Denitrative Hydroxylation of Unactivated Nitroarenes**

Lee Duff; Harry Meakin; Adam Richardson; Andrew J. Greener; George W.A. Smith; Ivan Ocaña; Victor Chechik; Michael J. James

doi:10.1002/chem.202203807

Denitrative Hydroxylation of Unactivated Nitroarenes**

Lee Duff, Harry Meakin, Adam Richardson, Andrew J. Greener, George W.A. Smith, Ivan Ocaña, Victor Chechik, Michael J. James^*

^*Corresponding author for this work

Chemistry

Research output: Contribution to journal › Article › peer-review

Abstract

A one-step method for the conversion of nitroarenes into phenols under operationally simple, transition-metal-free conditions is described. This denitrative functionalization protocol provides a concise and economical alternative to conventional three-step synthetic sequences. Experimental and computational studies suggest that nitroarenes may be substituted by an electron-catalysed radical-nucleophilic substitution (S_RN1) chain mechanism.

Original language	English
Article number	e202203807
Number of pages	6
Journal	Chemistry - A European Journal
Early online date	8 Feb 2023
DOIs	https://doi.org/10.1002/chem.202203807
Publication status	E-pub ahead of print - 8 Feb 2023

Bibliographical note

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

Publisher Copyright:
© 2023 The Authors. Chemistry - A European Journal published by Wiley-VCH GmbH.

Keywords

denitrative functionalisation
hydroxylation
nitroarenes
radical anion
S1

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10.1002/chem.202203807Licence: CC BY

Chemistry A European J - 2023 - Duff - Denitrative Hydroxylation of Unactivated Nitroarenes
© 2023 The Authors.
Final published version, 2.68 MBLicence: CC BY

Cite this

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abstract = "A one-step method for the conversion of nitroarenes into phenols under operationally simple, transition-metal-free conditions is described. This denitrative functionalization protocol provides a concise and economical alternative to conventional three-step synthetic sequences. Experimental and computational studies suggest that nitroarenes may be substituted by an electron-catalysed radical-nucleophilic substitution (SRN1) chain mechanism.",

keywords = "denitrative functionalisation, hydroxylation, nitroarenes, radical anion, S1",

author = "Lee Duff and Harry Meakin and Adam Richardson and Greener, {Andrew J.} and Smith, {George W.A.} and Ivan Oca{\~n}a and Victor Chechik and James, {Michael J.}",

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AU - Duff, Lee

AU - Meakin, Harry

AU - Richardson, Adam

AU - Greener, Andrew J.

AU - Smith, George W.A.

AU - Ocaña, Ivan

AU - Chechik, Victor

AU - James, Michael J.

N1 - Funding Information: The authors would like to thank the University of York, the University of Manchester, the Leverhulme Trust (for an Early Career Fellowship, ECF‐2019‐135, M.J.J.) and the Royal Society (Research Grant RGS\R1\201268) for financial support. We would also like to thank Dr Jason Lynam, Dr William Unsworth and Prof. Peter O'Brien for helpful discussions. Publisher Copyright: © 2023 The Authors. Chemistry - A European Journal published by Wiley-VCH GmbH.

PY - 2023/2/8

Y1 - 2023/2/8

N2 - A one-step method for the conversion of nitroarenes into phenols under operationally simple, transition-metal-free conditions is described. This denitrative functionalization protocol provides a concise and economical alternative to conventional three-step synthetic sequences. Experimental and computational studies suggest that nitroarenes may be substituted by an electron-catalysed radical-nucleophilic substitution (SRN1) chain mechanism.

AB - A one-step method for the conversion of nitroarenes into phenols under operationally simple, transition-metal-free conditions is described. This denitrative functionalization protocol provides a concise and economical alternative to conventional three-step synthetic sequences. Experimental and computational studies suggest that nitroarenes may be substituted by an electron-catalysed radical-nucleophilic substitution (SRN1) chain mechanism.

KW - denitrative functionalisation

KW - hydroxylation

KW - nitroarenes

KW - radical anion

KW - S1

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DO - 10.1002/chem.202203807

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JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

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Denitrative Hydroxylation of Unactivated Nitroarenes**

Abstract

Bibliographical note

Keywords

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