Citation: Liu Lice, Wu Jieqing, Ma Hongfei, Zhang Han, Gu Jiefan, Li Yufeng. Nickel Chloride-Catalyzed Oxidation of Aromatic Hydrocarbon with Sodium Persulfate at the Benzylic Site[J]. Chinese Journal of Organic Chemistry, ;2019, 39(6): 1688-1694. doi: 10.6023/cjoc201903003 shu

Nickel Chloride-Catalyzed Oxidation of Aromatic Hydrocarbon with Sodium Persulfate at the Benzylic Site

Liu Lice ^a ,
Wu Jieqing ^a ,
Ma Hongfei ^a ,
Zhang Han ^b ,
Gu Jiefan ^a ,
Li Yufeng ^a,,

a.
College of Chemistry and Molecular Engineering, Nanjing Tech University, Nanjing 210036
b.
Nanjing UNOCI Chemical Co., Nanjing 210009

Corresponding author: Li Yufeng, yufengli@njtech.edu.cn
Received Date: 2 March 2019
Revised Date: 18 April 2019
Available Online: 26 June 2019

Figures(2)

A practical method for the oxidation of aromatic side chains was established for the preparation of aromatic aldehydes and ketones. Using NiCl₂ as the catalyst, substituted toluenes were oxidized with Na₂S₂O₈ at the benzylic site for the synthesis of the corresponding aldehydes in the yield of 22%~79%. Ethylbenzene analogs were oxidized more easily to obtain the corresponding ketones with 64%~84% yields. The oxidation of benzyl alcohol analogs was completed to acquire the corresponding carbonyl compounds in shorter time with better selectivity and yields. The method has the advantages such as the mild reaction conditions, no requirement for precious metals or additional promoter, and good selectivity.
- oxidation,
- aromatic hydrocarbon,
- benzyl alcohol,
- nickel chloride,
- sodium persulfate
1. [1]
  (a) Sheldon, R. A.; Kochi, J. K. Metal Catalyzed Oxidations of Organic Compounds, Academic Press, New York, 1981.
  (b) Trost, B. M.; Fleming, I. Comprehensive Organic Synthesis (Oxidation), Pergamon, New York, 1991, Vol. 7.
  (c) Zhang, J. T.; Wang, Z. T.; Wang, L.; Wan, C. F.; Zheng, X. Q.; Wang, Z. Y. Green. Chem. 2009, 11, 1973.
2. [2]
  Rao, K. T. V.; Rao, P. S. N.; Nagaraju, P.; Prasad, P. S. S.; Lingaiah, N. J. Mol. 2009, 303, 84. doi: 10.1016/j.molcata.2009.01.006
3. [3]
  (a) Anastas, P.; Eghbali, N. Chem. Soc. Rev. 2010, 39, 301.
  (b) Yiu, S. M.; Wu, Z. B.; Mak, C. K.; Lau, T. C. J. Am. Chem. Soc. 2004, 126, 14921.
  (c) Hudlicky, M. Oxidations in Organic Chemistry, American Chemical Society, Washington, DC, 1990.
4. [4]
5. [5]
  (a) Ohkubo, K.; Fukuzumi, S. Org. Lett. 2000, 2, 3647.
  (b) Kei, O.; Kyou, S.; Kohei, M.; Shunichi, F. J. Am. Chem. Soc. 2003, 125, 12850.
  (c) Pahari, S. K.; Pal, P.; Srivastava, D. N.; Ghosh, S. C.; Panda, A. B. Chem. Commun. 2015, 51, 10322.
  (d) Li, S. L.; Zhu, B.; Lee, R.; Qiao, B. K.; Jiang, Z. Y. Org. Chem. Front. 2018, 5, 380.
6. [6]
  (a) Jr, L. Q.; Tolman, W. B. Nature 2008, 455. 333.
  (b) Rickert, A.; Krombach, V.; Hamers, O.; Zorn, H.; Maison, W. G. Green Chem. 2012, 14, 639.
  (c) Roiban, G. D.; Agudo, R.; Reetz, M. T. Angew. Chem., Int. Ed. 2014, 53, 8659.
  (d) Nastri, F.; Chino, M.; Maglio, O.; Damodaran, A. B.; Lu, Y.; Lombardi, A. Chem. Soc. Rev. 2016, 45, 5020.
7. [7]
  (a) Nam, W. Acc. Chem. Res. 2007, 40, 522.
  (b) Ding, Z. D.; Zhu, W.; Li, T.; Shen, R.; Li, Y. X.; Li, Z. J.; Ren, X. H.; Gu, Z. G. Dalton Trans. 2017, 46, 11372.
8. [8]
  (a) Qi, J. Y.; Ma, H. X.; Li, X. J.; Zhou, Z. Y.; Choi, M. C. K.; Chan, A. S. C.; Yang, Q. Y. Chem. Commun. 2003, 1294.
  (b) Wang, B.; Mao, W.; Ma, H. Z. Ind. Eng. Chem. Res. 2009, 48, 440.
  (c) Potapenko, E. V.; Andreev, P. Y. Russ. J. Appl. Chem. 2011, 84, 984.
9. [9]
  (a) Lane, B.-S.; Burgess, K. Chem. Rev. 2003, 103, 2457.
  (b) Wang, Y.; Li, H. R.; Yao, J.; Wang, X. C.; Antoniettia, M. Chem. Sci. 2011, 2, 446.
  (c) Shen, D. Y.; Miao, C. X.; Wang, S. F.; Xia, C. G.; Sun, W. Org. Lett. 2014, 16, 1108.
  (d) Verma, S.; Baig, R. B. N.; Nadagouda, M. N.; Varma, R. S. ACS Sustainable Chem. Eng. 2016, 4, 2333.
  (e) Saisaha, P.; Dong, J. J.; Meinds, T. G.; Johannes, W.; Hage, R.; Mecozzi, F.; Kasper, J. B.; Browne, W. R. ACS Catal. 2016, 6, 3486.
  (f) Konstantin, P.; Bryliakov Chem. Rev. 2017, 117, 11406.
10. [10]
  (a) Halina, W.; Soroko, G.; Jacek, M. Synth. Commun. 2008, 38, 2000.
  (b) Hossain, M. M.; Shyu, S. G. Tetrahedron 2016, 72, 4252.
  (c) Xu, W. X.; Zhang, Z. Q.; Zhao, X.; Li, J. Coord. Chem. 2017, 70, 746.
  (d) Chen, Y.; Jie, S. S.; Yang, C. Q.; Liu, Z. G. Appl. Surf. Sci. 2017, 419, 98.
  (e) Sun, Q.; Song, X. Y.; Gao, L.; Chen, W.; Li, Y.; Mao, L.; Yang, J. H. Chem. Pap. 2018, 72, 2203.
11. [11]
  (a) Badri, R.; Adlu, M.; Mohammadi, M. K. Arabian J. Chem. 2015, 8, 62.
  (b) Hu, Y. X.; Zhou, L. H.; Lu, W. J. Synthesis 2017, 49, 4007.
  (c) Han, W.; Zhao, H. Y. CN 107216242, 2017[Chem. Abstr. 2017, 167, 528688].
12. [12]
  Jakob, H.; Leininger, S.; Lehmann, T.; Jacobi, S.; Gutewort, S. Ullmann's Encyclopedia of Industrial Chemistry, Weinheim, W. C. Germany, 2012, Vol. 26, p. 308.
13. [13]
  Li, Y. F.; Zhang, H.; Dai, C. W.; Liu, L. C.; Ma, H. F.; Pu, H. Z. Tetrahedron 2018, 74, 3712. doi: 10.1016/j.tet.2018.05.045
14. [14]
  Lin, X.; Nie, Z. Z.; Zhang, L. Y.; Mei, S. C.; Chen, Y. Green Chem. 2017, 19, 2164. doi: 10.1039/C7GC00469A
15. [15]
  Zhang, B. S.; Zhu, R. L.; Liu, Z. G.; Xin, L.; Zhang, J. S. Org. Chem. Front. 2016, 3, 1326. doi: 10.1039/C6QO00237D
16. [16]
  Guo, T. F.; Gao, Y.; Li, Z. J.; Liu, J. J.; Guo, K. Synlett 2019, 30, 329. doi: 10.1055/s-0037-1611183
17. [17]
  Gholizadeh, M.; Baltork, I. M. Bull. Korean Chem. Soc. 2005, 26, 11.
18. [18]
  Castle, R. N.; Riebsomer, J. L. ACS Sustainable Chem. Eng. 1955, 21, 142.
19. [19]
  Richard, R. B.; Louise, J. B. J. Anal. Appl. Pyrolysis 2004, 71, 223. doi: 10.1016/S0165-2370(03)00090-1
20. [20]
  Cui, L. Q.; Liu, K.; Zhang, C. Org. Biomol. Chem. 2011, 9, 2258. doi: 10.1039/c0ob00722f
21. [21]
  Kaneyuki, H. Bull. Chem. Soc. Jpn. 1961, 35, 519.
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