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DOI: https://doi.org/10.6023/cjoc202604054

研究论文

磁驱动炔烃的氢三氟甲基化反应

  • 刘浩东 ,
  • 张兆鹏 ,
  • 陈奕龙 ,
  • 赵增典 ,
  • 李新进
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  • 山东理工大学化学化工学院 淄博 255000

收稿日期: 2026-04-30

  修回日期: 2026-07-10

  网络出版日期: 2026-07-24

基金资助

国家自然科学基金(No. 22101157)、先进氟氮材料全国重点实验室开放基金(No. 2026PT0002)资助项目.

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Magnetic field-driven hydrotrifluoromethylation of alkynes

  • Liu Haodong ,
  • Zhang Zhaopeng ,
  • Chen Yilong ,
  • Zhao Zengdian ,
  • Li Xinjin
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  • 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).

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摘要

发展了一种三氟甲基烯烃的绿色合成方法。本方法利用旋转磁场与金属导体, 通过电磁感应使金属棒极化, 实现三氟甲基噻嗯硫盐的单电子还原. 通过调控磁场强度和旋转频率等因素, 以水为氢源, 实现了温和条件下炔烃的氢三氟甲基化反应. 本方法无需使用催化剂及额外添加剂, 且具有很广的底物适应性和官能团兼容性, 为高效构建三氟甲基烯烃化合物提供了新策略。

关键词： 三氟甲基; 氢三氟甲基化; 炔烃; 自由基加成; 磁氧化还原

本文引用格式

刘浩东 , 张兆鹏 , 陈奕龙 , 赵增典 , 李新进 . 磁驱动炔烃的氢三氟甲基化反应[J]. 有机化学, 0 : 202604054 . DOI: 10.6023/cjoc202604054

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.

Key words： Trifluoromethyl; Hydrotrifluoromethylation; Alkynes; Radical addition; Magnetoredox

参考文献

[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.
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