Radical–Anion Coupling Through Reagent Design: Hydroxylation of Aryl Halides

12 August 2021, Version 1
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

The design and development of an oxime-based hydroxylation reagent, which can chemoselectively convert aryl halides (X = F, Cl, Br, I) into phenols under operationally simple, transition-metal-free conditions is described. Key to the success of this approach was the identification of a reducing oxime anion which can interact and couple with open-shell aryl radicals. Experimental and computational studies support the proposed radical-nucleophilic substitution chain mechanism.

Keywords

Hydroxylation
SRN1
Transition-Metal-Free
Coupling
Radical-Anion

Supplementary materials

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Description
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Supporting Information
Description
Experimental procedures, characterisation data, computational details, and copies of 1H, 13C and 19F NMR spectra for all compounds featured in this manuscript.
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