Zweifel烯化反应：迈向高效立体选择性合成烯烃的创新之路

doi:10.12461/PKU.DXHX202506046

Abstract

Abstract: The Zweifel olefination serves as an effective methodology for constructing C=C double bonds, distinguished by its high efficiency, exceptional stereoselectivity, and transition-metal-free catalytic system. This review comprehensively examines the reaction mechanism, pathway, and recent advancements in this field. Through a systematic discussion of this novel stereoselective alkene synthesis strategy, we intend to enhance undergraduate chemistry students’ understanding of stereochemical principles while expanding their repertoire for obtaining alkenes with defined configurations. This perspective ultimately contributes to the enrichment of their organic synthesis knowledge framework.

Key words: Zweifel reaction, C=C double bond, High stereoselectivity, Transition-metal-free catalyst

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.

References

[1] F. He, Y. Huang, L. Jiang, W.H. Liu, Org. Lett. 2025, 27, 2587.
[2] K. Kobayashi, K. Tanaka, III, H. Kogen, Tetrahedron Lett. 2018, 59, 568.
[3] A.M. Borys, E.F. Rice, G.S. Nichol, M.J. Cowley, J. Am. Chem. Soc. 2021, 143, 14065.
[4] V. Varsha, S. Radhika, G. Anilkumar, Curr. Org. Synth. 2024, 21, 97.
[5] J.Q. Xie, R.X. Liang, Y.X. Jia, Chin. J. Chem. 2021, 39, 710.
[6] L.F. van Staden, D. Gravestock, D.J. Ager, Chem. Soc. Rev. 2002, 31, 195.
[7] C.C. McAtee, P.S. Riehl, C.S. Schindler, J. Am. Chem. Soc. 2017, 139, 2960.
[8] K. Wu, N. Sun, B. Hu, Z. Shen, L. Jin, X. Hu, Adv. Synth. Catal. 2018, 360, 3038.
[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] R.J. Armstrong, V.K. Aggarwal, Synthesis 2017, 49, 3323.
[11] G. Zweifel, H. Arzoumanian, C.C. Whitney, J. Am. Chem. Soc. 1967, 89, 3652.
[12] G. Zweifel, R.P. Fisher, J.T. Snow, C.C. Whitney, J. Am. Chem. Soc. 1972, 94, 6560.
[13] G. Zweifel, N.L. Polston, C.C. Whitney, J. Am. Chem. Soc. 1968, 90, 6243.
[14] H.C. Brown, D. Basavaiah, S.U. Kulkarni, N.G. Bhat, J.V. Prasad, J. Org. Chem. 1988, 53, 239.
[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.
[16] D.S. Matteson, P.K. Jesthi, J. Organomet. Chem. 1976, 110, 25
[17] R.J. Armstrong, W. Niwetmarin, V.K. Aggarwal, Org. Lett. 2017, 19, 2762.
[18] A. Music, C. Hoarau, N. Hilgert, F. Zischka, D. Didier, Angew. Chem. Int. Ed. 2019, 58, 1188.
[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.
[20] M. Ye, M. Hou, Y. Wang, X. Ma, K. Yang, Q. Song, Org. Lett. 2023, 25, 1787.
[21] G. Zhang, B. Feng, Y. Wang, J. Chen, X. Ma, Q. Song, Org. Lett. 2024, 26, 3109.
[22] X. Ma, L. Li, M. Tan, Z. Zhong, J. Liang, P. Li, Q. Song, Chem 2023, 9, 1164.
[23] A.N. Baumann, A. Music, J. Dechent, N. Meller, T.C. Jagau, D. Didier, Chem. Eur. J. 2020, 26, 8382.
[24] A. Music, A.N. Baumann, F. Boser, N. Müller, F. Matz, T.C. Jagau, D. Didier, Chem. Eur. J. 2021, 27, 4322.

Zweifel olefination: an innovative approach to highly efficient stereoselective alkene synthesis

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