Issue 67, 2024

Shining light on the nitro group: distinct reactivity and selectivity

Abstract

The nitro moiety is an indispensable functional group in organic synthesis due to its facile introduction and reduction to the corresponding amines for a plethora of organic transformations. Owing to its distinct electronegative and conventional properties, it has been used for activated aromatic nucleophilic substitution (SNAr) reactions, Smiles reactions, Henry reactions, acyl anion equivalents, etc. Recently, the excellent photochemical properties of nitroarenes have been rediscovered by several groups, and their untapped potential in organic synthesis under UV or visible light irradiation has been exploited. Photoexcited nitroarenes can undergo facile reduction to amines, azo-coupling, metal-free reductive C–N coupling with boronic acids via a 1,2-boronate shift, hydrogen atom transfer (HAT), oxygen atom transfer for anaerobic oxidation of organic molecules, molecular editing via nitrene intermediates, denitrative coupling of β-nitrostyrene, radical α-alkylation of nitroalkanes, etc. They have also been used as a photolabile protecting group in medicinal chemistry and chemical biology applications. Here, we summarise the recent findings on visible-light-mediated transformations involving nitro-containing organic molecules.

Graphical abstract: Shining light on the nitro group: distinct reactivity and selectivity

Article information

Article type
Highlight
Submitted
28 Cax 2024
Accepted
18 Qad 2024
First published
18 Qad 2024

Chem. Commun., 2024,60, 8806-8823

Shining light on the nitro group: distinct reactivity and selectivity

R. Jana and K. Pradhan, Chem. Commun., 2024, 60, 8806 DOI: 10.1039/D4CC02582B

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