钯催化的烯烃异构化反应

doi:10.6023/cjoc202109045

有机化学 ›› 2022, Vol. 42 ›› Issue (3): 742-757.DOI: 10.6023/cjoc202109045 上一篇下一篇

综述与进展

钯催化的烯烃异构化反应

陈宏超^a^,^b, 吴奕晨^b, 于洋^a, 王鹏^b^,^c^,^d^,^*()

a 上海大学理学院上海 201900
b 中国科学院上海有机化学研究所金属有机化学国家重点实验室上海 200032
c 中国科学院上海有机化学研究所中国科学院能量调控材料重点实验室上海 200032
d 中国科学院大学杭州高等研究院化学与材料科学学院杭州 310024

收稿日期:2021-09-28 修回日期:2021-11-03 发布日期:2021-11-17
通讯作者: 王鹏
基金资助:
国家自然科学基金(22171277); 国家自然科学基金(22101291); 国家自然科学基金(21821002); 上海“启明星”(20QA1411400)

Pd-Catalyzed Isomerization of Alkenes

Hong-Chao Chen^a^,^b, Yichen Wu^b, Yang Yu^a, Peng Wang^b^,^c^,^d()

a College of Science, Shanghai University, Shanghai 201900
b State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Shanghai 200032
c CAS Key Laboratory of Energy Regulation Materials, Shanghai Institute of Organic Chemistry, Shanghai 200032
d School of Chemistry and Material Sciences, Hangzhou Institute for Advanced Study, University of Chinese Academy of Sciences, Hangzhou 310024

Received:2021-09-28 Revised:2021-11-03 Published:2021-11-17
Contact: Peng Wang
Supported by:
National Natural Science Foundation of China(22171277); National Natural Science Foundation of China(22101291); National Natural Science Foundation of China(21821002); Shanghai Rising-Star Program(20QA1411400)

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摘要/Abstract

烯烃异构反应可以从简单烯烃出发, 通过对碳碳双键立体选择性或者位置选择性调控, 实现内烯烃化合物尤其其他方法难以构建的多取代烯烃的高效合成, 原子经济性高. 详细介绍了钯催化烯烃异构化反应的反应机制, 系统总结了钯催化的烯烃顺反异构和位置选择性异构反应, 以及其在药物分子和天然产物合成中的应用.

关键词: 钯催化, 烯烃, 碳碳双键, 异构

Starting from commercially available simple olefins, alkene isomerization could realize the efficient construction of multi-substituted alkenes, which might be difficult to access with other synthetic methods, in an atom-economic manner via the stereoselective or positional-selective modulation of the carbon-carbon double bonds. The palladium catalyzed stereoselective (Z/E) and the positional selective isomerization reactions of alkenes are summarized. The mechanistic perspectives, and their synthetic applications in the synthesis of drug molecules and natural products are discussed in detail.

Key words: palladium catalysis, alkene, carbon-carbon bond, isomerization

引用此文

陈宏超, 吴奕晨, 于洋, 王鹏. 钯催化的烯烃异构化反应[J]. 有机化学, 2022, 42(3): 742-757.

Hong-Chao Chen, Yichen Wu, Yang Yu, Peng Wang. Pd-Catalyzed Isomerization of Alkenes[J]. Chinese Journal of Organic Chemistry, 2022, 42(3): 742-757.

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图/表 44

图式1. 烯烃的应用与转化

Scheme 1. Application and transformation of alkenes

图式2. 钯催化的烯烃异构化主要反应历程

Scheme 2. Main processes for Pd-catalyzed alkene isomerization

图式3. 烯基氯的产生途径

Scheme 3. Production pathway for vinyl chloride formation

图式4. 碳正离子中间体的验证实验

Scheme 4. Experimental studies on carbocation intermediate mechanism

图5. 经历烯丙基钯中间体的反应过程

Scheme 5. Alkene isomerization via allyl-Pd intermediate

图式6. PdCl2/FeCl3体系催化的烯烃位置异构反应

Scheme 6. PdCl2/FeCl3 catalyzed alkene migratory isomerization

图式7. Pd(TFA)2/TsOH•H2O催化的烯烃位置异构反应

Scheme 7. Pd(TFA)2/TsOH•H2O catalyzed alkene migratory isomerization

图式8. 经由钯卡宾中间体的烯烃位置异构反应

Scheme 8. Migratory isomerization of alkene via palladium carbene intermediate

图式9. Pd-6催化的马来酸二甲酯至富马酸二甲酯的异构

Scheme 9. Pd-6 catalyzed isomerization of dimethyl maleate to dimethyl fumarate

图式10. 经由双核加成消除机理进行的烯烃顺反异构反应

Scheme 10. E/Z Isomerization of alkene via bimetallic addition- elimination mechanism

图式11. 经由亲核钯化反应机理的烯烃异构反应

Scheme 11. E/Z Isomerization of alkene via nucleopalladation pathway

图式12. Pd(MeCN)2Cl2催化的烯烃顺反异构反应

Scheme 12. Pd(MeCN)2Cl2 catalyzed E/Z isomerization of alkene

图式13. (MeCN)2PdCl2催化的烯烃顺反异构反应 (MeCN)2PdCl2催化的烯烃顺反异构反应

Scheme 13. (MeCN)2PdCl2 catalyzed E/Z isomerization of alkene

图式14. Pd(OAc)2/nBu3SnH催化的烯烃顺反异构反应

Scheme 14. Pd(OAc)2/nBu3SnH catalyzed E/Z isomerization of alkene

图15. Pd(dba)2/iPrCOCl体系催化的烯烃顺反异构反应

Scheme 15. Pd(dba)2/iPrCOCl catalyzed E/Z isomerization of alkene

图式16. Pd(PPh3)2Cl2/(EtO)3SiH催化的烯烃顺反异构反应

Scheme 16. Pd(PPh3)2Cl2/(EtO)3SiH catalyzed E/Z isomerization of alkene

图式17. (allyl)Pd(PPh3)Cl催化的烯烃顺反异构反应

Scheme 17. (allyl)Pd(PPh3)Cl catalyzed E/Z isomerization of alkene

图式18. Pd-17催化的烯烃位置异构反应

Scheme 18. Pd-17 catalyzed alkene migratory isomerization

图式19. PdCl2/Et3SiH催化的烯烃位置异构反应

Scheme 19. PdCl2/Et3SiH catalyzed alkene migratory isomerization

图式20. Pd(acac)2/BF3•Et2O催化的烯烃位置异构反应

Scheme 20. Pd(acac)2/BF3•Et2O catalyzed alkene migratory isomerization Pd(acac)2/BF3•Et2O catalyzed alkene migratory isomerization

图式21. Pd(OAc)2催化的烯烃位置异构反应

Scheme 21. Pd(OAc)2 catalyzed alkene migratory isomerization

图式22. Pd/C-H2催化的烯烃位置异构反应

Scheme 22. Pd/C-H2 catalyzed alkene migratory isomerization

图式23. PdCl2催化的烯烃位置异构反应

Scheme 23. PdCl2 catalyzed alkene migratory isomerization

图式24. PdCl2/TaCl5催化的烯烃位置异构反应 PdCl2/TaCl5催化的烯烃位置异构反应

Scheme 24. PdCl2/TaCl5 catalyzed alkene migratory isomerization

图式25. Pd-19催化的烯烃位置异构反应

Scheme 25. Pd-19 catalyzed alkene migratory isomerization

图式26. Pd-21催化的烯烃位置异构反应

Scheme 26. Pd-21 catalyzed alkene migratory isomerization

图式27. Pd-22/NaBArF4催化的烯烃位置异构反应 /NaBArF4催化的烯烃位置异构反应

Scheme 27. Pd-22/NaBArF4 catalyzed alkene migratory isomerization /NaBArF4 catalyzed alkene migratory isomerization

图式28. Pd-24/NaBAr4催化的烯烃位置异构反应

Scheme 28. Pd-24/NaBArF4 catalyzed alkene migratory isomerization

图式29. Pd-25/NaBArF4催化的烯烃异构化反应

Scheme 29. Pd-25/NaBArF4 catalyzed alkene migratory isomerization

图式30. Pd-26, Pd-27和Pd-28催化的烯烃位置异构反应

Scheme 30. Pd-26, Pd-27 and Pd-28 catalyzed alkene migratory isomerization

图式31. [(allyl)PdCl]2催化的烯烃位置异构反应

Scheme 31. [(allyl)PdCl]2 catalyzed alkene migratory isomerization

图式32. [(allyl)PdCl]2体系钯氢产生机制

Scheme 32. Generation of Pd-H intermediate from [(allyl)PdCl]2

图式33. Pd(dba)2/iPrCOCl催化的烯烃位置异构反应

Scheme 33. Pd(dba)2/iPrCOCl catalyzed alkene migratory isomerization

图式34. Pd-30催化的烯烃位置异构反应

Scheme 34. Pd-30 catalyzed alkene migratory isomerization

图式35. Pd(PPh3)2Cl2/(EtO)3SiH催化的烯烃位置异构反应

Scheme 35. Pd(PPh3)2Cl2/(EtO)3SiH catalyzed alkene migratory isomerization

图式36. LnPdCl2/AgOTf/(EtO)2MeSiH催化的烯烃位置异构反应

Scheme 36. LnPdCl2/AgOTf/(EtO)2MeSiH catalyzed alkene migratory isomerization

图式37. Pd(OAc)2/PCy3/B2Pin2催化的烯烃位置异构反应

Scheme 37. Pd(OAc)2/PCy3/B2Pin2 catalyzed alkene migratory isomerization

图式38. Pd(TFA)2/2-PyPPh2/FCH2CH2OH催化的烯烃位置异构反应

Scheme 38. Pd(TFA)2/2-PyPPh2/FCH2CH2OH catalyzed alkene migratory isomerization

图式39. Pd(PtBu3)2催化的β-硼酸酯基烯基硅化合物位置异构反应

Scheme 39. Pd-catalyzed migratory isomerization of β-boryl- alkenylsilanes

图式40. 四氢异喹啉醇64的合成路线

Scheme 40. Synthetic route to tetrahydroisoquinolinol 64

图式41. Andirolide N (70) 的合成路线

Scheme 41. Synthetic route to Andirolide N (70)

图式42. MSVIII-19 (76)的合成路线

Scheme 42. Synthetic routes to MSVIII-19 (76)

图式43. Dihydroisocoumarin (82)的合成路线

Scheme 43. Synthetic routes to dihydroisocoumarin (82)

图式44. Tesirine (86)的全合成

Scheme 44. Total synthesis of tesirine (86)

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钯催化的烯烃异构化反应

Pd-Catalyzed Isomerization of Alkenes

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