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Chinese Journal of Organic Chemistry >

0 5010

DOI: https://doi.org/10.6023/cjoc202505010

Synthesis of cis-alkene with electron-withdrawing groups via photocatalytic isomerization

  • Lin Ruhai ,
  • Mao Wei ,
  • Tu Donghuai ,
  • Dong Xingzong ,
  • Ma Hui ,
  • Lu Jian
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  • Xi’an Modern Chemistry Research Institute, State Key Laboratory of Fluorine & Nitrogen Chemical, Xi’an 710065

Received date: 2025-05-08

  Revised date: 2025-06-11

  Online published: 2025-07-18

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Abstract

We report a method for the photocatalytic isomerization synthesis of cis-olefins containing electron-withdrawing groups. The target cis-alkene was synthesized via photocatalytic isomerization using Ir(ppy)₃ as the photosensitizer and 365 nm UV light as the excitation source. This method features mild reaction conditions, high safety, great selectivity, and broad substrate applicability, providing a valuable strategy for the photocatalytic isomerization synthesis of cis-olefin.

Key words： Cis-alkene; photocatalytic isomerization; photosensitizer

Cite this article

Lin Ruhai , Mao Wei , Tu Donghuai , Dong Xingzong , Ma Hui , Lu Jian . Synthesis of cis-alkene with electron-withdrawing groups via photocatalytic isomerization[J]. Chinese Journal of Organic Chemistry, 0 : 5010 . DOI: 10.6023/cjoc202505010

References

[1] Zhang, H.; Yu, S. Y. Chin. J. Org. Chem. 2019, 39, 95.
(张昊, 俞寿云, 有机化学, 2019, 39, 95)
[2] Wittig, G.; Schöllkopf, U. Eur. J. Inorg. Chem. 1954, 87, 1318.
[3] Julia, M.; Paris, J. M. Tetrahedron Lett. 1973, 14, 4833.
[4] Peterson, D. J. J. Org. Chem. 2005, 33, 780.
[5] Koh, M. J.; Khan, R. K. M.; Torker, S.; Amir H. H. Angew. Chem. 2014, 53, 1968.
[6] Lindlar, H. Helv. Chim. Acta. 1952, 35, 446.
[7] Metternich, J. B.; Sagebiel, S.; Lückener, A.; Lamping, S.; Ravoo, B. J.; Gilmour, R. Chem. Eur. J. 2018, 24, 4228.
[8] Corentin, C.; Neiderer, W.; Collins, S. K. ACS Catal. 2021, 11, 8829.
[9] Mlakić, M.; Ljubić, A.; Šalić, A.; Zelić, B.; Horvá, T. O.; MilaŠinović, V.; Gojun, M.; Molčanov, K.; Škorić, I. Catal. 2022, 12, 1510.
[10] Zhang, Q. Q.; Lin, P. P.; Yang, L.; Tan, D. H.; Feng, S. X.; Wang, H. G; Li, Q. J. Chin. J. Org. Chem. 2020, 40, 3314.
(张其奇, 林鹏鹏, 杨羚, 谭东航, 冯嗣欣, 王洪根, 李清江, 有机化学, 2020, 40, 3314)
[11] Cai, W. B.; Fan, H. Q.; Ding, D. Z.; Zhang, Y. Q.; Wang, W. Chem. Commun. 2017, 53, 12918.
[12] Fabender, S. I.; Metternich J. B.; Gilmour, R. Org. Lett. 2018, 20, 724.
[13] Zhang, H.; Huang, C. C.; Yuan, X. A.; Yu, S. Y. J. Am. Chem. Soc. 2022, 144, 10958.
[14] Zhao, X.; Zhong, B.; Dong, L. K.; Zhang, Y. S.; Luo, H. T.; Yang, J. D.; Cheng, J. P. Chem. Eur. J. 2024, 30, 947.
[15] Paul, K.; Franz, M. Z. Tech. Phys. 1931, 12, 593.
[16] Becke, A. D. J. Chem. Phys.1993, 98, 5648.
[17] Ditchfield, R.; Hehre, W. J.; Pople, J. A. J. Chem. Phys. 1971, 54, 724.
[18] Hehre, W. J.; Ditchfield, R.; Pople, J. A. J. Chem. Phys. 1972, 56, 2257.
[19] Hariharan, P. C.; People, J. A. Theor. Chem. Acc. 1973, 28, 213.
[20] Tomasi, J.; Mennucci, B.; Cammi, R. Chem. Rev. 2005, 105, 2999.
[21] Rappe, A. K.; Casewit, C. J.; Colwell, K. S.; Goddard, W. A.; Skiff, W. M. J. Am. Chem. Soc. 1992, 114, 10024.
[22] Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A.; et al. (2016). Gaussian 16, Revision A.03. Gaussian, Inc. Wallingford CT.
[23] Zhao, B.; Zeng, J. J.; Han, S.; Tu, D. H.; Li, J. W.; Zhang, W.; Lu, J. Tetrahedron Lett. 2020, 61, 151693.
[24] Mahmoud, Z.; Ehsan, N.; Ahmad, R. M. Z.; Mohammadm, A. Z. J. Org. Chem. 2018, 7, 3645.
[25] Theresa, H.; John, J. M.; Kathrin, B.; Ryan, G. Org. Lett. 2019, 24, 10164.
[26] Yao, M. L.; Reddy, M. S.; Yong, L.; Walfish, I.; Blevins, D. W.; Kabalka, G. W. Org. Lett. 2010, 4, 700.
[27] Feng, X. J.; Zhang, H. X.; Lu, W. B.; Yamamoto, Y.; Almansour, A. I.; Arumugam, N.; Kumar, R. S.; Bao, M. Synthesis. 2017, 12, 2727.
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