Recent Advances in Copper-Catalyzed N-O Cleavage Strategy

doi:10.6023/cjoc201904037

Abstract

N-O bond cleavage is one of the most efficient and powerful strategies to introduce N-or O-functional groups into molecules in organic synthesis. Copper catalyst, as the abundant in earth and inexpensive advantages has been widely used to construct C-N and C-O bond. Furthermore, N-O bond cleavage has been successfully applied in the total synthesis of natural products and pharmaceuticals. The new development of copper-catalyzed N-O bond cleavage and its application in the total synthesis of natural products and pharmaceuticals in recent years have been summarized.

Key words: copper-catalysis, heterocyclic compounds, N-O cleavage, cascade reaction, rearrangement reaction

Cite this article

Lei Lu, Li Chengjing, Mo Dongliang. Recent Advances in Copper-Catalyzed N-O Cleavage Strategy[J]. Chinese Journal of Organic Chemistry, 2019, 39(11): 2989-3012.

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Fig. & Tab. 37

Scheme 1. Type of N—O bond cleavage

Figure 1. Copper-catalyzed three component cascade reaction to prepare polysubstituted pyridines

Scheme 2. Proposed mechanism of copper-catalyzed three component cascade reaction

Scheme 3. Coupling reaction of copper-catalyzed oxime acetates oxidative

Scheme 4. Copper-catalyzed [3+3] reaction to synthesize pyridines or pyridones containing fluoro-atom

Scheme 5. Proposed mechanism for copper(Ⅰ)-catalyzed [3+3] reaction to synthesize pyridines or pyridones containing fluoro-atom

Scheme 6. Copper-catalyzed N—O bond cleavage and annulation cascade reaction

Scheme 7. Copper-catalyzed N—O bond cleavage and cycloaddition

Scheme 8. Proposed mechanism for copper-catalyzed amination of alkenes

Scheme 9. Copper-catalyzed N—O bond cleavage to synthesize chiral pyrrolines

Table 1. Copper-catalyzed N—O/C—C bond cleavage to synthesize alkylnitriles

Scheme 10. Proposed mechanism of copper-catalyzed N—O/ C—C bond cleavage to synthesize alkylnitriles

Scheme 11. Copper-catalyzed N—O/C—C bond cleavage to synthesize alkylnitriles

Scheme 12. Copper-catalyzed cyanoalkylarylation of activated alkenes

Scheme 13. Copper-catalyzed N—O/C—C bond cleavage to synthesize thioether compounds

Scheme 14. Copper/visible light-catalyzed N—O/C—C bond cleavage to synthesize alkylnitriles

Scheme 15. Copper-catalyzed oxime ester with trifluoromethyl- sulfonate reaction

Scheme 16. Copper-catalyzed N—O bond cleavage/C—S bond formation to synthesize substituted azetidines

Figure 1. Copper-catalyzed N-aryl nitrones to synthesize α, β-epoxyketimines

Scheme 18. Copper or gold catalyzed azido-diynes to synthesize controllable N-heterocycles

Table 3. Cu/Fe-cocatalyzed N—O bond cleavage to synthesize fused pyrroles

Table 4. Copper-catalyzed kinetic resolution of nine-membered N-heterocycles

Table 5. Cu/Fe-cocatalzyed N—O bond cleavage to synthesize pyrroles

Table 6. Co/Cu-cocatalzyed C—H bond activation

Table 7. Copper-catalyzed N—O bond cleavage to synthesize quinolones

Scheme 19. Proposed mechanism of copper (Ⅱ)-catalyzed N—O bond cleavage to synthesize quinolines

Scheme 20. synthesis of 2, 2-bipyridines via N—O bond cleavage

Table 8. Copper-catalyzed N—O cleavage to prepare N-alkenyl oxiranylketimines

Scheme 21. Proposed mechanism of copper-catalyzed N—O bond cleavage to prepare N-alkenyl oxiranylketimines

Scheme 22. Copper-catalyzed regiodivergent aminoboration of unactivated terminal alkenes

Table 9. Copper-catalyzed asymmetric dearomatization of benzofurans

Table 10. Copper-catalyzed asymmetric hydrogenamination of alkenes

Table 11. Rh/Copper-cocatalzyed C—H bond activation

Scheme 23. N—O bond cleavage to total synthesis of ezetimibe

Scheme 24. N—O bond cleavage to total synthesis of gelsemoxonine

Scheme 25. N—O bond cleavage to total synthesis of palhinines A and D

Scheme 26. N—O bond cleavage to total synthesis of huperzine R

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