Citation: Yang Youdi, Li Shaopeng, Xie Chao, Liu Hangyu, Wang Yanyan, Mei Qingqing, Liu Huizhen, Han Buxing. Ethylenediamine promoted the hydrogenative coupling of nitroarenes over Ni/C catalyst[J]. Chinese Chemical Letters, ;2019, 30(1): 203-206. doi: 10.1016/j.cclet.2018.04.006 shu

Ethylenediamine promoted the hydrogenative coupling of nitroarenes over Ni/C catalyst

Yang Youdi ^a,b ,
Li Shaopeng ^a,b ,
Xie Chao ^a,b ,
Liu Hangyu ^a,b ,
Wang Yanyan ^a,b ,
Mei Qingqing ^a ,
Liu Huizhen ^a,b,*,, ,
Han Buxing ^a,b,*,,

a.
Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Colloid and Interface and Thermodynamics, CAS Research/Education Center for Excellence in Molecular Sciences, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China
b.
School of Chemistry and Chemical Engineering, University of Chinese Academy of Sciences, Beijing 100049, China

Corresponding author: Liu Huizhen, liuhz@iccas.ac.cn Han Buxing, hanbx@iccas.ac.cn

Received Date: 6 December 2017
Revised Date: 2 April 2018
Accepted Date: 3 April 2018
Available Online: 9 January 2018

Figures(5)

Azobenzene and its derivatives are key raw materials and it is an environmentally friendly method for the preparation of azobenzene by hydrogenative coupling of nitrobenzene. The development of nickel based catalyst for organic transformations is of importance because of its relatively low cost and toxicity. In this work, we found that ethylenediamine can enrich the electron state of Ni and make the azobenzene easily desorb from the surface of the catalyst, which inhibits the hydrogenation of azobenzene to aniline. The selectivity of azobenzene is greatly improved. When the ratio of Ni and ethylenediamine is 1:10, the yield of the azobenzene can reach 95.5%.
- Selective hydrogenation,
- Non-noble metal catalyst,
- Electronic state,
- Azobenzene,
- Organic modifiers
1. [1]
  G.X. Chen, C.F. Xu, X.Q. Huang, et al., Nat. Mater. 15(2016) 564-569. doi: 10.1038/nmat4555
2. [2]
  S. Jones, J. Qu, K. Tedsree, X.Q. Gong, S.C.E. Tsang, Angew. Chem. Int. Ed. 51(2012) 11275-11278. doi: 10.1002/anie.201206035
3. [3]
  I. Cano, A.M. Chapman, A. Urakawa, P.W.N.M. Van Leeuwen, J. Am. Chem. Soc. 136(2014) 2520-2528. doi: 10.1021/ja411202h
4. [4]
  I. Cano, M.A. Huertos, A.M. Chapman, et al., J. Am. Chem. Soc. 137(2015) 7718-7727. doi: 10.1021/jacs.5b02802
5. [5]
  K.R. Kahsar, D.K. Schwartz, J.W. Medlin, J. Am. Chem. Soc.136(136) (2014) 520-526.
6. [6]
  H. Liu, Q. Mei, Y. Wang, H. Liu, B. Han, Sci. China Chem. 59(2016) 1342-1347. doi: 10.1007/s11426-016-0223-0
7. [7]
  J.B. Ernst, S. Muratsugu, F. Wang, M. Tada, F. Glorius, J. Am. Chem. Soc. 138(2016) 10718-10721. doi: 10.1021/jacs.6b03821
8. [8]
  J.B. Ernst, C. Schwermann, G.I. Yokota, et al., J. Am. Chem. Soc. 139(2017) 9144-9147. doi: 10.1021/jacs.7b05112
9. [9]
  A.K. Singh, J. Das, N. Majumdar, J. Am. Chem. Soc. 118(1996) 6185-6191. doi: 10.1021/ja954286x
10. [10]
  L. Hu, X. Cao, L. Chen, et al., Chem. Commun. 48(2012) 3445-3447. doi: 10.1039/c2cc30281k
11. [11]
  X. Liu, H.Q. Li, S. Ye, et al., Angew. Chem. Int. Ed. 53(2014) 7624-7628. doi: 10.1002/anie.201404543
12. [12]
  L. Hu, X. Cao, L. Shi, et al., Org. Lett. 13(2011) 5640-5643. doi: 10.1021/ol202362f
13. [13]
  H. Liu, T. Jiang, B. Han, S. Liang, Y. Zhou, Science 326(2009) 1250-1252. doi: 10.1126/science.1179713
14. [14]
  L.M. Ombaka, P.G. Ndungu, V.O. Nyamori, RSC Adv. 5(2015) 109-122. doi: 10.1039/C4RA12523A
15. [15]
  W. Guo, H. Liu, S. Zhang, et al., Green Chem. 18(2016) 6222-6228. doi: 10.1039/C6GC02630C
1. [1]
  Xin Zhang , Tongxia Jin , Changyin Yang , Dezheng Xu , Haidong Jia , Lin Xu . Azobenzene-containing photoresponsive metal-organic cages. Chinese Chemical Letters, 2025, 36(12): 111135-. doi: 10.1016/j.cclet.2025.111135
2. [2]
  Jinyuan Cui , Tingting Yang , Teng Xu , Jin Lin , Kunlong Liu , Pengxin Liu . Hydrogen spillover enhances the selective hydrogenation of α,β-unsaturated aldehydes on the Cu-O-Ce interface. Chinese Journal of Structural Chemistry, 2025, 44(1): 100438-100438. doi: 10.1016/j.cjsc.2024.100438
3. [3]
  Yinghui Pu , Yiming Niu , Tongtong Gao , Junnan Chen , Bingsen Zhang . Ammonia-directed gas-metal-support interaction forming Ni₃ZnN for efficient hydrogenation. Chinese Chemical Letters, 2026, 37(1): 111520-. doi: 10.1016/j.cclet.2025.111520
4. [4]
  Jiahao Li , Bin Pan , Anruo Mao , Likui Wang , Dawei Wang . Construction of effective and recyclable non-noble metal coordination polymers and their multiple applications in water. Chinese Chemical Letters, 2026, 37(1): 111165-. doi: 10.1016/j.cclet.2025.111165
5. [5]
  Xiaoqian Wang , Yanling Shen , Long Chen , Lizhi Fang , Kuppusamy Kanagaraj , Ming Rao , Chunying Fan , Wanhua Wu , Cheng Yang . Azobenzene-winged phenanthroline for supramolecular chirality sensing and multidimensional chiroptical manipulation via solvent, light, temperature, and redox. Chinese Chemical Letters, 2026, 37(2): 111710-. doi: 10.1016/j.cclet.2025.111710
6. [6]
  Kai Ye , Zhicheng Ye , Chuantao Wang , Zhilai Luo , Cheng Lian , Chunyan Bao . Artificial signal transduction triggered by molecular photoisomerization in lipid membranes. Chinese Chemical Letters, 2025, 36(4): 110033-. doi: 10.1016/j.cclet.2024.110033
7. [7]
  Jiaxuan YANG , Chenfa DENG , Jingyang LIU , Chenzexi XU , Hongxin CHEN , Yahui ZHU , Ying LI , Shuhua WANG , Rongping ZHOU , Chao CHEN . Advances in selective hydrogenation of α, β-unsaturated aldehydes/ketones catalyzed by metal-organic frameworks and their derivatives: A review. Chinese Journal of Inorganic Chemistry, 2025, 41(10): 1973-2010. doi: 10.11862/CJIC.20250175
8. [8]
  Danfeng Zhao , Jing Lin , Rushuo Li , Liang Chu , Zhaokun Wang , Xiubing Huang , Ge Wang . Constructing frustrated Lewis pairs on porous Ce-based metal-organic frameworks with improved dicyclopentadiene hydrogenation activity. Chinese Chemical Letters, 2025, 36(7): 110172-. doi: 10.1016/j.cclet.2024.110172
9. [9]
  Shanqing YANG , Lulu WANG , Qiang ZHANG , Jiajia LI , Yilong LI , Tongliang HU . A propane-selective metal-organic framework for inverse selective adsorption propane/propylene separation. Chinese Journal of Inorganic Chemistry, 2025, 41(10): 2138-2148. doi: 10.11862/CJIC.20250154
10. [10]
  Muhammad Riaz , Rakesh Kumar Gupta , Di Sun , Mohammad Azam , Ping Cui . Selective adsorption of organic dyes and iodine by a two-dimensional cobalt(II) metal-organic framework. Chinese Journal of Structural Chemistry, 2024, 43(12): 100427-100427. doi: 10.1016/j.cjsc.2024.100427
11. [11]
  Min Liu , Di Wang , Zenghui Ye , Donghao Jiang , Bencan Tang , Yanqi Wu , Fengzhi Zhang . Highly stereo- and enantio-selective synthesis of spiro cyclopropyl oxindoles via organic catalyst-mediated cyclopropanation. Chinese Chemical Letters, 2025, 36(10): 110923-. doi: 10.1016/j.cclet.2025.110923
12. [12]
  Ying Li , Yanjun Xu , Xingqi Han , Di Han , Xuesong Wu , Xinlong Wang , Zhongmin Su . A new metal–organic rotaxane framework for enhanced ion conductivity of solid-state electrolyte in lithium-metal batteries. Chinese Chemical Letters, 2024, 35(9): 109189-. doi: 10.1016/j.cclet.2023.109189
13. [13]
  Doudou Liu , Weiwei Guo , Guoliang Mei , Youpeng Dan , Rong Yang , Chao Huang , Yanling Zhai , Xiaoquan Lu . Application of catalyst Cu-t-ZrO₂ based on the electronic metal-support interaction in electrocatalytic nitrate reduction. Chinese Chemical Letters, 2025, 36(8): 110578-. doi: 10.1016/j.cclet.2024.110578
14. [14]
  Yanjie Li , Chaoqun Qu , Siqi Meng , Jiaqi Hu , Ze Gao , Hongji Xu , Rui Gao , Ming Feng . Revealing electronic state evolution of Co(Ⅱ)/Co(Ⅲ) in CoO (111) plane during OER process through magnetic measurement. Chinese Chemical Letters, 2025, 36(3): 109872-. doi: 10.1016/j.cclet.2024.109872
15. [15]
  Hanqing Zhang , Xiaoxia Wang , Chen Chen , Xianfeng Yang , Chungli Dong , Yucheng Huang , Xiaoliang Zhao , Dongjiang Yang . Selective CO2-to-formic acid electrochemical conversion by modulating electronic environment of copper phthalocyanine with defective graphene. Chinese Journal of Structural Chemistry, 2023, 42(10): 100089-100089. doi: 10.1016/j.cjsc.2023.100089
16. [16]
  Hongzhe GUO , Sen WANG , Lu YANG , Fucheng LIU , Jiongpeng ZHAO , Zhaoquan YAO . Highly selective acetylene capture by a pacs-type metal-organic framework constructed using metal-formate complexes as pore partition units. Chinese Journal of Inorganic Chemistry, 2025, 41(10): 2157-2164. doi: 10.11862/CJIC.20250179
17. [17]
  Xiang Wang , Qingping Song , Zixiang He , Gong Zhang , Tengfei Miao , Xiaoxiao Cheng , Wei Zhang . Constructing diverse switchable circularly polarized luminescence via a single azobenzene polymer film. Chinese Chemical Letters, 2025, 36(1): 110047-. doi: 10.1016/j.cclet.2024.110047
18. [18]
  Xinyu Tian , Jiaxiang Guo , Zeyi Li , Shihou Sheng , Tianyu Zhang , Xianfei Li , Chuandong Dou . Control over electronic structures of organic diradicaloids via precise B/O-heterocycle fusion. Chinese Chemical Letters, 2025, 36(1): 110174-. doi: 10.1016/j.cclet.2024.110174
19. [19]
  Jie ZHANG , Xin LIU , Zhixin LI , Yuting PEI , Yuqi YANG , Huimin LI , Zhiqiang LIU . Assembling a luminescence silencing system based on post-synthetic modification strategy: A highly sensitive and selective turn-on metal-organic framework probe for ascorbic acid detection. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 823-833. doi: 10.11862/CJIC.20230310
20. [20]
  Jiabin Zhang , Xiaoke Zhang , Lilei Wang , Lingpeng Yan , Xueli Cheng , Tao Li . Fluorinated fused azobenzene boron-based polymer acceptors with 1000 nm absorbance edges for all-polymer solar cells. Chinese Chemical Letters, 2025, 36(7): 111064-. doi: 10.1016/j.cclet.2025.111064

Get Citation

PDF

XML

Metrics

PDF Downloads(4)
Abstract views(1688)
HTML views(99)

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