有机膦氧化还原催化反应研究进展

doi:10.6023/cjoc202106004

摘要/Abstract

有机膦试剂在有机合成中占据非常重要的地位, 有机膦化合物介导的Wittig反应、Staudinger反应、Appel反应、Mitsunobu反应发展至今在科学研究和工业生产等方面意义重大. 近年来关于P(III)/P(V)氧化还原循环体系、催化剂的设计, 实现这些反应的催化模式, 避免计量R₃P=O副产物的产生的研究快速发展. 本综述从各个反应出发, 依次介绍这些反应的催化过程的研究进展, 对涉及计量R₃P=O副产物的反应未来可能的发展方向进行了展望.

关键词: Wittig反应, Staudinger反应, Appel反应, Mitsunobu反应, 膦催化, P(III)/P(V)氧化还原催化

Organophosphorus reagents play very important role in organic synthesis. The development of Wittig reaction, Staudinger reaction, Appel reaction and Mitsunobu reaction mediated by phosphine compounds is of great significance in scientific research and industrial production. In recent decades, the research on the design of P(III)/P(V) redox catalysis and catalysts to realize the catalytic mode of these reactions, and avoiding the production of stoichiometric R₃P=O has developed rapidly. This review introduces the research progress of the catalytic process of each reaction in turn. The future research direction in this field about the reactions involving stoichiometric R₃P=O is prospected.

Key words: Wittig reaction, Staudinger reaction, Appel reaction, Mitsunobu reaction, phosphine catalysis, P(III)/P(V) redox catalysis

引用此文

蔡卫, 黄有. 有机膦氧化还原催化反应研究进展[J]. 有机化学, 2021, 41(10): 3903-3913.

Wei Cai, You Huang. Advances in Organophosphorus Redox Catalysis[J]. Chinese Journal of Organic Chemistry, 2021, 41(10): 3903-3913.

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图/表 32

图式1. 计量膦介导的人名反应

Scheme 1. Stoichiometric phosphine mediated name reactions

图式2. 稳定的叶立德参与的催化Wittig反应

Scheme 2. Catalytic Wittig reaction with stabilized ylides

图式3. 室温下的催化Wittig反应

Scheme 3. Catalytic Wittig reaction in room temperature

图式4. 非稳定的叶立德参与的催化Wittig反应

Scheme 4. Catalytic Wittig reaction with unstabilized ylides

图式5. 串联Wittig反应/催化还原反应

Scheme 5. A tandem Wittig/conjugate-reduction reaction.

图式6. 高张力催化剂前体参与的催化Wittig反应

Scheme 6. Catalytic Wittig reaction with high tension precatalyst

图式7. 双膦催化剂参与的催化Wittig反应

Scheme 7. Catalytic Wittig reaction with bisphosphine catalyst

图式8. 其他类型的叶立德前体及催化Wittig反应模式

Scheme 8. Other ylide precursors and catalytic Wittig reaction modes

图式9. 不对称催化Wittig反应

Scheme 9. Asymmetric catalytic Wittig reaction

图式10. 催化Staudinger反应

Scheme 10. Catalytic Staudinger reaction

图式11. PPh3介导的催化Staudinger反应

Scheme 11. PPh3-mediated catalytic Staudinger reaction

图式12. 催化Staudinger酰胺化反应

Scheme 12. Catalytic Staudinger amidation reaction

图式13. 催化Staudinger-氮杂Wittig反应

Scheme 13. Catalytic Staudinger-Aza-Wittig reaction

图式14. PPh3介导的催化Staudinger-氮杂Wittig反应

Scheme 14. PPh3-mediated catalytic Staudinger-Aza-Wittig rea- ction

图式15. 一锅法催化Staudinger-氮杂Wittig反应

Scheme 15. One-pot catalytic Staudinger-Aza-Wittig reaction

图式16. 重氮化合物的催化氮杂Wittig反应

Scheme 16. Catalytic aza-Wittig reaction of diazonium compounds

图式17. 催化不对称氮杂Wittig反应

Scheme 17. Catalytic enantioselective aza-Wittig reaction

图式18. 催化Appel溴化反应

Scheme 18. Catalytic Appel bromination reaction

图式19. 催化Appel氯代反应

Scheme 19. Catalytic Appel chlorination reaction

图式20. 催化Appel酰胺化反应

Scheme 20. Catalytic Appel amidation reaction

图式21. 膦介导的串联催化环化反应

Scheme 21. Phosphetane-mediated tandem annulation reaction

图式22. 催化Mitsunobu反应

Scheme 22. Catalytic Mitsunobu reaction

图式23. 膦氧化物和偶氮二甲酸二酯双催化循环

Scheme 23. Recycling both phosphine oxide and the azocarboxylate reagent

图式24. 氧化还原中性的催化Mitsunobu反应

Scheme 24. Redox-neutral catalytic Mitsunobu reaction

图式25. 催化还原氧原子迁移

Scheme 25. Catalytic reductive O-atom transfer

图式26. 膦介导的催化脱氧缩合反应

Scheme 26. Phosphetane-mediated catalytic deoxygenative condensation reaction

图式27. 膦介导的Cadogen杂环化反应

Scheme 27. Phosphetane-mediated Cadogan heterocyclization reaction

图式28. 膦介导的C—H胺化环化反应

Scheme 28. Phosphetane-mediated C—H amination/cyclization reaction

图式29. 膦介导的C—N还原偶联

Scheme 29. Phosphetane-mediated reductive C—N cross-coupling

图式30. 膦介导的串联反应

Scheme 30. Phosphetane-mediated tandem reaction

图式31. 膦介导的还原巯基化反应

Scheme 31. Phosphine-mediated reductive sulfhydrylation

图式32. 膦介导的氢化还原反应

Scheme 32. Phosphine-mediated hydrogenation reduction

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