SIOC 中文
CJOG
Adv search

Chinese Journal of Organic Chemistry >

0 202604019

DOI: https://doi.org/10.6023/cjoc202604019

ARTICLE

Visible-Light Promoted Bromotrifluoromethylation Reaction of CF3Br with Unactivated Alkenes

  • Zhao Mingqi ,
  • Huang Danfeng ,
  • Wen Huan ,
  • Zhang Dan ,
  • Wang Ke-Hu ,
  • Wang Junjiao ,
  • Zhang Bo-Sheng ,
  • Hu Yulai
Expand
  • College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou 730070

Received date: 2026-04-12

  Revised date: 2026-06-04

  Online published: 2026-08-17

Supported by

National Natural Science Foundation of China (Nos. 22461038).

Fold

Abstract

A visible-light promoted bromotrifluoromethylation reaction of CF3Br with unactivated alkenes was achieved in the presence of catalytic amount of fac-IrIII(ppy)3. In the reaction, CF3Br serves as a bifunctional reagent to provide both the CF3 group and bromine source. The method features high regioselectivity, mild reaction conditions, high atom economy and good yields, which offers an economical and practical method for the construction of structurally diverse β-trifluoromethylated alkyl bromides.

Key words： visible-light catalysis; CF3Br; unactivated alkenes; bromotrifluoromethylation; bifunctional trifluoromethylating reagents

Cite this article

Zhao Mingqi , Huang Danfeng , Wen Huan , Zhang Dan , Wang Ke-Hu , Wang Junjiao , Zhang Bo-Sheng , Hu Yulai . Visible-Light Promoted Bromotrifluoromethylation Reaction of CF3Br with Unactivated Alkenes[J]. Chinese Journal of Organic Chemistry, 0 : 202604019 . DOI: 10.6023/cjoc202604019

References

[1] (a) Zhou Y.; Wang J.; Gu Z.; Wang S.; Zhu W.; Aceña J. L.; Soloshonok V. A.; Izawa K.; Liu H. Chem. Rev.2016, 116, 422-518.
(b) Purser S.; Moore P. R.; Swallow S.; Gouverneur, V. Chem. Soc. Rev.2008, 37, 320-330.
(c) Müller K.; Faeh C.; Diederich F. Science2007, 317, 1881-1886.
[2] (a) Zhang Y.; Zhou Z.-L.; Li J.-H.; Li Y.-T. Chem. Rec.2025, 25, e202400263.
(b) Wang Y.; Bao Z-P.; Mao X-D.; Hou M.; Wu, X-F. Chem. Soc. Rev.2025, 54, 9530-9573.
(c) Zhou Z.-L.; Zhang Y.; Cui P.-Z.; Li, J.-H. Chem. Eur. J.2024, 30, e202402458.
[3] (a) Alvarez E. A.; Li J.; Malapit, C. A. Angew. Chem. Int. Ed.2025, 64, e202415218.
(b) Gao C.; Kong F.-L.; Xu C.; Wang M. Org. Lett.2025, 27, 6007-6012.
(c) Yang Y.-F.; Lin J.-H.; Xiao J.-C. Org. Lett.2021, 23, 9277-9282.
[4] (a) He Y.; Bian K.-J.; Wu B.-B.; Liu P.; Ni S.-X.; Wang, X.-S. Chin. J. Chem.2022, 40, 1531-1536.
(b) Zhang Z.; Zhu L.; Li, C. Chin. J. Chem.2019, 37, 452-456.
(c) He Y.-T.; Kang D.; Kim I.; Hong S. Green Chem.2018, 20, 5209-5214.
[5] (a) Behera M.; Dharpure P. P.; Sahu A. K.; Bhat, R. G. J. Org. Chem.2024, 89, 14695-14709.
(b) Su Z.; Guo Y.; Chen Q.-Y.; Zhao Z.-G.; Nian, B.-Y. Chin. J. Chem.2019, 37, 597-604.
(c) Yasu Y.; Arai Y.; Tomita R.; Koike T.; Akita M. Org. Lett.2014, 16, 780-783.
(d) Jiang X.-Y.; Qin, F.-L. Angew. Chem. Int. Ed.2013, 52, 14177-14180.
[6] (a) Yu, Z.-L.; Tan, Y.; Chen, J.-X.; Liu, Z.-J.; Liang, X.; Xiao, H.-S.; Wang, Q.; Wang, X.-J. Org. Lett. 2026, 28, 2109-2114.
(b) Choi, Y. R.; Kang, S.; Hwang, J.; An, H.; Hong, K. B.ACS Omega 2024, 9, 47500-47505.
(c) Zhang M.; Lin J.-H.; Xiao J.-C. Org. Lett.2021, 23, 6079-6083.
(d) Wang, P.; Zhu, S.; Lu, D.; Gong, Y. Org. Lett. 2020, 22, 1924-1928.
(e) Xiao W.; Shen H.; Zhu L.; Li, C. J. Am. Chem. Soc.2019, 141, 11440-11445.
[7] Kareem R. T.; Azizi B.; Asnaashariisfahani M.; Ebadi A.; Vessally E. RSC Adv.2021, 11, 14941-14955.
[8] Gál B.; Bucher C.; Burns, N. Z. Mar. Drugs2016, 14, 206-215.
[9] (a) Su W.; Cui J.; Zeng R. ChemistryOpen2023, 12, e202300068.
(b) Fu M.; Chen L.; Jiang Y.; Jiang Z.-X.; Yang Z. Org. Lett.2016, 18, 348-351.
(c) Egami, H.; Usui, Y.; Kawamura, S.; Nagashima, S.; Sodeoka, M. Chem. Asian J. 2015, 10, 2190-2199.
[10] (a) Liu Z.; Chen H.; Lv Y.; Tang X.; Shen H.; Yu H.-Z.; Li, C. J. Am. Chem. Soc.2018, 140, 6169-6175.
(b) An W.; Ha N.; Lee H. M.; Malpani Y. R.; Lee D.-H.; Jung Y.-S.; Han, S. B. Adv. Synth. Catal.2015, 357, 3949-3960.
(c) Carboni A.; Dagousset G.; Magnier E.; Masson G. Synthesis2015, 47, 2439-2445.
[11] (a) Lu Y.; Liu Z.; Liu C.; Wu Y.; Li L.; Liu S.; Wang, H. Gao W.; Liu Z.; Chen, J. Org. Chem. Front.2023, 10, 1283-1288.
(b) Sun H.; Cui G.; Shang H.; Cui, B. J. Org. Chem.2020, 85, 15241-15255.
(c) Ye, K.-Y.; Pombar, G.; Fu, N.; Sauer, G. S.; Keresztes, I.; Lin, S.J. Am. Chem. Soc. 2018, 140, 2438-2441.
(d) Fang J.; Wang Z.-K.; Wu S.-W.; Shen W.-G.; Ao G.-Z.; Liu F. Chem. Commun.2017, 53, 7638-7641.
(e) Liu Z.-Q.; Liu, D. J. Org. Chem.2017, 82, 1649-1656.
(f) Yang B.; Xu X.-H.; Qing, F.-L. Chin. J. Chem.2016, 34, 465-468.
(g) Hang Z.; Li Z.; Liu Z.-Q. Org. Lett.2014, 16, 3648-3651.
[12] Guo G.-Y.; Wu R.-X.; Jin J.-K.; Tian S.-K. Org. Lett.2016, 18, 3850-3853.
[13] Yu, W.; Xu, X.-H.; Qing, F.-L. Adv. Synth. Catal. 2015, 357, 2039-2044.
[14] (a) Maiti R.; Nath A.; Guimarães A. B. R.; Bagnich S.; KÖhler A.; Maseras F.; Das, S. J. Am. Chem. Soc.2025, 147, 38021-38032.
(b) Ran X.-J.; Liao P.-W.; Sheng H.; Wang Z.-X.; Chen X.-Y. Org. Lett.2023, 25, 6189-6194.
(c) Alkan-Zambada M.; Hu X. Organometallics2018, 37, 3928-3935.
(d) Bagal D. B.; Kachkovskyi G.; Knorn M.; Rawner T.; Bhanage B. M.; Reiser, O. Angew. Chem. Int. Ed.2015, 54, 6999-7002.
(e) Tang X.-J.; Dolbier, Jr. W. R. Angew. Chem. Int. Ed.2015, 54, 4246-4249.
(f) Oh S. H.; Malpani Y. R.; Ha N.; Jung Y.-S.; Han, S. B. Org. Lett.2014, 16, 1310-1313.
[15] (a) Ol’shevskaya V. A.; Tyutyunov A. A.; Ibragimova L. F.; Kononova E. G.; Rys E. G. Polyhedron.2019, 171, 508-514.
(b) Huang W.-Y.; Lv, L. Chin. J. Chem.1992, 10, 268-273.
[16] (a) Rawner T.; Lutsker E.; Kaiser C. A.; Reiser O. ACS Catal.2018, 8, 3950-3956.
(b) Xu T.; Cheung, C. W. Hu, X. Angew. Chem. Int. Ed.2014, 53, 4910-4914.
(c) Ignatowska J.; Dmowski, W. J. Fluorine Chem.2007, 128, 997-1006.
[17] Xu C.; Huang W.; Zhang R.; Gao C.; Li Y.; Wang, M. J. Org. Chem.2019, 84, 14209-14216.
[18] (a) Takeyama Y.; Ichinose Y.; Oshima K.; Utimoto K. Tetrahedron Lett.1989, 30, 3159-3162.
(b) Maruoka, K.; Sano, Y.; Fukutani, Y.; Yamamoto, H.Chem. Lett. 1985, 1689-1692.
[19] (a) Beniazza R.; Douarre M.; Lastécouères D.; Vincent J.-M. Chem. Commun.2017, 53, 3547-3550.
(b) Beniazza R.; Remisse L.; Jardel D.; Lastécouères D.; Vincent J.-M. Chem. Commun.2018, 54, 7451-7454.
[20] Kostromitin V. S.; Zemtsov A. A.; Kokorekin V. A.; Levin V. V.; Dilman, A. D. Chem. Commun.2021, 57, 5219-5222.
[21] Caron, S. Org. Process Res. Dev.2020, 24, 470-480.
[22] Ma R.; Deng Z.; Wang K.-H.; Huang D.; Hu Y.; Lv, X. Chin. J. Org. Chem.2022, 42, 353-362.
(马然松, 邓周斌, 王克虎, 黄丹凤, 胡雨来, 闾肖波, 有机化学. 2022, 42, 353-362.)
[23] (a) Zhu Z.; Lv Y.; Deng Z.; Wang J.; Wang K-H.; Zhang B.; Huang D.; Hu, Y. J. Org. Chem.2026, 91, 1119-1129.
(b) Ren Y.; Zhou Y.; Wang K.-H.; Wang J.; Huang D.; Hu Y. Org. Lett.2025, 27, 7033-7038.
(c) Zhou Y.; Ren Y.; Wang K-H.; Wang J.; Huang D.; Hu, Y. J. Org. Chem.2025, 90, 13520-13524.
(d) Ren Y.; Zhou Y.; Wang K.-H.; Wang J.; Huang D.; Hu, Y. J. Org. Chem.2025, 90, 3739-3744.
(e) Lv Y.; Deng Z.; Zhu Z.; Wang J.; Wang K-H.; Huang D.; Hu, Y. J. Org. Chem.2024, 89, 18452-18463.
[24] Ma R.; Ren Y.; Deng Z.; Wang K-H.; Wang J.; Huang D.; Lv X.; Hu Y. Org. Lett.2023, 25, 4080-4085.
[25] (a) Yuan Y.; Faure C.; Berthelot M.; Belmont P.; Brachet, E. J. Org. Chem.2024, 89, 3538-3545.
(b) Bao, P.; Niu, L.; Zhang, W.; Li, S.-J.; Lan, Y. ChemRxiv. 13 November 2024. doi.org/10.26434/chemrxiv-2024-t1tm5.
[26] (a) Du Y.-M.; Chen X.-Y.; Li Y.; Koh M.; Shu W. Nat. Commun.2025, 16, 4163-4171.
(b) Liang J.; Feng Z.; Liu Y.; Chen Z.; Li W.; Wang C. Org. Lett.2025, 27, 10836-10842.
(c) Andolina S.; Puglisi A.; Rossi S.; Medici F.; Benaglia, M. Org. Chem. Front.2025, 12, 7055-7063.
(d) Leung V. M.-Y.; Wong H.-C. F.; Pook C.-M.; Tse Y.-L. S.; Yeung Y.-Y. Chem. Sci.2023, 14, 12684-12692.
(e) Bhoyare, V. W.; Sosa Carrizo, E. D.; Chintawar, C. C.; Gandon, V.; Patil, N. T.J. Am. Chem. Soc. 2023, 145, 8810-8816.
(f) Bonaparte A. C.; Betush M. P.; Panseri M. B.; Mastarone D. J.; Murphy R. K.; Murphree, S. S. Org. Lett.2011, 13, 1447-1449.
Options
Outlines

/

〈 〉