Progress of N-Amino Pyridinium Salts as Nitrogen Radical Precursors in Visible Light Induced C—N Bond Formation Reactions

doi:10.6023/cjoc202207019

Abstract

Because of the redox properties of pyridine salt, it is found that N-amino pyridine salt plays an important role in free radical chemistry. N-Amino pyridinium salts easily undergo single electron reduction and N—N bond fragmentation to deliver N radicals. In this review, the advances of N-amino pyridinium salt serves as a powerful nitrogen radical precursor in visible light induced reactions for C—N bond formation are summarized in the last three years. According to the reaction substrates, the review is divided into three parts: react with arenes, react with olefins, and react with alkanes.

Key words: pyridinium salts, radical, visible light, green organic synthesis

Cite this article

Shaohui Yang, Jingcheng Song, Daoqing Dong, Hao Yang, Mengyu Zhou, Huishu Zhang, Zuli Wang. Progress of N-Amino Pyridinium Salts as Nitrogen Radical Precursors in Visible Light Induced C—N Bond Formation Reactions[J]. Chinese Journal of Organic Chemistry, 2022, 42(12): 4099-4110.

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Fig. & Tab. 31

Scheme 1. N-Amino pyridinium salts as nitrogen radical precursors

Scheme 2. Amidation of arenes and heteroarenes

Scheme 3. Suggested mechanism

Scheme 4. Visible-light mediated imidazo[1,2-a]pyridine C—H amination with N-aminopyridinium salt accelerated by surfactant in water

Scheme 5. Proposed reaction mechanism

Scheme 6. Scope of the photocatalytic aminohydroxylation

Scheme 7. Proposed reaction mechanism

Scheme 8. Regiospecific three-component aminofluorination of olefins via photoredox catalysis

Scheme 9. A proposed mechanism

Scheme 10. Alkene functionalization for the stereospecific synthesis of substituted aziridines by visible-light photoredox catalysis

Scheme 11. Proposed mechanism

Scheme 12. Amination of π?nucleophiles

Scheme 13. Plausible mechanism of the amination of π?nucleophiles

Scheme 14. Selective 1,2-aminoisothiocyanation of 1,3-dienes

Scheme 15. Proposed catalytic cycle

Scheme 16. Photoredox catalytic three-component amidoazidation of 1,3-dienes

Scheme 17. Proposed reaction mechanism

Scheme 18. N-Centered radical addition/semipinacol rearrangement for the convenient synthesis of β-amino (spiro)cyclic ketones

Scheme 19. Proposed reaction mechanism

Scheme 20. Amino-heteroarylation of unactivated olefins to access distal amino ketones

Scheme 21. Proposed mechanism

Scheme 22. 1,3-Aminopyridylation of [1.1.1]propellane with N-aminopyridinium salts

Scheme 23. Proposed reaction mechanism

Scheme 24. Amidation/cyclization of arylacrylamides using N-aminopyridinium salts

Scheme 25. Proposed mechanism of amidation/cyclization of arylacrylamides

Scheme 26. Synthesis of γ?lactams enabled by photoinduced deaminative [3+2] annulation reaction

Scheme 27. Proposed reaction mechanism

Scheme 28. Visible-light-driven [3+2]/[4+2] annulation reactions of alkenes with N?aminopyridinium salts

Scheme 29. Proposed reaction mechanism

Scheme 30. 1,3-Aminopyridylation of [1.1.1]propellane with N-aminopyridinium salts

Scheme 31. Proposed reaction mechanism

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