交叉脱氢偶联反应构建碳-碳键的可替代策略

doi:10.6023/cjoc202009053

摘要/Abstract

交叉脱氢偶联(CDC)反应是一种直接、有效的形成碳-碳键的方法. 这些反应通常在溶液体系中经外界加热搅拌进行. 随着新型合成方法的发展, 目前实验室中可用于促进CDC反应的替代技术, 如光化学、电化学和机械化学技术迅速兴起, 这些方法作为传统热化学法的完美补充, 为碳-碳键的构建提供了绿色、高效的策略. 对比综述了相同或相似底物参与的两种或两种以上CDC反应激发策略, 希望能够对CDC反应的发展及有机合成新方法的开发提供帮助.

关键词: 交叉脱氢偶联反应, 热化学, 光化学, 电化学, 机械化学

Cross-dehydrogenative coupling (CDC) reactions have been esteemed as one of the straightforward and efficient tool for C—C bond formation. Typically, these reactions are generally realized via solvent-based thermochemistry, using a round bottom flask and a magnetic or mechanical stirrer. With the development of new synthetic strategies, alternative technologies currently available in laboratories that facilitate CDC reactions, such as photochemistry, electrochemistry and mechanochemistry have arisen rapidly, providing green and high efficiency strategies for the construction of C—C bonds which are perfect complement to traditional thermochemistry. In order to compare the advantages of each approaches more clearly, and promote the development of CDC reactions, CDC reactions related to two or more enabling technologies of same or similar substrates are reviewed, hoping to provide help for the development of CDC reaction and the development of new organic synthesis methods.

Key words: cross-dehydrogenative coupling, thermochemistry, photochemistry, electrochemistry, mechanochemistry

引用此文

王浩, 应娉, 俞静波, 苏为科. 交叉脱氢偶联反应构建碳-碳键的可替代策略[J]. 有机化学, 2021, 41(5): 1897-1924.

Hao Wang, Ping Ying, Jingbo Yu, Weike Su. Alternative Strategies Enabling Cross-Dehydrogenative Coupling: Access to C—C Bonds[J]. Chinese Journal of Organic Chemistry, 2021, 41(5): 1897-1924.

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图/表 45

图式1. 交叉脱氢偶联反应构建C—C键的可替代策略

Scheme 1. Alternative strategies access to C—C bond via CDC reactions

图式2. C(sp3)—H亲电底物参与的交叉脱氢偶联反应

Scheme 2. CDC reactions for C(sp3)—H electrophilic substrates

图式3. 四氢异喹啉与硝基烷烃的CDC反应(MM=mix miller)

Scheme 3. CDC reactions of tetrahydroisoquinolines with nitromethane (MM=mix miller)

图式4. 光催化下四氢异喹啉与硝基甲烷的CDC反应机理

Scheme 4. Proposed mechanism for CDC reaction of tetrahydroisoquinoline and nitromethane under photocatalysis

图式5. 四氢异喹啉与烷基酮的CDC反应

Scheme 5. CDC reactions of tetrahydroisoquinolines with ketones

图式6. VO(acac)2与有机催化剂协同催化四氢异喹啉与烷基酮的CDC反应机理(L=acetyl acetonate)

Scheme 6. Proposed mechanism for CDC reaction of tetrahydroisoquinolines and ketones catalyzed by synergetic vanadium- and organocatalysis (L=acetyl acetonate)

图式7. 四氢异喹啉与醛、酮的不对称CDC反应

Scheme 7. Asymmetric CDC reactions of tetrahydroisoquinolines with aldehydes and ketones

图式8. N-酰基取代四氢异喹啉与醛的不对称CDC反应底物范围

Scheme 8. Substrates scope of asymmetric CDC reactions of N-carbamoyl tetrahydroisoquinolines with aldehydes

图式9. 四氢异喹啉与酮的不对称CDC反应机理

Scheme 9. Proposed mechanism for asymmetric CDC reactions of tetrahydroisoquinolines with ketones

图式10. 可见光照射下Ru/Co共催化促进亚胺形成机理

Scheme 10. Proposed mechanism for the formation of imine promoted by Ru/Co cocatalysis under visible light irradiation

图式11. 四氢异喹啉及其类似物与酸性亚甲基化合物的CDC反应

Scheme 11. CDC reactions of tetrahydroisoquinolines and analogues with acidic methylenes

图式12. 甘氨酸酯与β-酮酯的CDC反应

Scheme 12. CDC reactions of glycine ester with β-ketoesters

图式13. 3-苄基吲哚与1,3-二羰基化合物的CDC反应

Scheme 13. CDC reactions of 3-benzylic indoles with 1,3-dicarbonyls

图式14. 液体辅助研磨下3-苄基吲哚与1,3-二羰基化合物的不对称CDC反应机理

Scheme 14. Plausible asymmetric CDC reaction mechanism by liquid-assisted grinding between 3-benzylic indoles and 1,3-dicarbonyls

图式15. 氧杂蒽类化合物与醛的不对称CDC反应

Scheme 15. Asymmetric CDC reactions of xanthenes with aldehydes

图式16. 电化学催化氧杂蒽与醛的不对称CDC反应机理

Scheme 16. Prosposed mechanism for asymmetric CDC reactions of xanthenes with aldehydes by electrocatalysis

图式17. 光催化氧杂蒽与醛的不对称CDC反应列举

Scheme 17. Selected examples of asymmetric CDC reactions of xanthenes with aldehydes by photoocatalysis

图式18. 四氢异喹啉与吲哚的CDC反应(MM=mix miller)

Scheme 18. CDC reactions of tetrahydroisoquinolines with indoles (MM=mix miller)

图式19. 四氢异喹啉与唑类化合物的CDC反应

Scheme 19. CDC reactions of tetrahydroisoquinolines with azoles

图式20. 光催化四氢异喹啉与唑类化合物的CDC反应底物范围列举

Scheme 20. Selected examples for CDC reactions of tetrahydroisoquinolines with azoles catalyzed by photocatalysis

图式21. 甘氨酸衍生物与吲哚的CDC反应

Scheme 21. CDC reactions of glycine derivatives with indoles

图式22. α-取代甘氨酸衍生物与吲哚的反应

Scheme 22. Reactions of α-substituted glycine derivatives with indoles

图式23. 热化学下α-取代甘氨酸衍生物与吲哚CDC反应机理

Scheme 23. Proposed mechanism for CDC reaction of α-substituted glycine derivatives with indoles by external heating/stirring

图式24. 光催化下α-取代甘氨酸衍生物与吲哚的不对称Friedel-Crafts反应机理

Scheme 24. Proposed mechanism for asymmetric Friedel-Crafts reaction of α-substituted glycine derivatives with indoles by photocatalysis

图式25. 甘氨酸衍生物与酚、萘酚的CDC反应

Scheme 25. CDC reactions of glycine derivatives with phenols and naphthols

图式26. 甘氨酸酯与芳基酚的CDC反应底物范围列举

Scheme 26. Selected examples for CDC reactions of glycine derivatives with phenols

图式27. 甘氨酸衍生物与唑类化合物的CDC反应

Scheme 27. CDC reactions of glycine derivatives with azoles

图式28. 甘氨酸衍生物与N-取代苯胺的CDC反应

Scheme 28. CDC reactions of glycine derivatives with N-sub- stituted anilines

图式29. 环(杂)烷烃与唑类化合物的CDC反应

Scheme 29. CDC reactions of cyclo(hetero)alkanes with azoles

图式30. 热化学条件下环醚与唑类化合物的CDC反应机理

Scheme 30. Proposed mechanism for CDC reaction of cyclic ethers with azoles under external heating/stirring

图式31. 可见光下N-Boc-吡咯烷与唑类化合物的CDC反应机理

Scheme 31. Proposed mechanism for CDC reaction of N-Boc-pyrrolidine with azoles under visible light irradiation

图式32. 光催化N-Boc-吡咯烷与唑类化合物的CDC反应底物范围及药物结构修饰

Scheme 32. Substrate scope for CDC reaction of N-Boc-pyrrolidine and azoles and the modification of drug structure

图式33. 2(1H)-喹喔啉酮与醚的CDC反应

Scheme 33. CDC reactions of quinoxalin-2(1H)-ones with ethers

图式34. 四氢异喹啉与炔烃的CDC反应

Scheme 34. CDC reactions of tetrahydroisoquionolines with alkynes

图式35. Fe/Zn双金属催化四氢异喹啉与炔烃的不对称CDC反应底物范围列举

Scheme 35. Selected examples of asymmetric CDC reaction of tetrahydroisoquionolines with alkynes by Fe/Zn catalysis

图式36. Fe/Zn双金属催化四氢异喹啉与炔烃的不对称CDC反应机理

Scheme 36. Proposed mechanism for asymmetric CDC reaction of tetrahydroisoquionolines with alkynes catalyzed by Fe/Zn catalysis

图式37. 芳酚与芳烃的CDC反应

Scheme 37. CDC reactions of phenols with arenes

图式38. 电催化芳酚与芳烃的CDC反应机理

Scheme 38. Proposed mechanism for CDC reaction of phenol with arene by electrocatalysis

图式39. 光催化芳酚与芳烃的CDC反应底物范围

Scheme 39. Substrate scope for CDC reactions of phenol with arene by photocatalysis

图式40. 苯胺与苯胺的CDC反应

Scheme 40. CDC reactions of two anilines

图式41. 电催化CDC反应实现药物分子官能团化修饰

Scheme 41. CDC reactions for functional modification of drug molecules by electrocatalysis

图式42. 芳酚与苯胺的CDC反应

Scheme 42. CDC reactions of phenols with anilines

图式43. N-芳基烯胺的分子内CDC反应

Scheme 43. Intramolecular CDC reactions of N-aryl enamines

图式44. 异喹啉与醛的CDC反应

Scheme 44. CDC reactions of isoquinolines with aldehydes

图式45. 异喹啉与醛的CDC反应制备天然生物碱

Scheme 45. Alkaloids synthesis by CDC reaction of isoquinolines with aldehydes

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