光/电化学合成在喹喔啉-2(1H)-酮C—H键官能化中的应用

doi:10.6023/cjoc202103032

摘要/Abstract

喹喔啉-2(1H)-酮是一类重要的含氮杂环化合物, 具有很强的生物活性与化学特性, 在合成化学、功能材料及药物工业等方面具有重要应用. 近年来, 通过C—H官能化构建3-官能化的喹喔啉-2(1H)-酮引起了很多学者的关注, 并取得了重要进展. 其中, 基于绿色化学导向的光催化及电化学合成正成为喹喔啉-2(1H)-酮的C—H官能化的强有力工具. 鉴于光电化学在合成化学中的巨大影响, 总结了可见光催化与电化学合成实现喹喔啉-2(1H)-酮3位C—H官能化的研究现状, 希望能促进绿色合成策略在含氮杂环官能化中的进一步发展.

关键词: 喹喔啉-2(1H)-酮, 可见光, 电化学, C—H官能化

Quinoxalin-2(1H)-ones are a kind of important nitrogen-containing heterocyclic compounds, which have strong biological activity and chemical properties, and play an important role in synthesis chemistry, functional materials, drugs and so on. In recent years, the construction of 3-functionalized quinoxalin-2(1H)-one by C—H functionalization has attracted the attention of many scholars and made important progress. Among them, green chemistry oriented photocatalysis and electrochemical synthesis are becoming powerful tools for C—H functionalization of quinoxaline-2(1H)-one. In view of the great influence of photochemistry in synthetic chemistry, the research status of C—H functionalization of quinoxaline- 2(1H)-one in visible light catalysis and electrochemical synthesis is summarized, hoping to promote the further development of green synthesis strategy in the functionalization of nitrogen-containing heterocycles.

Key words: quinoxalin-2(1H)-one, visible-light, electrochemistry, C—H functionalization

引用此文

刘想, 李文, 庄灿展, 曹华. 光/电化学合成在喹喔啉-2(1H)-酮C—H键官能化中的应用[J]. 有机化学, 2021, 41(9): 3459-3481.

Xiang Liu, Wen Li, Canzhan Zhuang, Hua Cao. Application of Photochemical/Electrochemical Synthesis in C—H Functionalization of Quinoxalin-2(1H)-one[J]. Chinese Journal of Organic Chemistry, 2021, 41(9): 3459-3481.

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图/表 46

图1. 具有生物活性的3-取代喹喔啉-2(1H)-酮

Figure 1. Biologically active 3-substituted quinoxalin-2(1H)-ones

图式1. 光/电化学合成在实现喹喔啉-2(1H)-酮C—H官能化中的应用

Scheme 1. Application of photochemical/electrochemical synthesis in C—H functionalization of quinoxalin-2(1H)-one

图2. 常用光催化剂的结构

Figure 2. Structures of common photocatalysts

图式2. 可见光诱导下喹喔啉-2(1H)-酮与简单醚的交叉偶联反应

Scheme 2. Cross-coupling reaction of quinoxalin-2-(1H)-ones with simple ether induced by visible light catalysis

图式3. 光催化下喹喔啉-2(1H)-酮的氰基烷基化反应

Scheme 3. Cyanoalkylation of quinoxalin-2(1H)-ones induced by visible light catalysis

图式4. 光催化下喹喔啉-2(1H)-酮的氰基烷基化反应

Scheme 4. Cyanoalkylation of quinoxalin-2(1H)-ones induced by visible light catalysis

图式5. 可见光诱导喹喔啉-2(1H)-酮的氰基烷基化反应

Scheme 5. Visible-light-induced cyanoalkylation of quinoxalin-2(1H)-ones

图式6. 光催化下喹喔啉-2(1H)-酮的区域选择烷基化反应

Scheme 6. Regioselective alkylation of quinoxalin-2-(1H)-ones under visible light catalysis

图式7. 可见光诱导喹喔啉-2(1H)-酮的区域选择性脱羧烷基化反应

Scheme 7. Visible light-induced regioselective decarboxylative alkylation of quinoxalin-2(1H)-ones

图式8. 可见光诱导喹喔啉-2(1H)-酮的区域选择性脱羧烷基化反应

Scheme 8. Visible light-induced regioselective decarboxylative alkylation of quinoxalin-2(1H)-ones

图式9. 喹喔啉-2(1H)-酮的可见光诱导脱羧烷基化反应

Scheme 9. Visible-light induced decarboxylative alkylation of quinoxalin-2(1H)-ones

图式10. 喹喔啉-2(1H)-酮的可见光诱导烷基化反应

Scheme 10. Visible-light-induced alkylation of quinoxalin- 2(1H)-ones

图式11. 光催化下喹喔啉-2(1H)-酮与醚的交叉脱氢偶联反应

Scheme 11. Cross dehydrogenative coupling reaction between quinoxalin-2(1H)-ones and ethers induced by visible light

图式12. 光催化下喹喔啉-2(1H)-酮的全氟烷基化反应

Scheme 12. Perfluoroalkylation of quinoxalin-2(1H)-ones induced by visible light

图式13. 电子催化非活化烯烃的光引发三组分α-全氟烷基-β-杂芳基化反应

Scheme 13. Photoinitiated three-component α-perfluoroalkyl-β- heteroarylation of unactivated alkenes via electron catalysis

图式14. 无光催化剂条件下可见光诱导喹喔啉-2(1H)-酮的自催化三氟甲基化反应

Scheme 14. Visible-light-induced self-catalyzed trifluoromethylation of quinoxalin-2(1H)-ones under photocatalyst free conditions

图式15. 喹喔啉-2(1H)-酮的可见光光解和有机胺催化C-3二氟烷基化反应

Scheme 15. Visible-light photoredox and organoamine catalysis for the C-3 difluoroalkylation of quinoxalin-2(1H)-ones

图式16. 可见光照射下喹喔啉-2(1H)酮类化合物的双乙酰加速C-3氢烷基化反应

Scheme 16. BI-OAc-accelerated C(3)—H alkylation of quinoxalin-2(1H)-ones under visible-light irradiation

图式17. 光催化下喹喔啉-2(1H)-酮的直接碳氢氟甲基化反应

Scheme 17. Direct C—H difluoromethylation of quinoxalin-2(1H)-ones via organic photoredox catalysis

图式18. 喹喔啉-2(1H)-酮与2,2-二氟-2-芳基乙酸钾的光引发脱羧C(3)-二氟芳基甲基化反应

Scheme 18. Photoinitiated decarboxylative C(3)-difluoro- arylmethylation of quinoxalin-2(1H)-ones with potassium 2,2-difluoro-2-arylacetates

图式19. 可见光诱导喹喔啉-2(1H)-酮与芳基重氮盐的3-芳基化

Scheme 19. Visible-light-induced 3-arylation of quinoxalin- 2(1H)-ones with aryl diazonium salts

图式20. 可见光光催化喹喔啉-2(1H)-酮与芳基重氮盐的芳基化反应

Scheme 20. Visible light photoredox-catalyzed arylation of quinoxalin-2(1H)-ones with aryldiazonium salts

图式21. 可见光促进吖啶红催化α-氧代羧酸与喹喔-2(1H)酮的有氧氧化脱羧酰化反应

Scheme 21. Visible-light-promoted acridine red catalyzed aerobic oxidative decarboxylative acylation of α-oxo-carboxylic acids with quinoxalin-2(1H)-ones

图式22. 喹喔啉-2(1H)-酮与α-氧代羧酸的可见光诱导脱羧酰化反应

Scheme 22. Visible-light-induced decarboxylative acylation of quinoxalin-2(1H)-ones with α-oxo carboxylic acids

图式23. 光催化下喹喔啉-2(1H)-酮的酰基化反应

Scheme 23. Acylation of quinoxalin-2(1H)-ones under visible light catalysis

图式24. 喹喔啉-2(1H)-酮与芳基酰基过氧化物的可见光诱导脱羧芳基化反应

Scheme 24. Visible-light-induced decarboxylation of quinoxalin-2(1H)-ones with aryl peroxide

图式25. 可见光光催化下喹喔啉-2(1H)-酮与脂肪胺的交叉脱氢偶联

Scheme 25. Cross-dehydrogenative coupling of quinoxalin-2(1H)-ones with aliphatic amines under visible-light catalysis

图式26. 可见光引发的喹喔啉-2(1H)酮与简单酰胺的交叉脱氢偶联

Scheme 26. Visible-light-initiated cross-dehydrogenative coupling of quinoxalin-2(1H)-ones and simple amides

图式27. 无光敏剂参与的可见光光解催化喹喔啉-2(1H)-酮与唑的碳氮偶联反应

Scheme 27. Visible-light photoredox catalyzed C—N coupling of quinoxaline-2(1H)-ones with azoles without external photosensitizer

图式28. 可见光诱导下喹喔啉-2(1H)-酮与醇的烷氧基化反应

Scheme 28. Visible-light-induced alkoxylation of quinoxalin-2(1H)-ones with alcohols

图式29. 光催化下喹喔啉酮的(硫)醚化反应

Scheme 29. (Thio)etherification of quinoxalinones under visible-light photoredox catalysis

图式30. 可见光诱导喹喔啉-2(1H)-酮与氟烷基醇的氟烷氧基化反应

Scheme 30. Visible-light-induced fluoroalkoxylation of quinoxalin-2(1H)-ones with fluoroalkyl alcohols

图式31. 可见光催化下喹喔啉-2(1H)-酮与醇的交叉脱氢偶联反应

Scheme 31. Cross-dehydrogenative coupling of quinoxalin- 2(1H)-ones with alcohols under visible-light catalysis

图式32. 可见光诱导无光催化剂条件下喹喔啉-2(1H)-酮与硫醇的直接碳氢亚磺酰化反应

Scheme 32. Direct C—H sulfenylation of quinoxalin-2(1H)- ones with thiols under visible-light-induced photocatalyst-free conditions

图式33. 可见光促进的喹喔啉-2(1H)-酮与硫醇的直接碳-氢/硫-氢交叉偶联反应

Scheme 33. Visible-light-promoted direct C—H/S—H cross- coupling of quinoxalin-2(1H)-ones with thiols

图式34. 可见光光解催化喹喔啉-2(1H)酮的磷酸化反应

Scheme 34. Visible light photoredox-catalyzed phosphorylation of quinoxalin-2(1H)-ones

图式35. 光催化下喹喔啉-2(1H)-酮的硅烷化反应

Scheme 35. Silylation of quinoxalin-2(1H)-ones under visible light catalysis

图式36. 电化学下喹喔啉-2(1H)-酮的三氟甲基化反应

Scheme 36. Trifluoromethylation of quinoxalin-2(1H)-ones under electrochemical conditions

图式37. 喹喔啉-2(1H)-酮与N-羟基邻苯二甲酰亚胺酯的电化学脱羧C-3烷基化反应

Scheme 37. Electrochemical decarboxylative C-3 alkylation of quinoxalin-2(1H)-ones with N-hydroxyphthalimide esters

图式38. 电化学下喹喔啉-2(1H)-酮的脱氧烷基化反应

Scheme 38. Deoxyalkylation of quinoxalin-2(1H)-ones under electrochemical conditions

图式39. 电化学下喹喔啉-2(1H)-酮的C-3吡啶化反应

Scheme 39. Electrochemical C-3 pyridination of quinoxalin- 2(1H)-ones

图式40. 喹喔啉-2(1H)-酮与有机硼化合物的电催化氧化碳氢烷基化反应

Scheme 40. Electro-oxidative C—H alkylation of quinoxalin-2(1H)-ones with organoboron compounds

图式41. 喹喔啉-2(1H)-酮与胺的电化学脱氢交叉偶联反应

Scheme 41. Electrochemical dehydrogenative cross-coupling of quinoxalin-2(1H)-ones with amines

图式42. 电化学下喹喔啉-2(1H)-酮的C-3烷氧基化反应

Scheme 42. Electrochemical C-3 alkoxylation of quinoxalin-2(1H)-ones

图式43. 喹喔啉-2(1H)-酮与硫醇的电化学氧化交叉偶联

Scheme 43. Electrochemically oxidative cross-coupling between quinoxalin-2(1H)-ones and thiols

图式44. 电化学下喹喔啉-2(1H)-酮的磷酸化反应

Scheme 44. Electrochemical phosphorylation of quinoxalin-2 (1H)-ones

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