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N-Hydroxyphthalimide: A Hydrogen Atom Transfer Mediator in Hydrocarbon Oxidations Promoted by Nonheme Iron(IV)-Oxo
Alessia Barbieri1, Osvaldo Lanzalunga1, Andrea Lapi1
1Dipartimento di Chimica , Università di Roma "La Sapienza", Istituto CNR per i Sistemi Biologici (ISB-CNR), Sezione Meccanismi di Reazione , P.le A. Moro , 5 I-00185 Rome , Italy.
The Journal of Organic Chemistry
|September 19, 2019
Abstract:
The oxidation of a series of hydrocarbons by the nonheme iron(IV)-oxo complex [(N4Py)FeIV═O]2+ is efficiently mediated by N-hydroxyphthalimide. The increase of reactivity is associated to the oxidation of the mediator to the phthalimide N-oxyl radical, which efficiently abstracts a hydrogen atom from the substrates, regenerating the mediator in its reduced form.