过渡金属催化N-芳基酞嗪的C—H键活化反应研究进展

doi:10.6023/cjoc202204056

摘要/Abstract

N-芳基酞嗪是存在于天然产物及药物分子中的一种重要含氮芳香杂环化合物, 同时, 也是非常重要的有机合成原料. 近年来, 随着过渡金属催化C—H键活化研究的发展, 通过切断酞嗪衍生物的C—H键来实现制备含氮杂环化合物, 吸引了越来越多化学家们的关注. 通过对不同偶联组分的分类, 综述了近年来酞嗪参与的过渡金属催化C—H键活化反应最新研究进展, 并对反应机理进行了论述.

关键词: N-芳基酞嗪, 过渡金属, C—H键活化, 偶联组分

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

引用此文

顾海春, 靳新新, 李嘉琪, 李贺, 刘景林. 过渡金属催化N-芳基酞嗪的C—H键活化反应研究进展[J]. 有机化学, 2022, 42(9): 2682-2702.

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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图/表 32

图1. 含酞嗪骨架类药物

Figure 1. Selected examples for phthalazinone bioactive molecules

图式1. 钌催化的区域选择性环化反应

Scheme 1. Ru-catalyzed regio-selective annulation

图式2. 钌催化N-芳基酞嗪与丙炔醇的区域选择性环化反应机理

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

图式3. 铑催化N-芳基酞嗪与炔丙醇的[4+1]环化反应

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

图式4. 铑催化N-芳基酞嗪与炔烃的C—H/N—H键环化反应

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

图式5. 铑催化N-芳基酞嗪与炔烃的C—H/N—H键环化反应机理

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

图式6. 钌催化N-芳基酞嗪与炔烃的环化反应

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

图式7. 钌催化N-芳基酞嗪与炔烃的环化反应机理

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

图式8. 钌催化N-芳基酞嗪与丙烯酸甲酯的环化反应

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

图式9. 钌催化N-芳基酞嗪与丙烯酸甲酯的环化反应机理

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

图式10. 铑催化N-芳基酞嗪与碳酸乙烯酯合成噌啉的反应

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

图式11. 铑催化N-芳基酞嗪与碳酸乙烯酯合成噌啉的反应机理

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

图式12. 铑催化N-芳基酞嗪与马来酰亚胺的C—H键官能团化反应

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

图式13. 铑催化N-芳基酞嗪与马来酰亚胺的C—H键官能团化反应机理

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

图式14. 铑催化N-芳基酞嗪与马来酰亚胺的螺化反应

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

图式15. 铑催化N-芳基酞嗪与马来酰亚胺的螺化反应

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

图式16. 铑催化N-芳基酞嗪与β-硝基苯乙烯的环化反应

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

图式17. 铑催化N-芳基酞嗪与β-硝基苯乙烯的环化反应机理

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

图式18. 铑催化N-芳基酞嗪与联烯的环化反应

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

图式19. 铑催化N-芳基酞嗪与联烯的环化反应机理

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

图式20. 添加剂调控的铑催化N-芳基酞嗪参与的[4+1]/[4+2]环化反应

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

图式21. 添加剂调控的铑催化N-芳基酞嗪参与的[4+1]/[4+2]环化反应机理

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

图式22. 铱催化N-芳基酞嗪与1,3-二酮-2-重氮化合物发生C—H键活化/环化反应

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

图式23. 钌催化N-芳基酞嗪与硫叶立德参与的C—H键活化反应

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

图式24. 钌催化N-芳基酞嗪与硫叶立德参与的C—H键活化反应机理

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

图式25. 铑催化N-芳基酞嗪参与的C—H键酰胺化反应

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

图式26. 铑催化N-芳基酞嗪参与的C—H键酰胺化反应机理

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

图式27. 钌催化N-芳基酞嗪的C—H键烷基化反应

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

图式28. 钌催化N-芳基酞嗪参与的C—H键酰胺化/环化反应

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

图式29. 钌催化N-芳基酞嗪参与的C—H键酰胺化/环化反应机理

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

图式30. 钯催化N-芳基酞嗪的C—H键卤化和磺酰化反应

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

图式31. 钯催化N-芳基酞嗪的C—H键卤化和磺酰化反应机理

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

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