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

doi:10.6023/cjoc202202017

摘要/Abstract

吡啶酮或异喹啉-1-酮是一类重要的含氮杂环化合物, 具有良好的生物活性和独特的化学性能, 在合成化学、功能材料和生物医药等领域具有重要研究价值和应用前景. 近年来, 过渡金属催化C—H活化反应为官能化吡啶酮或异喹啉-1-酮的构建提供了一种更为原子经济和步骤经济的合成策略, 受到有机化学家们的广泛关注. 按照金属催化剂的种类进行分类, 综述了近些年过渡金属催化吡啶酮或异喹啉-1-酮衍生物的C—H活化反应的研究进展, 着重探讨了催化体系、反应机理、底物适用性及其相关应用, 并对该领域存在的问题以及发展趋势进行了分析和展望.

关键词: 过渡金属催化, 吡啶酮, 异喹啉酮, C—H活化反应

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

引用此文

龚诚, 唐剑, 徐飞, 李鹏杰, 王泽田, 张玉敏, 余国贤, 王亮. 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[J]. 有机化学, 2022, 42(7): 1925-1949.

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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图/表 34

图1. 具有生物活性的2-吡啶酮/异喹啉-1-酮

Figure 1. Biologically active pyridones/isoquinolones

图式1. 锰催化C—H二氟烯丙基化反应可能的机理

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

图式2. 锰催化串联的C—H活化/Diels-Alder(D-A)反应/逆D-A反应可能的机理

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

图式3. 锰催化2-吡啶酮与炔烃的C—H烯化反应

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

图式4. 锰催化C—H烯基化反应的合成应用

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

图式5. 锰催化2-吡啶酮和马来酰亚胺的C—H烷基化反应

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

图式6. 钴催化串联的C—H活化/导向基迁移/炔环化反应可能的机理

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

图式7. 钴催化C—H烯基化反应可能的机理

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

图式8. 镍催化2-吡啶酮的分子内C—H烷基化反应

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

图式9. 镍催化2-吡啶酮的对映选择性C—H烷基化反应

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

图式10. 镍催化C—H烷基化反应可能的机理

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

图式11. 铜催化2-吡啶酮与二硫醚的C—H巯基化反应

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

图式12. 钌催化C—H酰胺化反应可能的机理

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

图式13. 钌催化C—H酰甲基化反应可能的机

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

图式14. 铑催化吡啶酮与重氮化合物的C—H烷基化反应

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

图式15. 铑催化2-吡啶酮与磺酰基三氮唑的C—H烯基化反应可能的机理

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

图式16. 铑催化2-吡啶酮与不饱和羧酸的C—H烯化反应

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

图式17. 铑催化2-吡啶酮与不饱和羧酸的C—H烯基化反应可能的机理

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

图式18. 铑催化异喹啉-1-酮与亚甲基环丙烷的C—H烯基化反应可能的机理

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

图式19. 铑催化2-吡啶酮与炔烃的C—H官能化反应

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

图式20. 铑催化2-吡啶酮与炔烃的C—H活化反应可能的机理

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

图式21. 铑催化2-吡啶酮与醌类重氮化物的C(6)—H芳化反应

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

图式22. 铑催化2-吡啶酮与噻吩的C(6)位选择性氧化偶联反应

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

图式23. 铑催化2-吡啶酮与噻吩的脱氢-活化交叉偶联反应可能的机理

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

图式24. 铑催化2-吡啶酮与炔烃的环化反应

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

图式25. 铑催化2-吡啶酮与炔烃的C—H环化反应可能的机理

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

图式26. 铑催化C—H炔化反应可能的机理

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

图式27. 铑催化C—H硼化反应可能的机理

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

图式28. 铑催化C—H乙酰氧化反应可能的机理

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

图式29. 钯催化2-吡啶酮与碘代芳烃的C—H芳化反应

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

图式30. 钯催化4-羟基-2-吡啶酮与对甲基苯磺酰腙的交叉偶联反应

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

图式31. 钯催化4-羟基-2-吡啶酮与苯磺酰腙的C—H活化反应可能的机理

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

图式32. 铱催化C—H胺化反应可能的机理

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

图式33. 金催化C—H炔化反应可能的机理

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

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