氧杂环丁烷的扩环反应

doi:10.6023/cjoc202008046

摘要/Abstract

氧杂环丁烷是一类重要的小杂环化合物, 也是重要有机合成中间体, 在有机化学、药物化学和高分子化学中都有广泛的应用. 作为具有较大环张力的小杂环化合物, 氧杂环丁烷类化合物除可以发生开环反应外, 也很容易发生扩环反应, 构建含氧普通环到大环化合物. 主要总结了氧杂环丁烷的扩环反应, 包括重氮化合物作为卡宾前体与氧杂环丁烷的扩环反应、金属催化的分子间环加成和邻基参与的分子内环加成反应及亲核扩环反应等. 分析了一些扩环反应的机理, 并对扩环反应未来的发展提出了新的展望.

关键词: 氧杂环丁烷, 扩环, 卡宾, 环加成, 亲核反应

Oxetanes are a class of important small heterocycles and intermediates in organic synthesis and have been widely applied in organic, pharmaceutical and polymer chemistries. As small heterocycles with a large ring tension, oxetanes not only prefer ring-opening reactions, but also favor ring expansions, to construct oxygen-containing common to large heterocyclic compounds. The ring expansion reactions of oxetanes, including the ring expansions with diazo compounds as carbene precursors, the metal catalyzed intermolecular cycloadditions and the intramolecular cycloadditions involving neighboring group participation, the nucleophilic ring expansion and so on are reviewed. Some reaction mechanisms of ring expansion reactions are analyzed, and new prospects for the future development of the ring expansion reactions are put forward.

Key words: oxetane, ring expansion, carbene, cycloaddition, nucleophilic reaction

引用此文

袁文豪, 许家喜. 氧杂环丁烷的扩环反应[J]. 有机化学, 2021, 41(3): 947-958.

Wenhao Yuan, Jiaxi Xu. Ring Expansions of Oxetanes[J]. Chinese Journal of Organic Chemistry, 2021, 41(3): 947-958.

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图/表 35

图式1. 2-苯基氧杂环丁烷和重氮乙酸甲酯的反应

Scheme 1. Reaction of 2-phenyloxetane with methyl diazoacetate

图式2. CuOTf和手性联吡啶催化的氧杂环丁烷的扩环反应

Scheme 2. Ring expansion of oxetanes catalyzed by CuOTf and chiral bipyridyl

图式3. CuOTf和双(氮杂二茂铁)催化的氧杂环丁烷的扩环反应

Scheme 3. Ring expansion of oxetanes catalyzed by CuOTf and bisazaferrocene

图式4. Cu(tfacac)2催化的氧杂环丁烷的扩环反应

Scheme 4. Ring expansion of oxetane catalyzed by Cu(tfacac)2

图式5. 光催化的氧杂环丁烷的扩环反应

Scheme 5. Photocatalytic ring expansion reaction of oxetanes

图式6. 光催化扩环反应的反应机理

Scheme 6. Reaction mechanism of the photocatalytic ring expansion of oxetane

图式7. Ru催化的重氮酮酯与氧杂环丁烷的反应

Scheme 7. Ru-catalyzed reaction of diazoketoesters with oxetanes

图式8. Ru催化扩环反应的反应机理

Scheme 8. Reaction mechanism of Ru-catalyzed ring expansion reaction

图式9. 重氮酮酯与氧杂环丁烷的反应

Scheme 9. Reaction of α-diazo-β-oxoalkanoates with oxetanes

图式10. 重氮萘醌与氧杂环丁烷的反应

Scheme 10. Reaction of diazonaphthoquinones with oxetane

图式11. 由磺酰基三唑转化为金属卡宾

Scheme 11. Formation of metallocarbenes from N-sulfonyl- triazoles

图式12. 低浓度下磺酰基三唑与氧杂环丁烷的反应

Scheme 12. Reaction of sulfonyltriazoles with 3,3-dimethyl- oxetane at low concentration

图式13. 高浓度下磺酰基三唑与氧杂环丁烷的反应

Scheme 13. Reaction of sulfonyltriazoles with 3,3-dimethyl- oxetane at high concentration

图式14. 甲磺酰基三唑与3,3-二甲基氧杂环丁烷的反应

Scheme 14. Reaction of methanesulfonyl triazoles with 3,3- dimethyloxetane

图式15. 磺酰基三唑与氧杂环丁烷反应的反应机理

Scheme 15. Reaction mechanism of sulfonyltriazoles with oxetane

图式16. 乙烯基氧杂环丁烷和碳二酰亚胺或异氰酸酯的反应

Scheme 16. Reactions of vinyloxetanes with carbodiimides and isocyanates

图式17. 烯醇硅醚与氧杂环丁烷的反应

Scheme 17. Reaction of silyl enol ethers with oxetane

图式18. N-炔基酰胺与氧杂环丁烷的反应

Scheme 18. Reaction of N-alkynylamides with oxetanes

图式19. 丙炔酸叔丁酯与氧杂环丁烷的反应

Scheme 19. Reaction of tert-butyl propiolates with oxetanes

图式20. 氮杂二烯和乙烯基氧杂环丁烷的反应

Scheme 20. Reaction of azadienes with vinyloxetanes

图式21. 甲醛和2-乙烯基氧杂环丁烷的反应

Scheme 21. Reaction of formaldehyde with 2-vinyloxetanes

图式22. 苯并噁嗪酮和乙烯基氧杂环丁烷的反应

Scheme 22. Reaction of benzoxazinones with vinyloxetanes

图式23. Cu催化的乙烯基氧杂环丁烷分子内扩环反应

Scheme 23. Cu-catalyzed intramolecular ring expansion of vinyloxetanes

图式24. Cu(I)催化炔基氧杂环丁烷扩环合成二氢呋喃-2-甲醛和六元环内酯

Scheme 24. Cu(I)-catalyzed ring expansions of 2-ethynyl- oxetane to dihydrofuran-2-carbaldehydes and six-membered lactones

图式25. 氧杂环丁烷和CO2或异氰酸酯的反应

Scheme 25. Reactions of oxetane with CO2 and isocyanates

图式26. 氧杂环丁烷和烯酮的反应

Scheme 26. Reactions of oxetane with ketene

图式27. Cr-Salen配合物催化的氧杂环丁烷与CO2的反应

Scheme 27. Cr-Salen complex-catalyzed reaction of oxetane and CO2

图式28. VO(acac)2催化的氧杂环丁烷与CO2的反应

Scheme 28. Reaction of oxetane and CO2 catalyzed by VO(acac)2

图式29. 氨基三酚铁络合物催化的氧杂环丁烷与CO2的反应

Scheme 29. Iron amino triphenolate complex-catalyzed reaction of oxetane and CO2

图式30. 氨基三酚铝络合物催化的氧杂环丁烷与CO2的反应

Scheme 30. Reaction of oxetane and CO2 catalyzed by aluminum amino triphenolate complex

图式31. 氨基三酚铝络合物催化的多取代氧杂环丁烷与CO2的反应

Scheme 31. Reaction of polysubstituted oxetane and CO2 catalyzed by aluminum amino triphenolate complex

图式32. 电催化的氧杂环丁烷与CO2的反应

Scheme 32. Electrocatalytic reaction of oxetane and CO2

图式33. 氧杂环丁烷与CO2的反应

Scheme 33. Reaction of oxetane and CO2

图式34. 硫叶立德和氧杂环丁烷的扩环反应

Scheme 34. Ring expansion reaction of sulfur ylide and oxetanes

图式35. 苯甲酰胺与氧杂环丁烷的扩环反应

Scheme 35. Ring expansion reaction of benzamides and oxetanes

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