Recent Advances in Functionalization of Aromatic C(sp2)—H Bonds Based on N-Nitroso Direction

doi:10.6023/cjoc202305029

Abstract

In recent years, examples of activation of aromatic C(sp²)—H bonds successfully constructing C—C bonds and C—heteroatom bonds through N-nitroso synergistic chelation with transition metals have been reported. It is based on the oxidative cleavage of internal N—N bonds, and does not require the addition of external oxidants during the reaction process. After the reaction completion, it can leave on its own, which has made it develop into a new and efficient directing group, and has received widespread attention from researchers. The latest research progress on functionalization of aromatic C(sp²)—H bonds based on N-nitroso direction is summarized.

Key words: C—H bond activation, directing group, N-nitroso, aromatic functionalization

Cite this article

Fang Wang, Lei Wang. Recent Advances in Functionalization of Aromatic C(sp²)—H Bonds Based on N-Nitroso Direction[J]. Chinese Journal of Organic Chemistry, 2023, 43(12): 4157-4167.

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Fig. & Tab. 33

Scheme 1. Rh(III)-catalyzed amino ortho-alkenylation of aromatic hydrocarbons

Scheme 2. Rh(III)-catalyzed reaction of N-nitroso aromatic amines with ethyl 2-oxoacetate

Scheme 3. Pd (II)-catalyzed amino ortho-acylation of aromatic hydrocarbons

Scheme 4. Pd(II)-catalyzed amino ortho-acylation of aromatic hydrocarbons

Scheme 5. Rh(III)-catalyzed amino ortho-α-fluoroalkylation of aromatic hydrocarbons

Scheme 6. Rh(III)-catalyzed amino ortho-alkenylation of aromatic hydrocarbons

Scheme 7. Rh (III)-catalyzed amino ortho-heteroarylation of aromatic hydrocarbons

Scheme 8. Rh(III)-catalyzed amino ortho-arylation of aromatic hydrocarbons

Scheme 9. Rh(III)-catalyzed ortho-amino-alkylation of aromatic hydrocarbons

Scheme 10. Rh(III)-catalyzed ortho-amino-alkylation of aromatic hydrocarbons

Scheme 11. Electrochemical oxidation of N-nitrosoaniline and α-oxycarboxylic acid

Scheme 12. Pd(II)-catalyzed amino ortho-alkoxylation of aromatic hydrocarbons

Scheme 13. Pd(II)-catalyzed amino ortho-alkoxylation of aromatic hydrocarbons

Scheme 14. Rh(III)-catalyzed amino direct ortho-amination of aromatic hydrocarbons

Scheme 15. Rh(III)-catalyzed amino direct ortho-amination of aromatic hydrocarbons

Scheme 16. Zn(II)-catalyzed amino ortho-nitration of aromatic hydrocarbons

Scheme 17. Rh(III)-catalyzed amino ortho-halogenation of aromatic hydrocarbons

Scheme 18. Rh(III)-catalyzed reaction of N-nitrosoaniline with alkynes

Scheme 19. Rh(III)-catalyzed reaction of N-nitrosoaniline with alkynes

Scheme 20. Rh(III)-catalyzed reaction of N-nitrosoaniline with diazo compounds

Scheme 21. Co(III)-catalyzed reaction of N-nitrosoaniline with alkynes

Scheme 22. Rh(III)-catalyzed synthesis of 1,2-disubstituted benzimidazoles

Scheme 23. Co(III)-catalyzed reaction of N-nitrosoaniline and α-diazo-β-ketone ester

Scheme 24. Rh(III)-catalyzed reaction of N-nitrosoaniline with alkynes

Scheme 25. Rh(III)-catalyzed reaction of N-nitrosoaniline with cyclopropenone

Scheme 26. Rh(III)-catalyzed reaction of N-nitrosoaniline and sulfonyl sulfoxide

Scheme 27. Rh(III)-catalyzed synthesis of 3-sulfonyl indoles

Scheme 28. Rh(II)-catalyzed amino ortho-acylation of aromatic hydrocarbons oxidative Heck and amidation reaction

Scheme 29. Synthesis of N-alkyl indoles from N-nitrosoanilines and iodonium ylides

Scheme 30. N-Nitrosoanilines with iodonium ylides for the synthesis of polysubstituted tetrahydroxycarbazol-4-ones

Scheme 31. Pd(II)-catalyzed synthesis of N-alkyl-2-amino- benzophenones

Scheme 32. Rh(III)-catalyzed amino ortho-cyanidation of aromatic hydrocarbon

Scheme 33. Co(III)-catalyzed N-alkylation of N-nitroso aromatic hydrocarbons

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基于N-亚硝基导向的芳烃C(sp²)—H键官能团化研究进展

Recent Advances in Functionalization of Aromatic C(sp²)—H Bonds Based on N-Nitroso Direction

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基于N-亚硝基导向的芳烃C(sp2)—H键官能团化研究进展