Visible-Light Promoted Photochemical Transformations of Azo Compounds

doi:10.6023/cjoc202405022

Abstract

Azo compounds are an essential part of organic synthesis due to their unique structures and properties. They serve not only as oxidants but also as coupling partners in heterocycle synthesis. In recent years, visible-light promoted reactions have garnered increasing attention from chemists because of their convenient operation and mild reaction conditions. Nowadays, visible-light promoted chemical transformations involving azo compounds have become one of the hotspots in the field of organic synthesis, and the related research reports are emerging in endlessly. For instance, azo compounds can be used to synthesize hydrazides and heterocycles. A comprehensive review of recent advancements in visible-light promoted photochemical transformations involving azo compound is provided, while the associated challenges and potential opportunities in this field are also discussed.

Key words: azo compound, visible-light, heterocycle synthesis

Cite this article

Shuchao Ma, Zele Chen, Jun Xuan. Visible-Light Promoted Photochemical Transformations of Azo Compounds[J]. Chinese Journal of Organic Chemistry, 2025, 45(5): 1669-1683.

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Fig. & Tab. 30

Scheme 1. CdS-promoted selective reductive hydrogenation of azobenzene

Scheme 2. Eosin Y-catalyzed reductive hydrogenation of azobenzene

Scheme 3. Reduction of azobenzenes by visible light combined with B2Pin2

Scheme 4. Metal- and catalyst-free reductive hydrogenation of azobenzenes

Scheme 5. Hydroacylation of dialkyl azodicarboxylates catalyzed by benzoylformic acid

Scheme 6. Graphite flakes-mediated hydroacylation of DIAD

Scheme 7. TBADT-catalyzed hydroacylation of DBAD

Scheme 8. Hydroacylation of dialkyl azodicarboxylates with acylsilanes

Scheme 9. Ucpt-catalyzed hydroacylation of dialkyl azodicarboxylates

Scheme 10. Decarboxylative hydroacylation of azobenzenes with α-keto acids

Scheme 11. PPh3-mediated hydroacylation of azobenzenes

Scheme 12. Hydrogenation of azo compounds with 4-acyl-sub- stituted Hantzsch esters

Scheme 13. Hydroalkylation of dialkyl azodicarboxylates catalyzed by CeCl3

Scheme 14. Hydroalkylation of DBAD by LMCT

Scheme 15. Hydroalkylation of DBAD using benzocyclic amines as α-aminoalkyl radical precursors

Scheme 16. Hydroalkylation of dialkyl azodicarboxylates using N-substituted indole-2-carboxylic acid as α-aminoalkyl radical precursors

Scheme 17. Hydroalkylation of dialkyl azodicarboxylates using tetrahydropyrrole derivatives as α-aminoalkyl radical precursors

Scheme 18. Generation of α-aminoalkyl radicals by construction of EDA complexes

Scheme 19. Hydroalkylation of dialkyl azodicarboxylates using glycine derivatives as α-aminoalkyl radical precursors

Scheme 20. Hydroalkylation of dialkyl azodicarboxylates with quinoxalinone and benzoxazinone derivatives

Scheme 21. Simple synthesis of rac-GW420867X

Scheme 22. Decarboxylative addition cyclization of azobenzenes with glycine derivatives

Scheme 23. 1,3-Dipolar cycloaddition of azobenzenes with azomethine ylides

Scheme 24. [3＋2] cycloaddition of azobenzenes with benzynes

Scheme 25. Synthesis of 2H-indazole derivatives achieved in metal-free and catalyst-free conditions

Scheme 26. Three-component reactions of dialkyl azodicarboxylates, diazoalkanes and nitriles

Scheme 27. C—H acylation of azobenzenes with α-keto acids

Scheme 28. Diboronation of azobenzenes with tetraaryl diborane

Scheme 29. Hydrophosphorylation of azobenzenes with diarylphosphine oxides

Scheme 30. Difunctionalization of dialkyl azodicarboxylates

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可见光促进偶氮化合物参与的光化学转化