journal Title
Inorganic Chemistry
ISSN
0020-1669JCR Link
Citation
vol. 46, no. 1, pp. 293 - 298
Indexed
SCI; SCIE; SCOPUS WOS scopus
Abstract
Nonheme and heme iron monooxygenases participate in oxidative N-dealkylation reactions in nature, and high-valent oxoiron(IV) species have been invoked as active oxidants that effect the oxygenation of organic substrates. The present study describes the first example of the oxidative N-dealkylation of N,N-dialkylamines by synthetic nonheme oxoiron(IV) complexes and the reactivity comparisons of nonheme and heme oxoiron(IV) complexes. Detailed mechanistic studies were performed with various N,N-dialkylaniline substrates such as para-substituted N,N-dimethylanilines, para-chloro-N-ethyl-N- methylaniline, para-chloro-N-cyclopropyl-N-isopropylaniline, and deuteriated N,N-dimethylanilines. The results of a linear free-energy correlation, inter- and intramolecular kinetic isotope effects, and product analysis studied with the mechanistic probes demonstrate that the oxidative N-dealkylation reactions by nonheme and heme oxoiron(IV) complexes occur via an electron transfer-proton transfer (ET-PT) mechanism. © 2007 American Chemical Society.
DOI
10.1021/ic0614014
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자연과학대학 > 화학·나노과학전공 > Journal papers
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