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

Chemistry. 2023 Mar 16;29(16):e202203807. doi: 10.1002/chem.202203807. Epub 2023 Feb 8.

Authors

Lee Duff¹, Harry Meakin¹, Adam Richardson¹, Andrew J Greener¹, George W A Smith¹, Ivan Ocaña¹, Victor Chechik¹, Michael J James²

Affiliations

¹ Department of Chemistry, University of York Heslington, York, YO10 5DD, UK.
² Department of Chemistry, The University of Manchester, Oxford Road, Manchester, M13 9PL, UK.

PMID: 36594445
DOI: 10.1002/chem.202203807

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_RN 1) chain mechanism.

Keywords: SRN1; denitrative functionalisation; hydroxylation; nitroarenes; radical anion.

Abstract

Grants and funding