Advances on the Synthesis of N—N Bonds

doi:10.6023/cjoc202111019

Abstract

Nitrogen-nitrogen bonds are widely found in drugs, nature products and organic materials. Design and synthesis of nitrogen-nitrogen motifs with high efficiency have always been an important issue in organic chemistry. The nitrogen sources such as amines, nitriles, nitroso, and azides or other N-functionalized reagents, are commonly exist in organic compounds. Direct N-N coupling of these nitrogen sources provides a more convergent synthesis strategy to produce different heterocycles and hydrazines containing the N-N motif. In this paper, the intermolecular and intramolecular formation of N—N bond in recent years is reviewed, and the difficulties and future development of this method are prospected.

Key words: N-N coupling, N-containing group, N-heterocycle, N—N bond

Cite this article

Weizhe Zhao, Jiali Xu, Fan Yang, Xianghua Zeng. Advances on the Synthesis of N—N Bonds[J]. Chinese Journal of Organic Chemistry, 2022, 42(5): 1336-1345.

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Fig. & Tab. 29

Figure 1. Molecules containing N—N bond

Figure 2. Methods for construction of N—N bond

Scheme 1. Dehydrogenative coupling of diarylamines

Scheme 2. Dehydrogenative coupling of carbazoles

Scheme 3. Dehydrogenative coupling of secondary amines

Scheme 4. Nitrene-mediated intermolecular N—N coupling

Scheme 5. Iodine or phospine-mediated intermolecular N—N coupling

Scheme 6. Copper-catalyzed synthesis of triazoles

Scheme 7. Copper or base-mediated synthesis of triazoles

Scheme 8. Copper-mediated synthesis of tetrasubstituted pyrazoles

Scheme 9. Ti-catalyzed synthesis of tetrasubstituted pyrazoles

Scheme 10. Cu-catalyzed synthesis of pyrazolo[1,5-a]indole derivatives

Scheme 11. Pd-catalyzed synthesis of pyrido[1,2-b]indazoles

Scheme 12. Methods for the synthesis of 1H-indazoles

Scheme 13. Base-mediated synthesis of 2H-indazoles

Scheme 14. Synthesis of tetrazine derivatives

Scheme 15. Photocatalytic synthesis of diaziridines

Scheme 16. Catalyst-free synthesis of 1,2,3-triazoles

Scheme 17. Methods for synthesis of indazolone derivatives

Scheme 18. Methods for synthesis of 2H-indazoles

Scheme 19. Methods for synthesis of pyrido[1,2-b]indazoles

Scheme 20. Cu-catalyzed synthesis of 1H-indazoles

Scheme 21. Na2WO4-catalyzed synthesis of 1H-indazoles

Scheme 22. Methods for synthesis of 1H-pyrazoles

Scheme 23. Methods for synthesis of pyrazolin-5-ones

Scheme 24. Methods for synthesis of pyrazolines

Scheme 25. Methods for synthesis of triazolopyridines

Scheme 26. Methods for synthesis of cinnolines and phthalazin-1,4-diones

Scheme 27. Methods for synthesis of pyridazines

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N—N键合成方法的研究进展