Issue 43, 2021
From the journal:

Chemical Science

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

Andrew J. Greener, ORCID logo ‡a   Patrycja Ubysz,‡a   Will Owens-Ward,a   George Smith,a   Ivan Ocaña,a   Adrian C. Whitwood, ORCID logo a   Victor Chechika  and  Michael J. James ORCID logo *a  

* Corresponding authors

a Department of Chemistry, University of York, Heslington, York, UK
E-mail: michael.james@york.ac.uk

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.

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

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Article information

DOI
https://doi.org/10.1039/D1SC04748E
Article type
Edge Article
Submitted
27 Aug 2021
Accepted
20 Oct 2021
First published
22 Oct 2021
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2021,12, 14641-14646

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

A. J. Greener, P. Ubysz, W. Owens-Ward, G. Smith, I. Ocaña, A. C. Whitwood, V. Chechik and M. J. James, Chem. Sci., 2021, 12, 14641 DOI: 10.1039/D1SC04748E

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