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.
1. [1]
  Peng YUE , Liyao SHI , Jinglei CUI , Huirong ZHANG , Yanxia GUO . Effects of Ce and Mn promoters on the selective oxidation of ammonia over V₂O₅/TiO₂ catalyst. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 293-307. doi: 10.11862/CJIC.20240210
2. [2]
  Peiyu Zhang , Aixin Song , Jingcheng Hao , Jiwei Cui . 高频超声法制备聚多巴胺薄膜综合实验. University Chemistry, 2025, 40(6): 210-214. doi: 10.12461/PKU.DXHX202407081
3. [3]
  Xiaofei Liu , He Wang , Li Tao , Weimin Ren , Xiaobing Lu , Wenzhen Zhang . Electrocarboxylation of Benzylic Phosphates and Phosphinates with Carbon Dioxide. Acta Physico-Chimica Sinica, 2024, 40(9): 2307008-0. doi: 10.3866/PKU.WHXB202307008
4. [4]
  Jiarui Wu , Gengxin Wu , Yan Wang , Yingwei Yang . Crystal Engineering Based on Leaning Towerarenes. University Chemistry, 2024, 39(3): 58-62. doi: 10.3866/PKU.DXHX202304014
5. [5]
  Zhanggui DUAN , Yi PEI , Shanshan ZHENG , Zhaoyang WANG , Yongguang WANG , Junjie WANG , Yang HU , Chunxin LÜ , Wei ZHONG . Preparation of UiO-66-NH₂ supported copper catalyst and its catalytic activity on alcohol oxidation. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 496-506. doi: 10.11862/CJIC.20230317
6. [6]
  Yinjie Xu , Suiqin Li , Lihao Liu , Jiahui He , Kai Li , Mengxin Wang , Shuying Zhao , Chun Li , Zhengbin Zhang , Xing Zhong , Jianguo Wang . Enhanced Electrocatalytic Oxidation of Sterols using the Synergistic Effect of NiFe-MOF and Aminoxyl Radicals. Acta Physico-Chimica Sinica, 2024, 40(3): 2305012-0. doi: 10.3866/PKU.WHXB202305012
7. [7]
  Rong Tian , Yadi Yang , Naihao Lu . Comprehensive Experimental Design of Undergraduate Students Based on Interdisciplinarity: Study on the Effect of Quercetin on Chlorination Activity of Myeloperoxidase. University Chemistry, 2024, 39(8): 247-254. doi: 10.3866/PKU.DXHX202312064
8. [8]
  Bo YANG , Gongxuan LÜ , Jiantai MA . Nickel phosphide modified phosphorus doped gallium oxide for visible light photocatalytic water splitting to hydrogen. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 736-750. doi: 10.11862/CJIC.20230346
9. [9]
  Qingqing SHEN , Xiangbowen DU , Kaicheng QIAN , Zhikang JIN , Zheng FANG , Tong WEI , Renhong LI . Self-supporting Cu/α-FeOOH/foam nickel composite catalyst for efficient hydrogen production by coupling methanol oxidation and water electrolysis. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1953-1964. doi: 10.11862/CJIC.20240028
10. [10]
  Meiran Li , Yingjie Song , Xin Wan , Yang Li , Yiqi Luo , Yeheng He , Bowen Xia , Hua Zhou , Mingfei Shao . Nickel-Vanadium Layered Double Hydroxides for Efficient and Scalable Electrooxidation of 5-Hydroxymethylfurfural Coupled with Hydrogen Generation. Acta Physico-Chimica Sinica, 2024, 40(9): 2306007-0. doi: 10.3866/PKU.WHXB202306007
11. [11]
  Hailang JIA , Pengcheng JI , Hongcheng LI . Preparation and performance of nickel doped ruthenium dioxide electrocatalyst for oxygen evolution. Chinese Journal of Inorganic Chemistry, 2025, 41(8): 1632-1640. doi: 10.11862/CJIC.20240398
12. [12]
  Yi Yang , Xin Zhou , Miaoli Gu , Bei Cheng , Zhen Wu , Jianjun Zhang . Femtosecond transient absorption spectroscopy investigation on ultrafast electron transfer in S-scheme ZnO/CdIn₂S₄ photocatalyst for H₂O₂ production and benzylamine oxidation. Acta Physico-Chimica Sinica, 2025, 41(6): 100064-0. doi: 10.1016/j.actphy.2025.100064
13. [13]
  Xinhao Yan , Guoliang Hu , Ruixi Chen , Hongyu Liu , Qizhi Yao , Jiao Li , Lingling Li . Polyethylene Glycol-Ammonium Sulfate-Nitroso R Salt System for the Separation of Cobalt (II). University Chemistry, 2024, 39(6): 287-294. doi: 10.3866/PKU.DXHX202310073
14. [14]
  Yan LIU , Jiaxin GUO , Song YANG , Shixian XU , Yanyan YANG , Zhongliang YU , Xiaogang HAO . Exclusionary recovery of phosphate anions with low concentration from wastewater using a CoNi-layered double hydroxide/graphene electronically controlled separation film. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1775-1783. doi: 10.11862/CJIC.20240043
15. [15]
  Bizhu Shao , Huijun Dong , Yunnan Gong , Jianhua Mei , Fengshi Cai , Jinbiao Liu , Dichang Zhong , Tongbu Lu . Metal-Organic Framework-Derived Nickel Nanoparticles for Efficient CO₂ Electroreduction in Wide Potential Windows. Acta Physico-Chimica Sinica, 2024, 40(4): 2305026-0. doi: 10.3866/PKU.WHXB202305026
16. [16]
  Wang Wang , Yucheng Liu , Shengli Chen . Use of NiFe Layered Double Hydroxide as Electrocatalyst in Oxygen Evolution Reaction: Catalytic Mechanisms, Electrode Design, and Durability. Acta Physico-Chimica Sinica, 2024, 40(2): 2303059-0. doi: 10.3866/PKU.WHXB202303059
17. [17]
  Shihui Shi , Haoyu Li , Shaojie Han , Yifan Yao , Siqi Liu . Regioselectively Synthesis of Halogenated Arenes via Self-Assembly and Synergistic Catalysis Strategy. University Chemistry, 2024, 39(5): 336-344. doi: 10.3866/PKU.DXHX202312002
18. [18]
  Yunhao Zhang , Yinuo Wang , Siran Wang , Dazhen Xu . Progress in Selective Construction of Functional Aromatics from Nitrogenous Cycloalkanes. University Chemistry, 2024, 39(11): 136-145. doi: 10.3866/PKU.DXHX202401083
19. [19]
  Zhongyan Cao , Youzhi Xu , Menghua Li , Xiao Xiao , Xianqiang Kong , Deyun Qian . Electrochemically Driven Denitrative Borylation and Fluorosulfonylation of Nitroarenes. University Chemistry, 2025, 40(4): 277-281. doi: 10.12461/PKU.DXHX202407017
20. [20]
  Hailian Tang , Siyuan Chen , Qiaoyun Liu , Guoyi Bai , Botao Qiao , Liu Fei . Stabilized Rh/hydroxyapatite Catalyst for Furfuryl Alcohol Hydrogenation: Application of Oxidative Strong Metal-Support Interactions in Reducing Conditions. Acta Physico-Chimica Sinica, 2025, 41(4): 2408004-0. doi: 10.3866/PKU.WHXB202408004

Get Citation

PDF

XML

Metrics

PDF Downloads(14)
Abstract views(1668)
HTML views(277)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142