Recent Progress in Transition Metal-Catalyzed C—H Bond Activation of N-Aryl Phthalazinones

doi:10.6023/cjoc202204056

Abstract

N-Aryl phthalazinones are important nitrogen heterocycles widely existing in the natural products and drug molecules. Meanwhile, N-aryl phthalazinones are also very significant substrates for organic synthesis. In recent years, with the development of C—H bond activation catalyzed by transition metal, the synthesis of nitrogen heterocycles via the C—H bond cleavage of phthalazines derivatives has attracted attention of chemists. In this paper, the recent progress of the transition metal-catalyzed C—H bond activation reaction of phthalazines is reviewed by classifying different coupling components, and the reaction mechanism is discussed.

Key words: N-aryl phthalazinones, transition metal, C—H bond activation, coupling partners

Cite this article

Haichun Gu, Xinxin Jin, Jiaqi Li, He Li, Jinglin Liu. Recent Progress in Transition Metal-Catalyzed C—H Bond Activation of N-Aryl Phthalazinones[J]. Chinese Journal of Organic Chemistry, 2022, 42(9): 2682-2702.

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Fig. & Tab. 32

Figure 1. Selected examples for phthalazinone bioactive molecules

Scheme 1. Ru-catalyzed regio-selective annulation

Scheme 2. A plausible mechanism for Ru-catalyzed regio-selective annulation of N-aryl phthalazinones with propargyl alcohols

Scheme 3. Rh-catalyzed [4+1] annulation of N-aryl phthalazinones with propargyl alcohols

Scheme 4. Rh-catalyzed C—H/N—H annulation of N-aryl phthalazinones with alkyne

Scheme 5. A plausible mechanism for Rh-catalyzed C—H/N—H annulation of N-aryl phthalazinones with alkyne

Scheme 6. Ru-catalyzed annulation of N-aryl phthalazinones with alkynes

Scheme 7. A possible mechanism for Ru-catalyzed annulation of N-aryl phthalazinones with alkynes

Scheme 8. Ru-catalyzed annulation of N-aryl phthalazinedione with acrylates

Scheme 9. A plausible mechanism for Ru-catalyzed annulation of N-aryl phthalazinediones with acrylates

Scheme 10. Synthesis of cinnolines via Rh-catalyzed annulation of N-aryl phthalazinediones with vinylene carbonate

Scheme 11. A possible mechanism for synthesis of cinnolines via Rh-catalyzed annulation of N-aryl phthalazinediones with vinylene carbonate

Scheme 12. Rh-catalyzed C—H functionalization of N-aryl phthalazinone with succinimide

Scheme 13. Plausible mechanism for Rh-catalyzed C—H functionalization of N-aryl phthalazinones with maleimides

Scheme 14. Rhodium-catalyzed spirocyclization of N-aryl phthalazinones with maleimide

Scheme 15. A possible mechanism for rhodium-catalyzed spirocyclization of N-aryl phthalazinones with maleimide

Scheme 16. Rh-catalyzed annulation of N-aryl phthalazinones with β-nitroolefins

Scheme 17. A possible mechanism for Rh-catalyed annulation of N-aryl phthalazinones with β-nitroolefins

Scheme 18. Rh-catalyzed annulation of N-aryl phthalazinones with allenes

Scheme 19. A possible mechanism for Rh-catalyzed annulation of N-aryl phthalazinones with allenes

Scheme 20. Additive-driven Rh-catalyzed [4+1]/[4+2] annulations of N-aryl phthalazinones

Scheme 21. A plausible mechanism for additive-driven Rh-catalyzed [4+1]/[4+2] annulations of N-aryl phthalazinones

Scheme 22. Ir(III)-catalyzed C—H bond activation/annulation of N-aryl phthalazinones with 1,3-diketone-2-diazo

Scheme 23. Ru-catalyzed C—H bond activation of N-aryl phthalazinones with sulfur ylides

Scheme 24. Plausible mechanism for Ru-catalyzed C—H bond activation of N-aryl phthalazinones with sulfur Ylides

Scheme 25. Rh-catalyzed C—H amidation of N-aryl phthalazinones

Scheme 26. Proposed reaction mechanism for Rh-catalyzed C—H amidation of N-aryl phthalazinones

Scheme 27. Ru-catalyzed C—H bond alkylation reaction of N-aryl phthalazinones

Scheme 28. Ru-catalyzed C—H bond amidation/annulation reaction of N-aryl phthalazinones

Scheme 29. A plausible mechanism for Ru-catalyzed C—H bond amidation/annulation reaction of N-aryl phthalazinones

Scheme 30. Pd-catalyzed C—H bond halogenation and sulfonylation of N-aryl phthalazines

Scheme 31. A possible mechanism for Pd-catalyzed C—H bond halogenation and sulfonylation of N-aryl phthalazines

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