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Issue 77, 2015
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Mechanistic elucidation of C–H oxidation by electron rich non-heme iron(iv)–oxo at room temperature

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Abstract

Non-heme iron(IV)–oxo species form iron(III) intermediates during hydrogen atom abstraction (HAA) from the C–H bond. While synthesizing a room temperature stable, electron rich, non-heme iron(IV)–oxo compound, we obtained iron(III)–hydroxide, iron(III)–alkoxide and hydroxylated-substrate-bound iron(II) as the detectable intermediates. The present study revealed that a radical rebound pathway was operative for benzylic C–H oxidation of ethylbenzene and cumene. A dissociative pathway for cyclohexane oxidation was established based on UV-vis and radical trap experiments. Interestingly, experimental evidence including O-18 labeling and mechanistic study suggested an electron transfer mechanism to be operative during C–H oxidation of alcohols (e.g. benzyl alcohol and cyclobutanol). The present report, therefore, unveils non-heme iron(IV)–oxo promoted substrate-dependent C–H oxidation pathways which are of synthetic as well as biological significance.

Graphical abstract: Mechanistic elucidation of C–H oxidation by electron rich non-heme iron(iv)–oxo at room temperature

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Supplementary files

Article information


Submitted
10 Jun 2015
Accepted
03 Aug 2015
First published
04 Aug 2015

This article is Open Access

Chem. Commun., 2015,51, 14469-14472
Article type
Communication
Author version available

Mechanistic elucidation of C–H oxidation by electron rich non-heme iron(IV)–oxo at room temperature

S. Rana, A. Dey and D. Maiti, Chem. Commun., 2015, 51, 14469
DOI: 10.1039/C5CC04803F

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