Recent Progress on Radical-Mediated Activation of Nitroarenes

doi:10.6023/cjoc202502017

Abstract

Nitroarene is one of the cheapest and most readily available raw materials in the chemical industry and is often used as multifunctional building blocks. In the past, the synthesis of nitrogen-containing compounds mainly depended on aniline. However, the utilization of nitroarenes can save one or more steps as compared to anilines. Therefore, the construction of nitrogen-containing compounds using nitroarenes as potential amino sources has become one of the research hotspots in recent years. Due to the advantages of radicals, such as high activity, mild reaction conditions, and good functional group compatibility, good progress has been made on radical-mediated activation of nitroarenes in recent years, and a variety of reaction types have been implemented. In this review, the recent progress in radical-mediated activation of nitroarenes under different catalytic conditions is summarized. The reaction substrate compatibility, mechanism, applications, advantages, and limitations in this field are also discussed in detail.

Key words: nitroarenes, radical, activation reaction, nitrogen-containing compounds

Cite this article

Binbin Zhang, Lu'na Liu, Yangbin Zhu, Dong Zou. Recent Progress on Radical-Mediated Activation of Nitroarenes[J]. Chinese Journal of Organic Chemistry, 2025, 45(8): 2698-2725.

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Fig. & Tab. 39

Scheme 1. Fe-catalyzed hydroamination of olefins with nitro- arenes

Scheme 2. Fe-catalyzed reductive coupling of alkyl halides with nitroarenes

Scheme 3. Cu-catalyzed cross-coupling of nitroarenes with 4- alkyl-1,4-dihydropyridines

Scheme 4. Ni-catalyzed C—N coupling of aryl halides with nitroarenes

Scheme 5. Photoinduced reduction of nitroarenes and tandem C—N cross-coupling with haloarenes

Scheme 6. Fe-catalyzed decarboxylation C—N coupling of carboxylic acid with nitroarenes

Scheme 7. Fe-catalyzed decarboxylative amination with nitroarenes to construct secondary amines

Scheme 8. Visible light-assisted nickel-catalyzed amination of three components

Scheme 9. Dual nickel/photoredox-catalyzed synthesis of N-formyl N,N'-diaryl ethylenediamines

Scheme 10. Metallaphotocatalytic triple couplings for modular synthesis of elaborate N-trifluoroalkyl anilines

Scheme 11. Co-catalyzed chemoselective reduction of nitro- arenes

Scheme 12. Selective reduction of nitroarenes to aryl amines promoted by visible light

Scheme 13. Visible-light-mediated C—H amination of unactivated alkanes with nitroarenes

Scheme 14. Proposed mechanism of C—H amination of unactivated alkanes with nitroarenes

Scheme 15. Electroreductive carboxylic acids and nitroarenes coupling reaction

Scheme 16. Fe-catalyzed synthesis of amides from nitroarenes and benzaldehydes

Scheme 17. Photocatalytic synthesis of sulfinamides and sulfoxides from nitroarenes

Scheme 18. Transition metal-free synthesis of thioamides from nitroarenes

Scheme 19. Decarboxylative/oxidative amidation of aryl α-ketocarboxylic acids with nitroarenes

Scheme 20. Visible-light-induced intramolecular reductive cyclization of o-nitroarenes for the synthesis of quinazolinone derivatives

Scheme 21. Photo-driven reduction/cyclization of nitroarenes for the synthesis of quinazolinone derivatives

Scheme 22. Visible-light catalyzed [1＋2＋2] cycloaddition of nitroarenes

Scheme 23. Visible-light-induced α,γ-C(sp3)—H difunctionalization of piperidines

Scheme 24. Photo-induced redox cascade reaction of nitroarenes and amines

Scheme 25. Switchable redox annulation of 2-nitroarylethanols affording N-heterocycles

Scheme 26. Synthesis of polysubstituted azepanes by dearomative ring expansion of nitroarenes

Scheme 27. Synthesis of 2-arylbenzothiazol-5-amines from N,N-dialkyl-3-nitroanilines

Scheme 28. Transition-metal-free cycloadditions of nitroarenes and aldimines

Scheme 29. Enantioselective N-heterocyclic carbene-catalyzed β-hydroxylation of enals using nitroarenes

Scheme 30. NHC-catalyzed enantioselective transferring of oxygen atoms to enals

Scheme 31. Fe-catalyzed hydration of alkenes using nitroarenes

Scheme 32. Intramolecular radical oxygen-transfer reactions using nitroarenes

Scheme 33. Olefin dihydroxylation using nitroarenes as photoresponsive oxidants

Scheme 34. Anaerobic C—H hydroxylation of aliphatic systems promoted by photoexcited nitroarenes.

Scheme 35. Photoinduced oxygen transfer using nitroarenes for the anaerobic cleavage of alkenes

Scheme 36. Photoexcited nitroarenes for the oxidative cleavage of alkenes

Scheme 37. Transition-metal-free oxygen transfer using nitroarenes for the synthesis of N-benzoylbenzamidinates

Scheme 38. Cu-catalyzed oxygen transfer using nitroarenes for direct synthesis of 2-aminophenol derivatives

Scheme 39. A new method of photoinduced carbonylation modification of polymers

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