Recent Progress on Light-Mediated C—N Bond-Forming Processes from Ammonia and Equivalents

doi:10.6023/cjoc202405038

Abstract

N-Containing organic compounds are widespread in natural products, drug molecules and organic materials. Therefore, it is of great importance to develop environmentally benign and efficient methods for constructing C—N bonds from simple and easily-available starting materials. Light is a widespread natural resource that is abundant, economical, and renewable. In addition, ammonia and its equivalents, as direct products of nitrogen fixation, are extremely economical and stable nitrogen-containing inorganic compounds, which serve as ideal sources of nitrogen. The efficient transfer of nitrogen atom from ammonia and its equivalents to diverse organic compounds represents the transfer of nitrogen from inorganic compounds to organic compounds resulting from the fixation of nitrogen gas. Therefore, it is of great value to develop the C—N bonding reaction involving ammonia and its equivalents by photocatalysis. The progress of light-catalyzed carbon-nitrogen bond-forming reactions involving ammonia and its equivalents over recent years is summarized. Moreover, a prospective on the further development of ammonia and inorganic ammonium salts for C—N bond-formation by photocatalysis is discussed.

Key words: photocatalysis, C—N bond-forming reaction, ammonia, ammonium salt, radical reaction

Cite this article

Shunxi Li, Lixu You, Yulong Li, Wei Shu. Recent Progress on Light-Mediated C—N Bond-Forming Processes from Ammonia and Equivalents[J]. Chinese Journal of Organic Chemistry, 2025, 45(5): 1460-1477.

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Fig. & Tab. 35

Scheme 1. Light-mediated C—N bond-forming reactions from ammonia its equivalents

Scheme 2. UV-light-catalyzed hydroamination of arylpropanes and styrenes for primary amines

Scheme 3. Photocatalytic metal-free synthesis of nitriles

Scheme 4. Metal-free and one-pot protocol for the synthesis of aryl nitrile from methylarenes

Scheme 5. N-Methylation of ammonia catalyzed by UV-visible light

Scheme 6. Visible-light-catalyzed 1,2-cyanodifluoromethylation of olefins

Scheme 7. Photocatalyzed oxidative condensation of benzyl alcohols with ammonia to nitrile

Scheme 8. Photocatalytic synthesis of HMT from methanol and ammonia

Scheme 9. Visible-light-catalyzed direct amination of allylic C—H bonds

Scheme 10. UV-light-catalyzed hydroamination of electron-rich styrenes and ammonia to access primary amines

Scheme 11. UV-light-catalyzed regioselective hydroamination of 2-vinylnaphthene with ammonia

Scheme 12. Visible-light-catalyzed synthesis of unprotected primary amines from carbonyls and ammonia

Scheme 13. Photocatalytic anti-Markovnikov hydroamination of olefins

Scheme 14. Visible-light-catalyzed hydroamination of N-acylenamines with ammonia

Scheme 15. Visible-light-catalyzed hydroamination of olefins with ammonium salts to aliphatic primary amines

Scheme 16. Organic photocatalyzed one-step synthesis of 2-piperidones by [1＋2＋3] strategy

Scheme 17. Visible-light-catalyzed regioselective hydroamination of 1,3-dienes with ammonia

Scheme 18. Pt/TiO2-catalyzed synthesis of primary aryl amines under UV light

Scheme 19. Visible-light-catalyzed C—H amination of (hetero)arenes with ammonium salts

Scheme 20. Visible-light-catalyzed conversion of furans to lactams

Scheme 21. Visible-light-catalyzed C—H amination of arenes with ammonia by releasing H2

Scheme 22. UV light-catalyzed Ullmann-Goldberg coupling to aryl primary amines

Scheme 23. UV light-catalyzed synthesis of α-ketoamide

Scheme 24. Visible-light-catalyzed C—H amination of electron- rich arenes with ammonium salts

Scheme 25. Visible-light and cobalt-catalyzed dehydrogenative aromatization of cyclohexanones with ammonia to anilines

Scheme 26. Visible light catalyzed substitution of aromatic carbon-fluorine bonds with inorganic ammonium salts for the synthesis of primary anilines

Scheme 27. Visible-light-catalyzed C—N coupling of aryl chloride with ammonia

Scheme 28. Visible-light and Co-catalyzed amidation of aryl carboxylic acids and ammonia

Scheme 29. Ti-V-MCM-41-catalyzed C—H amination of benzene with ammonia under UV light

Scheme 30. Visible-light and Ni-catalyzed C—N cross-coupling of aryl halides with ammonium salt

Scheme 31. Photo- and Ni-catalyzed synthesis of primary aryl amines using Werner salts as both nickel and nitrogen

Scheme 32. Visible-light-catalyzed exhaustive defluorinative coupling of vinyl trifluorides with ammonium salts for the synthesis of amides

Scheme 33. Visible-light-catalyzed synthesis of phenanthrdines from biaryl aldehydes with ammonium salts

Scheme 34. Photo- and Co-catalyzed synthesis of amides from alkenes, carbon monoxide and ammonia

Scheme 35. Visible-light and iodine-catalyzed oxidative synthesis of amides from terminal alkynes with ammonia

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