ARTICLE

Magnetic field-driven hydrotrifluoromethylation of alkynes

  • Liu Haodong ,
  • Zhang Zhaopeng ,
  • Chen Yilong ,
  • Zhao Zengdian ,
  • Li Xinjin
Expand
  • School of Chemistry and Chemical Engineering, Shandong University of Technology, Zibo, 255000

Received date: 2026-04-30

  Revised date: 2026-07-10

  Online published: 2026-07-24

Supported by

National Natural Science Foundation of China (No. 22101157) and the State Key Laboratory of Fluorine and Nitrogen Chemistry and Advanced Materials (No. 2026PT0002).

Abstract

A green protocol for the synthesis of trifluoromethylated alkenes has been developed. This method utilizes a rotating magnetic field and metal rods, where electromagnetic induction polarizes the metal rods to enable single-electron reduction of trifluoromethyl thianthrenium salts. Through regulation of magnetic intensity and rotating frequency, the hydrotrifluoromethylation of alkynes is achieved by using H2O as the hydrogen source under mild conditions. This approach requires no catalysts or additional additives, exhibits broad substrate scope and high functional group tolerance, and provides a new strategy for the efficient construction of trifluoromethylated alkenes.

Cite this article

Liu Haodong , Zhang Zhaopeng , Chen Yilong , Zhao Zengdian , Li Xinjin . Magnetic field-driven hydrotrifluoromethylation of alkynes[J]. Chinese Journal of Organic Chemistry, 0 : 202604054 . DOI: 10.6023/cjoc202604054

References

[1] For selected reviews, see:
(a) Yu X.-Y.; Chen J.-R.; Xiao W.-J. Chem. Rev.2021, 121, 506.
(b) Bellotti P.; Huang H.-M.; Faber T.; Glorius F. Chem. Rev.2024, 123, 4237.
(c) Huang T.; Du P.; Lin, Y.-M. Chin. J. Chem.2025, 43, 2566.
[2] For selected examples, see:
(a) Kubota K.; Pang Y.; Miura A.; Ito H. Science2019, 366, 1500.
(b) Schumacher C.; Hernández J. G.; Bolm, C. Angew. Chem., Int. Ed.2020, 59, 16357.
(c) Pang Y.; Lee J. W.; Kubota K.; Ito, H. Angew. Chem., Int. Ed.2020, 59, 22570.
(d) Lv H.; Xu X.; Li J.; Huang X.; Fang G.; Zheng, L. Angew. Chem., Int. Ed.2022, 61, e202206420.
(e) Wang X.; Zhang X.; Xue L.; Wang Q.; You F.; Dai L.; Wu J.; Kramer S.; Lian, Z. Angew. Chem., Int. Ed.2023, 62, e202307054.
(f) Feng Q.; Qin R.; Ma Y.; Wang T.; Zhang S.; Ge D.; Shi L.; Liang D. ACS Catal.2025, 15, 19850.
[3] Liu H.; Han X.; Feng X.; Zhang L.; Sun F.; Jia F.; Zhao Z.; Liu H.; Li, X. J. Am. Chem. Soc.2024, 146, 18143.
[4] (a) Han X.; Liu H.; Feng X.; Jia F.; Zhao Z.; Li, X. Chin. J. Chem.2025, 43, 155
(b) Feng X.; Li X.; Zhang N.; Zhang L.; Sun F.; Liu H.; Li, X. J. Am. Chem. Soc.2025, 147, 12664.
[5] (a) Bégué, J.-P.; Bonnet-Delpon, D. Bioorganic and Medicinal Chemistry of Fluorine, Wiley, Hoboken, 2008, pp. 1-22.
(b) Purser S.; Moore P. R.; Swallow S.; Gouverneur, V. Chem. Soc. Rev.2008, 37, 320.
(c) Qing, F. Chin. J. Org. Chem.2012, 32, 815 (in Chinese).
(卿凤翎, 有机化学, 2012, 32, 815).
(d) Ni, C.; Hu, J.Chem. Soc. Rev. 2016, 45, 5441.
[6] (a) Charpentier J.; Früh N.; Togni A. Chem. Rev.2015, 115, 650.
(b) Ni, C.; Hu, M.; Hu, J.Chem. Rev. 2015, 115, 765.
(c) Chen D.; Yang W.; Yao Y.; Yang X.; Deng Y.; Yang, D. Chin. J. Org. Chem.2018, 38, 2571 (in Chinese).
(陈董涵, 杨文, 姚永祺, 杨新, 邓颖颍, 杨定乔, 有机化学, 2018, 38, 2571).
(d) Xiao H.; Zhang Z.; Fang Y.; Zhu L.; Li, C. Chem. Soc. Rev.2021, 50, 6308.
(e) Zhang L.; Li Y.; Huang D.; Wu, J. Asian J. Org. Chem.2025, 14, e00550.
[7] (a) Choi S.; Kim Y. J.; Kim S. M.; Yang J. W.; Kim S. W.; Cho, E. J. Nat. Commun.2014, 5, 4881.
(b) Gao, P.; Song, X.-R.; Liu, X.-Y.; Liang, Y.-M.Chem. Eur. J. 2015, 21, 7648.
(c) Cheng Y.; Yu S. Org. Lett.2016, 18, 2962.
(d) Jang, J.; Cho, E. J.Chem. Commun. 2025, 61, 11802.
[8] (a) Iqbal N.; Jung J.; Park S.; Cho, E. J. Angew. Chem., Int. Ed.2014, 53, 539.
(b) Ren Y.-Y.; Zheng X.; Zhang X. Synlett2018, 29, 1028.
(c) Shi X.; Song T.; Li Q.; Guo X.; Yang Y. Org. Lett.2022, 24, 8724.
[9] Mizuta S.; Verhoog S.; Engle K. M.; Khotavivattana T.; O’Duill M.; Wheelhouse K.; Rassias G.; Médebielle M.; Gouverneur, V. J. Am. Chem. Soc.2013, 135, 2505
[10] Pitre S. P.; McTiernan C. D.; Ismaili H.; Scaiano, J. C. ACS Catal.2014, 4, 2530.
[11] Jang J.; Cho, E. J. Chem. Commun.2025, 61, 11802.
[12] Jia H.; Häring A. P.; Berger F.; Zhang L.; Ritter, T. J. Am. Chem. Soc.2021, 143, 7623.
[13] Yus, M.; Foubelo, F.; Ferrández, J. V.Tetrahedron 2003, 59, 2083.
[14] Dénès, F., Pichowicz, M., Povie, G.; Renaud P. Chem. Rev.2014, 114, 2587.
[15] Huang Y.; Hayashi, T. J. Am. Chem. Soc.2016, 138, 12340.
[16] Yu, B. Jiang, Z.-X.; Xiao, N.WO 200834095, 2008.
[17] Qiu, R.; Chen, S. Tang, N. Yang. W.; Kobe, N.CN 116836104, 2023.
[18] Yang, X. Tsui, G. C, Org. Lett.2019, 21, 1521.
[19] Zhou W.; Zhao Q.-W.; Luo Y.-C.; Zhang X. Synthesis2023, 55, 1844.
[20] Zhang, X. Qing F.; Yu, Y. J. Org. Chem.2000, 65, 7075.
Outlines

/