Citation: Lin Mei, Wu Fan, Liu Tianhui, Chen Zhitao, Xu Xiuzhi, Ke Fang. Visible-Light Promoted Preparation of Benzimidazoles by Eosin Y Catalyzed Reaction of Benzonitrile Derivatives in Water[J]. Chinese Journal of Organic Chemistry, ;2020, 40(8): 2563-2569. doi: 10.6023/cjoc202004016 shu

Visible-Light Promoted Preparation of Benzimidazoles by Eosin Y Catalyzed Reaction of Benzonitrile Derivatives in Water

Lin Mei ^a,, ,
Wu Fan ^a ,
Liu Tianhui ^a ,
Chen Zhitao ^a ,
Xu Xiuzhi ^a ,
Ke Fang ^a,b,,

a.
Department of Pharmacy, Fujian Medical University, Fuzhou 350004
b.
Fujian Provincial Key Laboratory of Natural Medicine Pharmacolog, Fuzhou 350004

Corresponding author: Lin Mei, linmei@fjmu.edu.cn Ke Fang, kefang@163.com
Received Date: 11 April 2020
Revised Date: 9 May 2020
Available Online: 25 May 2020
Fund Project: the Natural Science Foundation of Fujian Province 2017J01820the Natural Science Foundation of Fujian Province 2016Y9053Project supported by the Natural Science Foundation of Fujian Province (Nos. 2016Y9052, 2016Y9053, 2017J01820)the Natural Science Foundation of Fujian Province 2016Y9052

Figures(4)

A novel visible-light-introduced reaction for the construction of benzimidazole derivatives via radical cyclization of o-phenylenediamines with benzonitrile derivatives in water has been developed. The reaction has been achieved in high yield under mild conditions by using Eosin Y as photocatalyst, which is cheap, easy to handle and environmentally friendly. A variety of benzimidazoles were obtained in up to 91% yields. It might provide a promising protocol for the synthesis of benzimidazole derivatives.
- visible-light photoredox catalysis,
- eosin Y,
- benzimidazole,
- catalyst
1. [1]
2. [2]
  (a) Algul, O.; Kaessler, A.; Apcin, Y.; Yilmaz, A.; Jose, J. Molecules 2008, 13, 736.
  (b) Khattab, M.; Galal, S. A.; Ragab, F. A. F.; Diwani, H. I. E. Res. Chem. Intermed. 2013, 39, 2917.
  (c) Khalili, S. B.; Sardarian, A. R. Monatsh. Chem. 2012, 143, 841.
  (d) Hu, Z.; Zhao, T.; Wang, M.; Wu, J.; Yu, W.; Chang, J. J. Org. Chem. 2017, 82, 3152.
  (e) Wang, S.; Guan, L.; Zang, J.; Xing, K.; Zhang, J.; Liu, D.; Zhao, L. Molecules 2019, 24, 1198.
3. [3]
  (a) Khosravi, K.; Kazemi, S. Chin. Chem. Lett. 2012, 23, 61.
  (b) Zhang, C.; Zhang, L.-R.; Jiao, N. Green Chem. 2012, 14, 3273.
  (c) Shelkar, R.; Sarode, S.; Nagarkar, J. Tetrahedron Lett. 2013, 54, 6986.
4. [4]
  (a) Rostamizadeh, S.; Amani, A. M.; Aryan, R.; Ghaieni, H. R.; Norouzi, L. Monatsh. Chem. 2009, 140, 547.
  (b) Brasche, G.; Buchwald, S. L. Angew. Chem., Int. Ed. 2008, 120, 1958.
  (c) Martins, G. M.; Puccinelli, T.; Gariani, R. A.; Xavier, F. R.; Silveira, C. C.; Mendes, S. R. Tetrahedron Lett. 2017, 58, 1969.
  (d) Nale, D. B.; Bhanage, B. M. Synlett 2015, 26, 2835.
  (e) De Luca, L.; Porcheddu, A. Eur. J. Org. Chem. 2011, 5791.
5. [5]
  (a) Diao, X.; Wang, Y.; Jiang, Y.; Ma, D. J. Org. Chem. 2009, 74, 7974.
  (b) Xiao, Q.; Wang, W.-H.; Liu, G.; Meng, F.-K.; Chen, J.-H.; Yang, Z.; Shi, Z.-J. Chem.-Eur. J. 2009, 15, 7292.
  (c) Deng, X.; Mani, N. S. Eur. J. Org. Chem. 2010, 2010, 680.
  (d) Wray, B. C.; Stambuli, J. P. Org. Lett. 2010, 12, 4576.
  (e) Bhagat, S. B.; Ghodse, S. M.; Telvekar, V. N. J. Chem. Sci. 2018, 130, 10.
6. [6]
  Qu, Y.; Pan, L.; Wu, Z.; Zhou, X. Tetrahedron 2013, 69, 1717. doi: 10.1016/j.tet.2012.12.039
7. [7]
  Xiang, S.-K.; Zhang, D.-X.; Hu, H.; Shi, J.-L.; Guo, L.-G.; Feng, C.; Wang, B.-Q.; Zhao, K.-Q.; Hu, P.; Yang, H.; Yu, W.-H. Adv. Synth. Catal. 2013, 355, 1495. doi: 10.1002/adsc.201300189
8. [8]
  (a) Wasilke, J.-C.; Obrey, S. J.; Baker, R. T.; Bazan, G. C. Chem. Rev. 2005, 105, 1001.
  (b) Wu, L.; Wang, L.; Chen, P.; Guo, Y.-L.; Liu, G. Adv. Synth. Catal. 2020, 362, 2189.
  (c) Niknam, E.; Panahi, F.; Khalafi-Nezhad, A. Eur. J. Org. Chem. 2020, 2020, 2699.
9. [9]
  (a) Yu, J.; Xia, Y.; Lu, M. Appl. Organomet. Chem. 2014, 28, 764.
  (b) Cao, Z.; Zhu, Q.; Lin, Y.-W.; He, W.-M. Chin. Chem. Lett. 2019, 30, 2132
10. [10]
  Fujishima, A.; Honda, K. Nature (London) 1972, 238, 37.
11. [11]
12. [12]
  (a) Li, L.; Huang, M.; Liu, C.; Xiao, J. C.; Chen, Q. Y.; Guo, Y.; Zhao, Z. G. Org. Lett. 2015, 17, 4714.
  (b) Zhang, M.; Ruzi, R.; Li, N.; Xie, J.; Zhu, C. Org. Chem. Front. 2018, 5, 749.
  (c) Hou, H.; Zhu, S.; Pan, F.; Rueping, M. Org. Lett. 2014, 16, 2872.
13. [13]
  Jana, S.; Verma, A.; Kadu, R.; Kumar, S. Chem. Sci. 2017, 8, 6633. doi: 10.1039/C7SC02556D
14. [14]
  (a) Ke, F.; Xu, Y.; Zhu, S.; Lin, X.; Lin, C.; Zhou, S.; Su, H. Green Chem. 2019, 21, 4329.
  (b) Ke, F.; Liu, C.; Zhang, P.; Xu, J.; Chen, X. Synth. Commun. 2018, 48, 3089.
15. [15]
16. [16]
17. [17]
  (a) Sharghi, H.; Hosseini Sarvari, M.; Moeini, F. Can. J. Chem. 2008, 86, 1044.
  (b) Sharghi, H.; Aberi, M.; Doroodmand, M. M. Adv. Synth. Catal. 2008, 350, 2380.
  (c) Chen, Y. X.; Qian, L. F.; Zhang, W.; Han, B. Angew.
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