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Radical–anion coupling through reagent design: hydroxylation of aryl halides

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JournalChemical Science
DateAccepted/In press - 20 Oct 2021
DatePublished (current) - 22 Oct 2021
Issue number43
Volume12
Number of pages6
Pages (from-to)14641-14646
Original languageEnglish

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.

Bibliographical note

Funding Information:
The authors would like to thank the Wild Fund, the University of York, the Leverhulme Trust (for an Early Career Fellowship, ECF-2019-135, M. J. J.) and the Royal Society (Research Grant RGS\R1\201268) for nancial support. We would also like to thank Prof. Peter O'Brien and Dr William P. Unsworth for helpful discussions.

Publisher Copyright:
© The Royal Society of Chemistry 2021.

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