N-Hydroxyphthalimide: A Hydrogen Atom Transfer Mediator in Hydrocarbon Oxidations Promoted by Nonheme Iron(IV)-Oxo Complexes

J Org Chem. 2019 Nov 1;84(21):13549-13556. doi: 10.1021/acs.joc.9b01813. Epub 2019 Sep 27.

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.

Publication types

  • Research Support, Non-U.S. Gov't