烯烃参与的还原Heck反应构建C(sp2)—C(sp3)键研究进展

doi:10.6023/cjoc202105016

摘要/Abstract

过渡金属催化的C(sp²)—C(sp³)交叉偶联在有机合成中具有重要意义, 可用于合成复杂天然产物和药物分子. 近年来, 还原Heck反应已发展成为构筑C(sp²)—C(sp³)键的简洁、高效方法之一. 根据参与反应的氢供体类型不同, 综述了近十年来烯烃参与还原Heck反应的研究进展. 对其作用机理进行了阐述, 并对该领域的未来发展进行了展望.

关键词: 烯烃, 过渡金属催化, 还原Heck反应, C(sp²)—C(sp³)键构建

Transition-metal catalyzed C(sp²)—C(sp³) cross-coupling is of great significance in organic chemistry for synthesizing complex natural products and pharmaceutical molecules. Recently, reductive Heck reactions have emerged as one of the simple and efficient strategies for the construction of C(sp²)—C(sp³) bond. The recent advances in the reductive Heck reactions of alkenes are summarized on the basis of different hydride sources. The related mechanisms are provided, and the future development of this field is also prospected.

Key words: alkene, transition-metal catalysis, reductive Heck reaction, C(sp²)—C(sp³) formation

引用此文

肖霄, 刘建超. 烯烃参与的还原Heck反应构建C(sp²)—C(sp³)键研究进展[J]. 有机化学, 2021, 41(9): 3349-3365.

Xiao Xiao, Jianchao Liu. Progress in the Synthesis of C(sp²)—C(sp³) Bond by Reductive Heck Reactions of Alkenes[J]. Chinese Journal of Organic Chemistry, 2021, 41(9): 3349-3365.

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图/表 30

图式1. 还原Heck反应机理

Scheme 1. Mechanism for the reductive Heck reaction

图式2. (–)-lycoramine 和(–)-galanthamine的合成

Scheme 2. Syntheses of (–)-lycoramine and (–)-galanthamine

图式3. (+)-PI-220和(+)-3-epi-furaquinocin C的合成

Scheme 3. Syntheses of (+)-PI-220 and (+)-3-epi-furaquinocin C

图式4. 通过还原Heck反应合成吲哚啉

Scheme 4. Indoline synthesis via the reductive Heck reaction

图式5. 钯催化吲哚去芳构化的还原Heck反应机理

Scheme 5. Proposed mechanism for palladium-catalyzed dearomative reductive Heck reaction of indoles

图式6. 钯催化1,3-二烯的1,2-氢烯基化反应机理

Scheme 6. Proposed mechanism for palladium-catalyzed 1,2- hydrovinylation of 1,3-dienes

图式7. 通过还原Heck型环化反应合成四氢吡啶

Scheme 7. Tetrahydropyridines synthesis via the reductive Heck cyclization

图式8. 钯催化烯烃的分子间氢芳基化反应

Scheme 8. Palladium-catalyzed intermolecular hydroarylation of alkenes

图式9. 钯催化烯烃的分子间氢芳基化反应的可能机理

Scheme 9. Proposed mechanism for palladium-catalyzed intermolecular hydroarylation of alkenes

图式10. 瞬态导向烯烃的还原Heck反应可能机理

Scheme 10. Proposed mechanism for transiently directed reductive Heck reaction of alkenes

图式11. 钯催化烯丙基芳基醚的分子内还原Heck反应

Scheme 11. Palladium-catalyzed intramolecular Heck reaction of allyl aryl ethers

图式12. 钯催化环戊烯的不对称还原Heck去对称化

Scheme 12. Palladium-catalyzed asymmetric reductive Heck desymmetrization of cyclopentenes

图式13. Mizoroki-Heck和还原Heck串联反应的机理

Scheme 13. Proposed mechanism for the Mizoroki-Heck/reductive Heck cascade reactions

图式14. 钯催化硫酯的不对称还原Heck反应

Scheme 14. Palladium-catalyzed asymmetric reductive Heck reaction of thioesters

图式15. 通过不对称还原Heck反应合成手性茚酮

Scheme 15. Synthesis of chiral indanones based upon an asymmetric reductive Heck reaction

图式16. 还原Heck反应与Mizoroki-Heck反应的竞争

Scheme 16. Reductive Heck reaction versus the Mizoroki-Heck reaction

图式17. 钯催化芳基氯代烃的不对称还原Heck反应

Scheme 17. Palladium-catalyzed asymmetric reductive Heck reaction of aryl halides

图式18. 亚磷酰胺配体参与的不对称还原Heck反应

Scheme 18. Asymmetric reductive Heck reaction with monodentate phosphoramidite ligand

图式19. 钯催化非活化烯烃的还原Heck反应

Scheme 19. Palladium catalyzed reductive Heck reaction of unactivated alkenes

图式20. 非活化烯烃还原Heck反应的可能机理

Scheme 20. Proposed mechanism for the reductive Heck reaction of unactivated alkenes

图式21. 钯催化α,β-不饱和酯的逆Michael还原Heck反应

Scheme 21. Palladium catalyzed anti-Michael reductive Heck reaction of α,β-unsaturated esters

图式22. 钯催化α,β-不饱和酮与芳基碘的还原Heck反应

Scheme 22. Palladium catalyzed reductive Heck reaction of α,β- unsaturated ketones with aryl iodides

图式23. 钯催化非活化烯烃和芳基溴的还原Heck反应

Scheme 23. Palladium catalyzed reductive Heck reaction of inactivated olefins with aryl bromides

图式24. 非活化烯烃和芳基溴的还原Heck反应机理

Scheme 24. Proposed mechanism for the reductive Heck reaction of inactivated olefins with aryl bromides

图式25. 非活化脂肪族烯烃和有机卤代烃的还原Heck反应

Scheme 25. Reductive Heck reaction of unactivated aliphatic alkenes with organohalides

图式26. 镍催化非活化烯烃的不对称还原Heck反应

Scheme 26. Nickel-catalyzed asymmetric reductive Heck reaction of inactivated olefins

图式27. 反马氏选择性的还原Heck反应

Scheme 27. Anti-Markovnikov selective reductive Heck reaction

图式28. 水作为氢源的还原Heck反应

Scheme 28. Reductive Heck reaction using water as a hydride source

图式29. 钯催化的不对称还原Heck反应机理

Scheme 29. Proposed mechanism for Pd-catalyzed asymmetric reductive Heck reaction

图式30. 镍催化的不对称还原Heck反应

Scheme 30. Nickel-catalyzed asymmetric reductive Heck reaction

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烯烃参与的还原Heck反应构建C(sp²)—C(sp³)键研究进展

Progress in the Synthesis of C(sp²)—C(sp³) Bond by Reductive Heck Reactions of Alkenes

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