碳-杂原子键复分解反应的研究进展

doi:10.6023/cjoc202202003

摘要/Abstract

复分解反应作为一种重要的化学键重组反应, 被认为是构建常规路径无法获得的复杂分子的重要方法, 极大地推动了合成化学的发展. 然而, 目前已知的复分解反应大多局限于多重键的重组反应, 碳-杂原子键的复分解反应由于其键能比较高, 不容易被切断, 面临着诸多机遇和挑战. 根据成键类型进行划分, 总结了近十年来过渡金属及氢键催化的C—Si、C—P、C—S、C—I、C—O和C—N键复分解反应的研究进展.

关键词: 化学键重组, 碳-杂原子键复分解, 杂环化合物

Metathesis reaction, as a new type of chemical bond reorganization reaction, proved remarkably powerful for constructing inaccessible complex molecules by other methods in both industrial and academic settings, which greatly promotes the development of synthetic chemistry. However, most of the known metathesis reactions are mainly limited to the recombination reaction of multiple bonds, and the metathesis reactions of C—X single bonds are still in their infancy and face many opportunities and challenges. This is mainly due to the high bond energy of the C—X bonds, which is hard to break and reorganize. The progress of C—Si, C—P, C—S, C—I, C—O and C—N bonds metathesis reactions and their applications in organic synthesis are summarized according to the type of bonding.

Key words: chemical bond reorganization, C—X bond metathesis, heterocyclic compounds

引用此文

于帮魁, 黄汉民. 碳-杂原子键复分解反应的研究进展[J]. 有机化学, 2022, 42(8): 2376-2389.

Bangkui Yu, Hanmin Huang. Recent Advances in C—X Bond Metathesis Reactions[J]. Chinese Journal of Organic Chemistry, 2022, 42(8): 2376-2389.

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图/表 33

图式1. C—X键复分解的反应类型

Scheme 1. Types of C—X bond metathesis reactions

图式2. 氢硅烷取代基的重新分布

Scheme 2. Substituent redistribution of hydrosilanes

图式3. 氢硅烷的C—Si/Si—H键交叉复分解

Scheme 3. C—Si/Si—H bond cross-metathesis of hydrosilanes

图式4. 氢硅烷交叉复分解的反应机理

Scheme 4. Possible mechanism of cross-metathesis of hydrosilanes

图式5. 环锗和硅烷的C—Si/Si—H键交叉复分解

Scheme 5. C—Si/Si—H bond cross-metathesis of cyclicgermylenes and hydrosilanes

图式6. 镱催化的氢硅烷的C—Si/Si—H键交叉复分解

Scheme 6. Ytterbium-catalyzed C—Si/Si—H bond cross-metathesis of silanes

图式7. 芳基鏻盐的产生及应用

Scheme 7. Generation and application of arylphosphonium salt

图式8. 钯催化的C—P/C—P键复分解反应

Scheme 8. Palladium-catalyzed C—P/C—P bond metathesis reaction

图式9. C—P键复分解反应的机理

Scheme 9. Possible mechanism of C—P bond metathesis reaction

图式10. 钯催化的官能团复分解反应

Scheme 10. Palladium-catalyzed functional group metathesis reaction

图式11. 钯和镍催化C—P键复分解的区别

Scheme 11. Differentiation of C—P bond metathesis catalyzed by Pd and Ni

图式12. 镍催化的C—P键复分解反应

Scheme 12. Nickel-catalyzed C—P bond metathesis reaction

图式13. 控制实验

Scheme 13. Control experiments

图式14. 钯催化的C—S/S—H键复分解反应

Scheme 14. Palladium-catalyzed C—S/S—H bond metathesis reaction

图式15. C—S键复分解的反应机理

Scheme 15. Possible mechanism of C—S bond metathesis reaction

图式16. 镍催化的C—S/S—H键复分解反应

Scheme 16. Nickel-catalyzed C—S/S—H bond metathesis reaction

图式17. 离子液体催化的C—S/C—Br键复分解反应

Scheme 17. IL-catalyzed C—S/C—Br bond metathesis reaction

图式18. 镍催化芳基腈和芳基硫醚的官能团复分解反应

Scheme 18. Nickel-catalyzed functional group metathesis between aryl nitriles and aryl thioethers

图式19. 镍催化芳基硫醚和芳基亲电试剂的官能团复分解反应

Scheme 19. Nickel-catalyzed functional group metathesis between aryl thioethers and aryl electrophilies

图式20. 碘鎓的复分解反应

Scheme 20. Iodonium metathesis reaction

图式21. 铜催化的C—I/C—H键复分解反应

Scheme 21. Copper-catalyzed C—I/C—H bond metathesis reaction

图式22. 钯催化的C—I/C—Cl键复分解反应

Scheme 22. Palladium-catalyzed C—I/C—Cl bond metathesis reaction

图式23. 铁催化的C—O/C—O键关环复分解反应

Scheme 23. Iron-catalyzed C—O/C—O bond ring-closing metathesis reaction

图式24. 离子液体催化的C—O/C—O键关环复分解反应

Scheme 24. IL-catalyzed C—O/C—O bond ring-closing metathesis reaction

图式25. 酰胺键的复分解反应

Scheme 25. Amide bond metathesis

图式26. 镍催化酰胺的C—N/N—H键复分解反应

Scheme 26. Nickel-catalyzed C—N/N—H bond metathesis reaction of amide

图式27. 钯催化的三级胺的胺交换反应

Scheme 27. Palladium-catalyzed amine exchange of tertiary amines

图式28. 胺交换的反应机理

Scheme 28. Possible mechanism of amine exchange

图式29. 钌催化的胺的C—N/N—H键复分解反应

Scheme 29. Ruthenium-catalyzed C—N/N—H bond metathesis of amines

图式30. 钴催化烷基胺的C—N/N—H键复分解反应

Scheme 30. Cobalt-catalyzed C—N/N—H bond metathesis of alkylamines

图式31. C—N键复分解的基元反应

Scheme 31. Elementary reaction of C—N bond metathesis

图式32. 钯催化C—N键复分解的关环反应

Scheme 32. Palladium-catalyzed ring-closing reaction via C—N bond metathesis

图式33. 钯催化C—N键复分解反应的机理

Scheme 33. Possible mechanism of palladium-catalyzed C—N bond metathesis reaction

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