Pd-Catalyzed Isomerization of Alkenes

doi:10.6023/cjoc202109045

Chinese Journal of Organic Chemistry ›› 2022, Vol. 42 ›› Issue (3): 742-757.DOI: 10.6023/cjoc202109045 Previous Articles Next Articles

REVIEWS

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)

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

Cite this article

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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Fig. & Tab. 44

Scheme 1. Application and transformation of alkenes

Scheme 2. Main processes for Pd-catalyzed alkene isomerization

Scheme 3. Production pathway for vinyl chloride formation

Scheme 4. Experimental studies on carbocation intermediate mechanism

Scheme 5. Alkene isomerization via allyl-Pd intermediate

Scheme 6. PdCl2/FeCl3 catalyzed alkene migratory isomerization

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

Scheme 8. Migratory isomerization of alkene via palladium carbene intermediate

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

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

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

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

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

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

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

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

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

Scheme 18. Pd-17 catalyzed alkene migratory isomerization

Scheme 19. PdCl2/Et3SiH catalyzed alkene migratory isomerization

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

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

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

Scheme 23. PdCl2 catalyzed alkene migratory isomerization

Scheme 24. PdCl2/TaCl5 catalyzed alkene migratory isomerization

Scheme 25. Pd-19 catalyzed alkene migratory isomerization

Scheme 26. Pd-21 catalyzed alkene migratory isomerization

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

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

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

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

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

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

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

Scheme 34. Pd-30 catalyzed alkene migratory isomerization

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

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

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

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

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

Scheme 40. Synthetic route to tetrahydroisoquinolinol 64

Scheme 41. Synthetic route to Andirolide N (70)

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

Scheme 43. Synthetic routes to dihydroisocoumarin (82)

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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