Recent Advances in Transition-Metal-Catalyzed C—H Activation of Pyridone/Isoquinolones

doi:10.6023/cjoc202202017

Abstract

Pyridones/isoquinolones are a kind of important nitrogen-containing heterocyclic compounds, which have good biological activity and unique chemical properties, and play an important role in synthesis chemistry, functional materials, biomedicine and so on. Recently, transition-metal-catalyzed C—H activation has emerged as a more atom- and step-economi- cal strategy for the construction of functionalized pyridones/isoquinolones, and it has attracted the attention of many organic chemists. Herein, the recent advances in transition-metal-catalyzed C—H activation of pyridone/isoquinolone derivatives are summarized according to the types of metal catalysis. An emphasis on the discussion of catalytic system, reaction mechanisms, substrate scopes and synthetic applications is also introduced. Finally, the limitations and development trend of this research field are analyzed and prospected.

Key words: transition-metal-catalysis, pyridone, isoquinolone, C—H activation

Cite this article

Cheng Gong, Jian Tang, Fei Xu, Pengjie Li, Zetian Wang, Yumin Zhang, Guoxian Yu, Liang Wang. Recent Advances in Transition-Metal-Catalyzed C—H Activation of Pyridone/Isoquinolones[J]. Chinese Journal of Organic Chemistry, 2022, 42(7): 1925-1949.

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Fig. & Tab. 34

Figure 1. Biologically active pyridones/isoquinolones

Scheme 1. Proposed mechanism of the Mn-catalyzed C—H difluoroallylation

Scheme 2. Proposed mechanism of the Mn-catalyzed domino C—H activation/Diels-Alder/retro-Diels-Alder

Scheme 3. Manganese-catalyzed C—H alkenylation of 2-pyridones and alkynes

Scheme 4. Synthetic applications of the Mn-catalyzed C—H alkenylation

Scheme 5. Manganese-catalyzed C—H alkylation of 2-pyridone with maleimide

Scheme 6. Proposed mechanism of the Co-catalyzed domino C—H activation/directing group migration/alkyneannulation

Scheme 7. Proposed mechanism of the Co-catalyzed C—H alkenylation

Scheme 8. Nickel-catalyzed intramolecular C—H alkylation of 2-pyridones

Scheme 9. Nickel-catalyzed Enantioselective C—H alkylation of 2-pyridones

Scheme 10. Proposed mechanism of the Ni-catalyzed C—H alkylation

Scheme 11. Cu(II)-catalyzed C—H thiolation of 2-pyridones and disulfides

Scheme 12. Proposed mechanism of the Ru-catalyzed C—H amidation

Scheme 13. Proposed mechanism of the Ru-catalyzed C—H acylmethylation

Scheme 14. Rh(III)-catalyzed C—H alkylation of pyridones with diazo compounds

Scheme 15. Proposed mechanism of the Rh-catalyzed C—H alkenylation of 2-pyridones with sulfonyltriazoles

Scheme 16. Rhodium-catalyzed C—H alkenylation of 2-pyridones with conjugated carboxylic acids

Scheme 17. Proposed mechanism of the Rh-catalyzed C—H alkenylation of 2-pyridones with alkenyl carboxylic acids

Scheme 18. Proposed mechanism of the Rh-catalyzed C—H alkenylation of isoquinolin-1(2H)-ones with methylenecyclopropanes

Scheme 19. Rhodium(III)-catalyzed C—H bond functionalization of 2-pyridones with alkynes

Scheme 20. Proposed mechanism of the Rh-catalyzed C—H activation of 2-pyridones with alkynes

Scheme 21. Rhodium-catalyzed C(6)—H arylation of 2?pyridones and quinone diazides

Scheme 22. Rhodium-catalyzed C(6)-selective oxidative C—H/ C—H crosscoupling of 2-pyridones with thiophenes

Scheme 23. Proposed mechanism of the Rh-catalyzed dihydrogenative cross-coupling of 2-pyridones with thiophenes

Scheme 24. Rhodium-catalyzed annulation of 2-pyridinones with alkynes

Scheme 25. Proposed mechanism of the Rh-catalyzed C—H annulation of 2-pyridinones with alkynes

Scheme 26. Proposed mechanism of the Rh-catalyzed C—H alkynylation

Scheme 27. Proposed mechanism of the Rh-catalyzed C—H borylation

Scheme 28. Proposed mechanism of the Rh-catalyzed C—H acetoxylation

Scheme 29. Palladium-catalyzed C—H arylation of 2?pyridone with aryl iodides

Scheme 30. Palladium-catalyzed cross-coupling of 4-hydroxy- 2-pyridones with tosylhydrazones

Scheme 31. Proposed mechanism of the Pd-catalyzed C—H activation of 4-hydroxy-2-pyridones with tosylhydrazones

Scheme 32. Proposed mechanism of the Ir-catalyzed C—H amination

Scheme 33. Proposed mechanism of the Au-catalyzed C—H alkynylation

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近年来过渡金属催化吡啶酮/异喹啉酮的C—H活化反应研究进展