Zweifel烯化反应:迈向高效立体选择性合成烯烃的创新之路

黄熠 肖岩松 马星星 宋秋玲

引用本文: 黄熠, 肖岩松, 马星星, 宋秋玲. Zweifel烯化反应:迈向高效立体选择性合成烯烃的创新之路[J]. 大学化学, 2026, 41(7): 119-125. doi: 10.12461/PKU.DXHX202506046 shu
Citation:  Yi Huang,  Yansong Xiao,  Xingxing Ma,  Qiuling Song. Zweifel olefination: an innovative approach to highly efficient stereoselective alkene synthesis[J]. University Chemistry, 2026, 41(7): 119-125. doi: 10.12461/PKU.DXHX202506046 shu

Zweifel烯化反应:迈向高效立体选择性合成烯烃的创新之路

    通讯作者: 马星星,Email:maxx@fzu.edu.cn; 宋秋玲,Email:qsong@fzu.edu.cn
  • 基金项目:

    污染物分析与资源化技术湖北省重点实验室开放基金重点项目(PA240102)

    福建省自然科学基金(2022J02009)

摘要: Zweifel烯化反应是构建C=C双键的有效方法,具有高效、高立体选择性且无需过渡金属催化剂等显著优势。本文总结了该反应的机理、反应历程及其最新研究进展。通过系统阐述这一新颖的烯烃立体合成策略,旨在帮助大学化学专业学生深化对立体化学的理解,拓展获取单一构型烯烃的思路,从而促进其有机合成知识体系的丰富与完善。

English

    1. [1]

      F. He, Y. Huang, L. Jiang, W.H. Liu, Org. Lett. 2025, 27, 2587.F. He, Y. Huang, L. Jiang, W.H. Liu, Org. Lett. 2025, 27, 2587.

    2. [2]

      K. Kobayashi, K. Tanaka, III, H. Kogen, Tetrahedron Lett. 2018, 59, 568.K. Kobayashi, K. Tanaka, III, H. Kogen, Tetrahedron Lett. 2018, 59, 568.

    3. [3]

      A.M. Borys, E.F. Rice, G.S. Nichol, M.J. Cowley, J. Am. Chem. Soc. 2021, 143, 14065.A.M. Borys, E.F. Rice, G.S. Nichol, M.J. Cowley, J. Am. Chem. Soc. 2021, 143, 14065.

    4. [4]

      V. Varsha, S. Radhika, G. Anilkumar, Curr. Org. Synth. 2024, 21, 97.V. Varsha, S. Radhika, G. Anilkumar, Curr. Org. Synth. 2024, 21, 97.

    5. [5]

      J.Q. Xie, R.X. Liang, Y.X. Jia, Chin. J. Chem. 2021, 39, 710.J.Q. Xie, R.X. Liang, Y.X. Jia, Chin. J. Chem. 2021, 39, 710.

    6. [6]

      L.F. van Staden, D. Gravestock, D.J. Ager, Chem. Soc. Rev. 2002, 31, 195.L.F. van Staden, D. Gravestock, D.J. Ager, Chem. Soc. Rev. 2002, 31, 195.

    7. [7]

      C.C. McAtee, P.S. Riehl, C.S. Schindler, J. Am. Chem. Soc. 2017, 139, 2960.C.C. McAtee, P.S. Riehl, C.S. Schindler, J. Am. Chem. Soc. 2017, 139, 2960.

    8. [8]

      K. Wu, N. Sun, B. Hu, Z. Shen, L. Jin, X. Hu, Adv. Synth. Catal. 2018, 360, 3038.K. Wu, N. Sun, B. Hu, Z. Shen, L. Jin, X. Hu, Adv. Synth. Catal. 2018, 360, 3038.

    9. [9]

      邢其毅, 裴伟伟, 徐瑞秋, 裴坚. 基础有机化学(下册). 第4版. 北京: 北京大学出版社, 2016: 1157–1195.

    10. [10]

      R.J. Armstrong, V.K. Aggarwal, Synthesis 2017, 49, 3323.R.J. Armstrong, V.K. Aggarwal, Synthesis 2017, 49, 3323.

    11. [11]

      G. Zweifel, H. Arzoumanian, C.C. Whitney, J. Am. Chem. Soc. 1967, 89, 3652.G. Zweifel, H. Arzoumanian, C.C. Whitney, J. Am. Chem. Soc. 1967, 89, 3652.

    12. [12]

      G. Zweifel, R.P. Fisher, J.T. Snow, C.C. Whitney, J. Am. Chem. Soc. 1972, 94, 6560.G. Zweifel, R.P. Fisher, J.T. Snow, C.C. Whitney, J. Am. Chem. Soc. 1972, 94, 6560.

    13. [13]

      G. Zweifel, N.L. Polston, C.C. Whitney, J. Am. Chem. Soc. 1968, 90, 6243.G. Zweifel, N.L. Polston, C.C. Whitney, J. Am. Chem. Soc. 1968, 90, 6243.

    14. [14]

      H.C. Brown, D. Basavaiah, S.U. Kulkarni, N.G. Bhat, J.V. Prasad, J. Org. Chem. 1988, 53, 239.H.C. Brown, D. Basavaiah, S.U. Kulkarni, N.G. Bhat, J.V. Prasad, J. Org. Chem. 1988, 53, 239.

    15. [15]

      (a) D.A. Evans, R.C. Thomas, J.A. Walker, Tetrahedron Lett. 1976, 17, 1427. (b) D.A. Evans, T.C. Crawford, R.C. Thomas, J.A, Walker. J. Org. Chem. 1976, 41, 3947.(a) D.A. Evans, R.C. Thomas, J.A. Walker, Tetrahedron Lett. 1976, 17, 1427. (b) D.A. Evans, T.C. Crawford, R.C. Thomas, J.A, Walker. J. Org. Chem. 1976, 41, 3947.

    16. [16]

      D.S. Matteson, P.K. Jesthi, J. Organomet. Chem. 1976, 110, 25D.S. Matteson, P.K. Jesthi, J. Organomet. Chem. 1976, 110, 25

    17. [17]

      R.J. Armstrong, W. Niwetmarin, V.K. Aggarwal, Org. Lett. 2017, 19, 2762.R.J. Armstrong, W. Niwetmarin, V.K. Aggarwal, Org. Lett. 2017, 19, 2762.

    18. [18]

      A. Music, C. Hoarau, N. Hilgert, F. Zischka, D. Didier, Angew. Chem. Int. Ed. 2019, 58, 1188.A. Music, C. Hoarau, N. Hilgert, F. Zischka, D. Didier, Angew. Chem. Int. Ed. 2019, 58, 1188.

    19. [19]

      A. Suzuki, N. Miyaura, S. Abiko, M. Itoh, H.C. Brown, J.A. Sinclair, M.M. Midland, J. Am. Chem. Soc. 1973, 95, 3080.A. Suzuki, N. Miyaura, S. Abiko, M. Itoh, H.C. Brown, J.A. Sinclair, M.M. Midland, J. Am. Chem. Soc. 1973, 95, 3080.

    20. [20]

      M. Ye, M. Hou, Y. Wang, X. Ma, K. Yang, Q. Song, Org. Lett. 2023, 25, 1787.M. Ye, M. Hou, Y. Wang, X. Ma, K. Yang, Q. Song, Org. Lett. 2023, 25, 1787.

    21. [21]

      G. Zhang, B. Feng, Y. Wang, J. Chen, X. Ma, Q. Song, Org. Lett. 2024, 26, 3109.G. Zhang, B. Feng, Y. Wang, J. Chen, X. Ma, Q. Song, Org. Lett. 2024, 26, 3109.

    22. [22]

      X. Ma, L. Li, M. Tan, Z. Zhong, J. Liang, P. Li, Q. Song, Chem 2023, 9, 1164.X. Ma, L. Li, M. Tan, Z. Zhong, J. Liang, P. Li, Q. Song, Chem 2023, 9, 1164.

    23. [23]

      A.N. Baumann, A. Music, J. Dechent, N. Meller, T.C. Jagau, D. Didier, Chem. Eur. J. 2020, 26, 8382.A.N. Baumann, A. Music, J. Dechent, N. Meller, T.C. Jagau, D. Didier, Chem. Eur. J. 2020, 26, 8382.

    24. [24]

      A. Music, A.N. Baumann, F. Boser, N. Müller, F. Matz, T.C. Jagau, D. Didier, Chem. Eur. J. 2021, 27, 4322.A. Music, A.N. Baumann, F. Boser, N. Müller, F. Matz, T.C. Jagau, D. Didier, Chem. Eur. J. 2021, 27, 4322.

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  • 发布日期:  2025-10-30
  • 收稿日期:  2025-06-10
  • 修回日期:  2025-09-02
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