Citation: Chen Yuefeng, Zhao He, Cheng Dongping, Li Xiaonian, Xu Xiaoliang. Coupling of Hantzsch Esters with Baylis-Hillman Derivatives via Visible-Light Photoredox Catalysis[J]. Chinese Journal of Organic Chemistry, ;2020, 40(5): 1297-1304. doi: 10.6023/cjoc201911024 shu

Coupling of Hantzsch Esters with Baylis-Hillman Derivatives via Visible-Light Photoredox Catalysis

a.
College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014
b.
College of Pharmaceutical Science, Zhejiang University of Technology, Hangzhou 310014

Corresponding author: Cheng Dongping, chengdp@zjut.edu.cn Li Xiaonian, xnli@zjut.edu.cn Xu Xiaoliang, xuxiaoliang@zjut.edu.cn
Received Date: 19 November 2019
Revised Date: 17 January 2020
Available Online: 14 February 2020
Fund Project: the Zhejiang Provincial Natural Science Foundation LY15B020004the Zhejiang Provincial Natural Science Foundation LY18B020018the National Natural Science Foundation of China 21602197Project supported by the Zhejiang Provincial Natural Science Foundation (Nos. LY18B020018, LY15B020004) and the National Natural Science Foundation of China (No. 21602197)

Figures(3)

4-Alkyl Hasntzch esters are good alkyl radical storage. The preparation of multisubstituted α, β-unsaturated carboxylic acid esters under photocatalytic redox conditions by 4-alkyl Hantzsch esters and Baylis-Hillman adducts was investigated. The reaction conditions are mild and no additional additives are required. The coupling products were obtained in moderate to good yields.
- visible light photocatalysis,
- radical addition,
- Baylis-Hillman adducts,
- 4-alkyl Hantzsch esters
1. [1]
2. [2]
  (a) Zheng, C.; You, S. L. Chem. Soc. Rev. 2012, 41, 2498.
  (b) Qi, L.; Chen, Y. Angew. Chem., Int. Ed. 2016, 55, 13312.
  (c) Rono, L. J.; Yayla, H. G.; Wang, D. Y.; Armstrong, M. F.; Knowles, R. R. J. Am. Chem. Soc. 2013, 135, 17735.
  (d) Larraufie, M. H.; Pellet, R.; Fensterbank, L.; Goddard, J. P.; Lacôte, E.; Malacria, M.; Ollivier, C. Angew. Chem., Int. Ed. 2011, 50, 4463.
  (e) Zhang, J.; Li, Y.; Zhang, F.; Hu, C.; Chen, Y. Angew. Chem., Int. Ed. 2016, 55, 1872.
  (f) Lee, K. N., Lei, Z.; Ngai, M. Y. J. Am. Chem. Soc. 2017, 139, 5003.
  (g) Wang, P. Z.; Chen, J. R. Xiao, W. J. Org. Biomol. Chem. 2019, 17, 6936.
3. [3]
  (a) Li, G.; Wu, L.; Lv, G.; Liu, H.; Fu, Q.; Zhang, X.; Tang, Z. Chem. Commun. 2014, 50, 6246.
  (b) Chen, W.; Liu, Z.; Tian, J.; Li, J.; Ma, J.; Cheng, X.; Li, G. J. Am. Chem. Soc. 2016, 138, 12312.
  (c) Liu, X.; Liu, R.; Dai, J.; Cheng, X.; Li, G. Org. Lett. 2018, 20, 6906.
  (d) Zhang, H. H.; Zhao, J. J.; Yu, S. J. Am. Chem. Soc. 2018, 140, 16914.
  (e) Wu, Q. Y.; Min, Q. Q.; Ao, G. Z.; Liu, F. Org. Biomol. Chem. 2018, 16, 6391.
  (f) Zhang, H. H.; Yu, S. J. Org. Chem. 2017, 82, 9995.
  (g) Gu, F.; Huang, W.; Liu, X.; Chen, W.; Cheng, X. Adv. Synth. Catal. 2018, 360, 925.
4. [4]
  (a) Nakajima, K.; Nojima, S.; Sakata, K.; Nishibayashi, Y. ChemCatChem 2016, 8, 1028.
  (b) Gutiérrez-Bonet, A.; Tellis, J. C.; Matsui, J. K.; Vara, B. A.; Molander, G. A. ACS Catal. 2016, 6, 8004.
5. [5]
  Song, Z. Y.; Zhang, C. L.; Ye, S. Org. Biomol. Chem. 2019, 17, 181. doi: 10.1039/C8OB02912A
6. [6]
  (a) Reddy, T. N.; Rao, V. J. Tetrahedron Lett. 2018, 59, 2859.
  (b) Yadav, A. K.; Sharma, A. K.; Singh, K. N. Org. Chem. Front. 2019, 6, 989.
  (c) Basavaiah, D.; Reddy, B. S.; Badsara, S. S. Chem. Rev. 2010, 110, 5447.
  (d) Liu, T. Y.; Xie, M.; Chen, Y. C. Chem. Soc. Rev. 2012, 41, 4101.
  (e) Trost, B. M.; Brennan, M. K. Org. Lett. 2007, 9, 3961.
7. [7]
8. [8]
  Li, G.; Chen, R.; Wu, L.; Fu, Q.; Zhang, X.; Tang, Z. Angew. Chem., Int. Ed. 2013, 52, 8432. doi: 10.1002/anie.201303696
9. [9]
  Companyó, X.; Geant, P. Y.; Mazzanti, A.; Moyano, A.; Rios, R. Tetrahedron 2014, 70, 75. doi: 10.1016/j.tet.2013.11.028
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