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

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.

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Item Type:	Article
Authors/Creators:	Greener, Andrew J. Ubysz, Patrycja Owens-Ward, Will Smith, George Ocaña, Ivan Whitwood, Adrian C. Chechik, Victor https://orcid.org/0000-0002-5829-0122 James, Michael J. https://orcid.org/0000-0003-2591-0046
Copyright, Publisher and Additional Information:	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.
Dates:	Accepted: 20 October 2021 Published: 22 October 2021
Institution:	The University of York
Academic Units:	The University of York > Faculty of Sciences (York) > Chemistry (York)
Depositing User:	Pure (York)
Date Deposited:	19 Nov 2021 13:20
Last Modified:	10 Apr 2025 23:30
Published Version:	https://doi.org/10.1039/d1sc04748e
Status:	Published
Refereed:	Yes
Identification Number:	10.1039/d1sc04748e
Related URLs:	http://www.scopus.com/inward/record.url?...
Open Archives Initiative ID (OAI ID):	oai:eprints.whiterose.ac.uk:180658

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

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