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Chinese Journal of Organic Chemistry >

0 9004

DOI: https://doi.org/10.6023/cjoc202509004

ARTICLE

Electrochemical radical dienylation reaction of arylphosphine oxides

  • Wang Xinyu ,
  • Huang Chenpei ,
  • Guo Chang ,
  • Song Jin
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  • aInstitutes of Physical Science and Information Technology, Anhui University, Hefei 230601;
    bHefei National Laboratory for Physical Sciences at the Microscale, University of Science and Technology of China, Hefei, 230026

Received date: 2025-09-04

  Revised date: 2025-10-22

  Online published: 2025-11-27

Supported by

National Natural Science Foundation of China (No.22471002) and Anhui Provincial Natural Science Foundation (No.2308085Y12), and Undergraduate Students Project of Anhui Province (No.S202510357568).

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Abstract

The development of straightforward and environmentally friendly techniques for synthesizing organophosphorus compounds with C(sp2)-P bonds would be of great value for the advancement of synthetic chemistry. Herein, we report an electrochemically driven dienylation strategy of arylphosphine oxides with allenylsilanes for the efficient synthesis of dienyl phosphorus compounds. A wide range of dienyl organophosphorus compounds with various functional group tolerance were facilely obtained in moderate to great yield. Mechanistic studies indicate that the desired C(sp2)-P bond is constructed through the radical addition process between the phosphoryl radical and the allene carbon.

Key words： electrochemical; dienylation; phosphoryl radical; C(sp2)-P bond

Cite this article

Wang Xinyu , Huang Chenpei , Guo Chang , Song Jin . Electrochemical radical dienylation reaction of arylphosphine oxides[J]. Chinese Journal of Organic Chemistry, 0 : 9004 . DOI: 10.6023/cjoc202509004

References

[1] For recent reviews: (a) Tang, W.; Zhang, X. Chem. Rev. 2003, 103, 3029-3070.
(b) Xie, J.-H.; Zhou, Q.-L. Acc. Chem. Res. 2008, 41, 581-593.
(c) Fernández-Pérez, H.; Etayo, P.; Panossian, A.; Vidal-Ferran, A. Chem. Rev. 2011, 111, 2119-2176.
(d) Monge, S.; David, G. Phosphorus-Based Polymers from Synthesis to Applications; The Royal Society of Chemistry: Cambridge, 2014.
[2] (a) Alonso F.; Beletskaya I. P.; Yus M. Chem. Rev.2004, 104, 3079-3160.
(b) Cai, B.-G.; Xuan, J.; Xiao, W.-J. Science Bulletin 2019, 64, 337-350.
[3] (a) Leca D.; Fensterbank L.; Lacote E.; Malacria, M. Chem. Soc. Rev. 2005, 34, 858-865.
(b) Marque S.; Tordo, P. Top. Curr. Chem.2005, 250, 43.
(c) Mondal, M.; Bora, U. RSC Adv. 2013, 3, 18716-18754.
(d) Gao, Y.; Tang, G.; Zhao, Y. Phosphorus Sulfur. Silicon Relat. Elem. 2017, 192, 589-596.
(e) Gao, Y.; Tang, G.; Zhao, Y. Chin J. Org. Chem. 2018, 38, 62-74.
[4] (a) Pan X.-Q.; Zou J.-P.; Zhang G.-L.; Zhang W. Chem. Commun.2010, 46, 1721-1723.
(b) Mao L.-L.; Zhou A.-X.; Liu N.; Yang S.-D. Synlett2014, 25, 2727-2732.
(c) Unoh, Y.; Hirano, K.; Satoh, T.; Miura, M. Angew. Chem. Int. Ed. 2013, 52, 12975-12979.
(d) Mi, X.; Wang, C.; Huang, M.; Zhang, J.; Wu, Y.; Wu, Y. Org. Lett. 2014, 16, 3356-3359.
(e) Zhu, X.-T.; Zhao, Q.; Liu, F.; Wang, A.-F.; Cai, P.-J.; Hao, W.-J.; Tu, S.-J.; Jiang, B. Chem. Commun. 2017, 53, 6828-6831.
(f) Xu, P.; Wu, Z.; Zhou, N.; Zhu, C. Org. Lett. 2016, 18, 1143-1145.
(g) Yang, S.-N.; Sun, S.-H.; Liu, C.-H.; Min, X.-T.; Wan, B.; Ji, D.-W.; Chen, Q.-A. Chin. Chem. Lett. 2023, 34, 107914.
[5] (a) Li J.; Zhao J.; Loh T.-P. Synlett2024, 35, 840-850.
(b) Quint, V.; Morlet-Savary, F.; Lohier, J.-F.; Lalevée, J.; Gaumont, A.-C.; Lakhdar, S. J. Am. Chem. Soc. 2016, 138, 7436-7441.
(c) Kim, I.; Min, M.; Kang, D.; Kim, K.; Hong, S. Org. Lett. 2017, 19, 1394-1397.
(d) Liao, L.-L.; Gui, Y.-Y.; Zhang, X.-B.; Shen, G.; Liu, H.-D.; Zhou, W.-J.; Li, J.; Yu, D.-G. Org. Lett. 2017, 19, 3735-3738.
(e) Liu, D.; Chen, J.-Q.; Wang, X.-Z.; Xu, P.-F. Adv. Synth. Catal. 2017, 359, 2773-2777.
(f) Xie, P.; Fan, J.; Liu, Y.; Wo, X.; Fu, W.; Loh, T.-P. Org. Lett. 2018, 20, 3341-3344.
(g) Wang, H.; Li, Y.; Tang, Z.; Wang, S.; Zhang, H.; Cong, H.; Lei, A. ACS Catal. 2018, 8, 10599-10605.
(h) Liu, W.-Q.; Lei, T.; Zhou, S.; Yang, X.-L.; Li, J.; Chen, B.; Sivaguru, J.; Tung, C.-H.; Wu, L.-Z. J. Am. Chem. Soc. 2019, 141, 13941-13947.
(i) Yang, W.; Li, B.; Zhang, M.; Wang, S.; Ji, Y.; Dong, S.; Feng, J.; Yuan, S. Chin. Chem. Lett. 2020, 31, 1313-1316.
(j) Hou, H.; Zhou, B.; Wang, J.; Zhao, D.; Sun, D.; Chen, X.; Han, Y.; Yan, C.; Shi, Y.; Zhu, S. Org. Lett. 2021, 23, 2981-2987.
(k) Ma, W.; Zhang, S.; Xu, L.; Zhang, B.; Li, G.; Rao, B.; Zhang, M.; He, G. Chin. Chem. Lett. 2023, 34, 107958.
(l) Yang, T.-M.; Fan, X.-L.; Shi, W.; Zhao, X.; Hu, X.-H. Green Chem. 2024, 26, 11272-11279.
[6] (a) Yoshida J.-I.; Kataoka K.; Horcajada R.; Nagaki, A. Chem. Rev. 2008, 108,2265-2299.
(b) Francke, R.; Little, D.Chem. Soc. Rev. 2014, 43, 2492-2521.
(c) Yan, M.; Kawamata, Y.; Baran, P. S. Chem. Rev. 2017, 117, 13230-13319.
(d) Jiang, Y.; Xu, K.; Zeng, C. Chem. Rev. 2018, 118, 4485-4540.
(e) Waldvogel, S. R.; Lips, S.; Selt, M.; Riehl, B.; Kampf, C. J. Chem. Rev. 2018, 118, 6706-6765.
(f) Tang, S.; Liu, Y.; Lei, A. Chem 2018, 4, 27-45.
(g) Chang, X.; Zhang, Q.; Guo, C. Angew. Chem. Int. Ed. 2020, 59, 12612-12622.
(h) Kim, Y.; Li, C.-J. Green Synth. Catal. 2020, 1, 1-11.
[7] (a) Sbei N.; Martins G. M.; Shirinfar B.; Ahmed N. Chem. Rec.2020, 20, 1530-1552.
(b) Budnikova, Y. H.; Dolengovsky, E. L.; Tarasov, M. V.; Gryaznova, T. V. Front. Chem. 2022, 10, 1054116.
[8] (a) Hu C.; Hong G.; Zhou C.; Tang Z.-C.; Han J.-W.; Wang, L.-M. Asian J. Org. Chem.2019, 8, 2092-2096.
(b) Li, K.-J.; Jiang, Y.-Y.; Xu, K.; Zeng, C.-C.; Sun, B.-G. Green Chem. 2019, 21, 4412-4421.
[9] (a) Lu L.; Fu N.; Lin, S. Synlett 2019, 30,1199-1203.
(b) Zhou, X.; Wang, J.; Ma, D.; Shen, Y.; Zhao, Y.; Wu, J.;Chem. Commun. 2024, 60, 7351-7354.
[10] (a) Xu Z.; Li Y.; Mo G.; Zheng Y.; Zeng S.; Sun P.-H.; Ruan Z. Org. Lett.2020, 22, 4016-4020.
(b) Liu, T.; Lin, J.; Xia, F.; Xu, Z.; Xia, X.; Qian, W.; Zhong, W.; Song, D.; Ling, F. Green Synth. Catal. 2024, 5, 297-302.
[11] (a) Zhang Q.; Zhang J.; Zhu W.; Lu R.; Guo C. Nat. Commun.2024, 15, 4477.
(b) Huang, J.; Wang, Q.; Wang, X.; Song, J.; Guo, C. ChemCatChem 2024, 16, e202401650.
[12] (a) Wang H.; Beiring B.; Yu D.-G.; Collins K.-D.; Glorius, F. Angew. Chem. Int. Ed.2013, 52, 12430-12434.
(b) Shan, Q.-C.; Hu, L.-M.; Qin, W.; Hu, X.-H. Org. Lett. 2021, 23, 6041-6045.
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