Magnetic field-driven hydrotrifluoromethylation of alkynes

doi:10.6023/cjoc202604054

Chinese Journal of Organic Chemistry Previous Articles Next Articles

ARTICLE

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^*

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
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.

Magnetic field-driven hydrotrifluoromethylation of alkynes

Liu Haodong, Zhang Zhaopeng, Chen Yilong, Zhao Zengdian, Li Xinjin^*

School of Chemistry and Chemical Engineering, Shandong University of Technology, Zibo, 255000

Received:2026-04-30 Revised:2026-07-10
Contact: ^*E-mail: lixj@sdut.edu.cn
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).

1. .pdf(3734KB)

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

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, doi: 10.6023/cjoc202604054.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

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.

磁驱动炔烃的氢三氟甲基化反应

Magnetic field-driven hydrotrifluoromethylation of alkynes

PDF

Supporting Info.

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Bin Wang, Bo Ye, Lei Wang, Hong He, Yongmin Ma. Photoinduced C—F Bond Cleavage α-Trifluoromethyl Alkenes for the Synthesis of gem-Difluoroalkenes [J]. Chinese Journal of Organic Chemistry, 2026, 46(8): 3219-3226.
[2]	Liping Chen, Rui Ma, Jianjun Chi, Yufan Jin, Qing Wang, Yang Wang, Xuehua Zhu, Yubo Pang. Cobalt-Catalyzed α-Arylation of 1-Trimethylsilyl-2-aryl Acetylene [J]. Chinese Journal of Organic Chemistry, 2026, 46(7): 2760-2769.
[3]	Mingyue Fu, Zhan Dong, Wei Chen, Tie-Gen Chen. Recent Advances in Deuterium Functionalization Reactions of Alkenes and Alkynes [J]. Chinese Journal of Organic Chemistry, 2026, 46(6): 2207-2226.
[4]	Mei Zhang, Man Chen, Yu Chen, Qiuli Yao, Anjun Wang. Tetrabutylammonium Fluoride-Promoted Hydrothiolation of α-(Trifluoromethyl)styrenes with Thiophenols [J]. Chinese Journal of Organic Chemistry, 2026, 46(6): 2346-2357.
[5]	Fu Ye, Weiming Yuan. Recent Advances in Dicarbofunctionalization of Alkynes via Photoredox Catalysis [J]. Chinese Journal of Organic Chemistry, 2026, 46(4): 1146-1165.
[6]	Dongsheng Li, Haowen Zheng, Hongping Deng. Trifluoromethyl Radical-Mediated C(sp³)—H Alkylation Enabled by Photoinduced Thioxanthone Catalysis [J]. Chinese Journal of Organic Chemistry, 2026, 46(4): 1722-1729.
[7]	Yu Sun, Yantao Zhu, Dong Zhang, Chunjie Ni. Nickel-Catalyzed Annulation of Alkynyl with Trifluoroacetimidoyl Chlorides and H₂O: Facile Access to 2‑(Trifluoromethyl)indole Derivatives [J]. Chinese Journal of Organic Chemistry, 2026, 46(3): 1017-1026.
[8]	Rundong Fan, Bingran Chen, Fuqi Li, Jinxiu Chen, Qiongjiao Yan, Wei Wang, Hui Zhou. Photosensitizer-Free Photoinduced Hydrodifluoroalkylation of α‑Trifluoromethyl Alkenes [J]. Chinese Journal of Organic Chemistry, 2026, 46(2): 641-652.
[9]	Yilin Chen, Jiayi Yue, Yiming Lin, Bingni Liu, Wen Dai, Hongping Zhu. Synthesis and Characterization of Silacyclopropenes [J]. Chinese Journal of Organic Chemistry, 2026, 46(1): 128-134.
[10]	Yinsheng Miao, Lei Zhang, Jianqi Chen, Lili Wang, Zheng Duan. Synthesis of Pyrazolo(iso)quinoline Derivatives from Aryl Alkynes and N-Imine(iso)quinoline Ylides Catalyzed by Bisphosphonium Salt [J]. Chinese Journal of Organic Chemistry, 2025, 45(8): 2876-2884.
[11]	Xiaopei Chen, Qinglong Wang, Xuehui Hou, Chuanchuan Wang, Zhiwei Ma, Jingyu Zhang. Recent Progress on the Application of CF₃-Imidoyl Sulfoxonium Ylides in Annulation Reactions [J]. Chinese Journal of Organic Chemistry, 2025, 45(8): 2796-2814.
[12]	Ting Mao, Linyuan Zeng, Jilin Wen, Jia Jia. Visible Light-Mediated Iridium-Catalyzed Debromocyclization of Aliphatic α-Bromotrifluoromethyl Groups [J]. Chinese Journal of Organic Chemistry, 2025, 45(7): 2520-2528.
[13]	Shuai Liu, Kunquan Chen, Dequn Sun, Qiang Liu, Xiangyu Chen. Intramolecular Charge Transfer Complex Enabled Trifluoromethylation of Heteroarenes with Trifluoromethyl Phosphonium Salt [J]. Chinese Journal of Organic Chemistry, 2025, 45(7): 2545-2551.
[14]	Tianxing Lin, Tianfei Liu. Research Advances in the Synthetic Methodologies of N-Trifluoromethylamides [J]. Chinese Journal of Organic Chemistry, 2025, 45(6): 1995-2006.
[15]	Chenyang Jiang, Yanli Yin, Zhiyong Jiang. Advances in Photoenzyme-Catalyzed Asymmetric Radical Addition Reactions [J]. Chinese Journal of Organic Chemistry, 2025, 45(5): 1614-1633.