Citation: Cheng Huicheng, Lin Jinlong, Zhang Yaofeng, Chen Bing, Wang Min, Cheng Lihua, Ma Jiaoli. Recent Advances in Transition-Metal-Catalyzed Directing Group Assisted Nitration of Inert C-H Bonds[J]. Chinese Journal of Organic Chemistry, ;2019, 39(2): 318-327. doi: 10.6023/cjoc201807002 shu

Recent Advances in Transition-Metal-Catalyzed Directing Group Assisted Nitration of Inert C-H Bonds

Cheng Huicheng ^a,b ,
Lin Jinlong ^a ,
Zhang Yaofeng ^a ,
Chen Bing ^a ,
Wang Min ^a ,
Cheng Lihua ^a,b ,
Ma Jiaoli ^a,b,,

a.
College of Chemcal Engineering, Guangdong University of Petrochemical Technology, Maoming 525000
b.
Guangdong Province Petrochemical Corrosion and Safety Engineering Technology Research and Development Center, Maoming 525000

Corresponding author: Ma Jiaoli, xiaojiaoli.good@163.com
Received Date: 1 July 2018
Revised Date: 29 August 2018
Available Online: 26 February 2018
Fund Project: Project supported by the Maoming City Technology Bureau (No. 917313), the Guangdong University of Petrochemical Technology (Nos. 517152、517136、201711656024)

Figures(6)

Aromatic nitro compounds are of great importance as chemical raw materials and organic synthesis intermediates. Traditional electrophilic nitration is difficult to achieve regioselective nitrification. In recent years, transition-metal-catalyzed C-H bond activation has developed rapidly. Most functional groups can be introduced into specific sites of aromatics through the chelation of transition metals with directing groups. Directing-group assisted C-H nitration, which is catalyzed by palladium, rhodium, ruthenium and other transition-metal, has made important progress due to its less byproducts, good regioselectivity and environmental protection. According to different transition metal catalysts, the research progress on transition-metal-catalyzed directing-group assisted C-H nitration is summarized, and the limitations of the research field and prospects for future develop-ment are presented.
- transition metal-catalyzed,
- inert C-H bonds,
- nitration,
- aromatic nitro compounds
1. [1]
  (a) Ono, N. The Nitro Group in Organic Synthesis, Wiley-VCH, New York, 2001.
  (b) Feuer, H.; Nielson, A. T. Nitro Compounds: Recent Advances in Synthesis and Chemistry, VCH, New York, 1990.
  (c) Olah, G. A.; Malhotra, R.; Narang, S. C. Nitration: Methods and Mechanisms, VCH, Weinheim, 1989.
2. [2]
  White, E. Org. Synth. 1973, 47, 44.
3. [3]
  For review on synthesis of nitro compounds, see: Yan, G.; Yang, M. Org. Biomol. Chem. 2013, 11, 2554.
4. [4]
  Prakash, G. K.; Mathew, T. Angew. Chem., Int. Ed. 2010, 49, 1726. doi: 10.1002/anie.v49:10
5. [5]
6. [6]
  Liu, Y.-K.; Lou, S.-J.; Xu, D.-Q.; Xu, Z.-Y. Chem.-Eur. J. 2010, 16, 13590. doi: 10.1002/chem.v16.46
7. [7]
  Zhang, W.; Lou, S.; Liu, Y.; Xu, Z. J. Org. Chem. 2013, 78, 5932. doi: 10.1021/jo400594j
8. [8]
  Zhang, W.; Wu, D.; Zhang, J.; Liu, Y. Eur. J. Org. Chem. 2014, 26, 5827.
9. [9]
  Zhang, W.; Zhang, J.; Ren, S.; Liu, Y. J. Org. Chem. 2014, 79, 11508. doi: 10.1021/jo502145v
10. [10]
  Zhang J.; Zhang, W.; Ren, S.; Cui, J.; Liu, Y. Chin. J. Org. Chem. 2015, 35, 647. doi: 10.6023/cjoc201410042
11. [11]
  Dong, J.; Jin, B.; Sun, P. Org. Lett. 2014, 16, 4540. doi: 10.1021/ol502090n
12. [12]
  Majhi, B.; Kundu, D.; Ahammed, S.; Ranu, B. C. Chem.-Eur. J. 2014, 20, 9862. doi: 10.1002/chem.201403325
13. [13]
  Liang, Y.-F.; Li, X.; Wang, X. C.; Yan, Y.; Feng, P.; Jiao, N. ACS Catal. 2015, 5, 1956. doi: 10.1021/cs502126n
14. [14]
  Zhang, W.; Ren, S.; Zhang, J.; Liu, Y. J. Org. Chem. 2015, 80, 5973. doi: 10.1021/acs.joc.5b00735
15. [15]
  Qiao, H.-J.; Yang, F.; Wang, S.-W.; Leng, Y.-T.; Wu, Y.-J. Tetrahedron 2015, 71, 9258. doi: 10.1016/j.tet.2015.10.035
16. [16]
  Lu, Y.; Li, Y.; Zhang, R.; Jin, K.; Duan, C. Tetrahedron 2013, 69, 9422. doi: 10.1016/j.tet.2013.08.076
17. [17]
  Feng, Y. S.; Mao, L.; Bu, X. S.; Dai, J. J.; Xu, H. J. Tetrahedron 2015, 71, 3827. doi: 10.1016/j.tet.2015.04.013
18. [18]
  Pawar, G. G.; Brahmanandan, A.; Kapur, M. Org. Lett. 2016, 18, 448. doi: 10.1021/acs.orglett.5b03493
19. [19]
  Zhao, F.; Chen, Z.; Huang, S. J.; Jiang, Y. B. Synthesis 2016, 48, 2105. doi: 10.1055/s-00000084
20. [20]
  Chang, M.; Chen, H.; Wang, H. J. Org. Chem. 2017, 82, 10601. doi: 10.1021/acs.joc.7b02311
21. [21]
  Zhang, L.; Liu, Z.; Li, H.; Fang, G.; Barry, B.-D.; Belay, T. A.; Bi, X.; Liu, Q. Org. Lett. 2011, 13, 6536. doi: 10.1021/ol2028288
22. [22]
  Zhang, H.; Zhao, L.; Wang, D. Org. Lett. 2013, 15, 3836. doi: 10.1021/ol401453f
23. [23]
  Katayev, D.; Pfister, K. F.; Wendling, T.; Gool en, L. J. Chem.-Eur. J. 2014, 20, 9902. doi: 10.1002/chem.201403363
24. [24]
  Liu, J.; Zhuang, S.; Gui, Q.; Chen, X.; Yang, Z.; Tan, Z. Adv. Synth. Catal. 2015, 357, 732. doi: 10.1002/adsc.v357.4
25. [25]
  Hernando, E.; Rafael, R.; Castillo, R. R; Rodrguez, N. Chem.-Eur. J. 2014, 20, 13854. doi: 10.1002/chem.v20.43
26. [26]
  Sadhu, P.; Alla, S. K.; Punniyamurthy, T. J. Org. Chem. 2015, 80, 8245. doi: 10.1021/acs.joc.5b01021
27. [27]
  Ji, Y.-F.; Yan, H.; Jiang, Q.-B. Eur. J. Org. Chem. 2015, 2051.
28. [28]
  He, Y.; Zhao, N.; Qiu, L.; Zhang, X.; Fan, X. Org. Lett. 2016, 18, 6054. doi: 10.1021/acs.orglett.6b02998
29. [29]
  Zhu, X.; Qiao, L.; Ye, P.; Ying, B.; Xu, J.; Shen, C.; Zhang, P. RSC Adv. 2016, 6, 89979. doi: 10.1039/C6RA19583K
30. [30]
  Planas, O.; Company, A.; Ribas, X. Adv. Synth. Catal. 2016, 358, 1679. doi: 10.1002/adsc.v358.10
31. [31]
  Khan, B.; Khan, A. A.; Bora, D.; Verma, D.; Koley, D. ChemistrySelect 2017, 2, 260. doi: 10.1002/slct.201601917
32. [32]
  Wang, Y.; Yu, F.; Han, X.; Li, M.; Tong, Y.; Ding, J.; Hou, H. Inorg. Chem. 2017, 56, 5953. doi: 10.1021/acs.inorgchem.7b00653
33. [33]
  Vinayak, B.; Chandrasekharam, M. Org. Lett. 2017, 19, 3528. doi: 10.1021/acs.orglett.7b01489
34. [34]
  Vinayak, B.; Ashok, A.; Chandrasekharam, M. Eur. J. Org. Chem. 2017, 7127.
35. [35]
  Reddy, G. M.; Rao, N. S.; Sarma, M. H. Asian J. Org. Chem. 2017, 6, 59. doi: 10.1002/ajoc.v6.1
36. [36]
  Tu, D.; Luo, J.; Jiang, C. Chem. Commun. 2018, 54, 2514. doi: 10.1039/C8CC00267C
37. [37]
  Wang, C. M.; Tang, K. X.; Gao, T. H.; Chen, L.; Sun, L. P. J. Org. Chem. 2018, 83, 8315. doi: 10.1021/acs.joc.8b01016
38. [38]
  Fan, Z.; Ni, J.; Zhang, A. J. Am. Chem. Soc. 2016, 138, 8470. doi: 10.1021/jacs.6b03402
39. [39]
  Fan, Z.; Li, J.; Lu, H.; Wang, D.-Y.; Wang, C.; Uchiyama, M.; Zhang, A. Org. Lett. 2017, 19, 3199. doi: 10.1021/acs.orglett.7b01297
40. [40]
  Fan, Z.; Lu H.; Zhang, A. J. Org. Chem. 2018, 83, 3245. doi: 10.1021/acs.joc.8b00149
41. [41]
  Xie, F.; Qi, Z. S.; Li, X. W. Angew. Chem., Int. Ed. 2013, 52, 11862. doi: 10.1002/anie.v52.45
42. [42]
  Rao, D. N.; Rasheed, S. K.; Raina, G.; Ahmed, Q. N.; Jaladanki, C. K.; Bharatam, P. V.; Das, P. J. Org. Chem. 2017, 82, 7234. doi: 10.1021/acs.joc.7b00808
43. [43]
  Saxena, P.; Kapur, M. Chem. Asian J. 2018, 13, 861. doi: 10.1002/asia.201800036
44. [44]
  Wan, L.; Qiao, K.; Yuan X.; Zheng, M.-W.; Fan, B.-B.; Di, Z. C.; Zhang, D.; Fang, Z.; Gu, K. Adv. Synth. Catal. 2017, 359, 2596 doi: 10.1002/adsc.v359.15
45. [45]
  Botla, V.; Ramana, D. V.; Chiranjeevi, B.; Chandrasekharam, M. ChemistrySelect 2016, 1, 3974. doi: 10.1002/slct.201600906
46. [46]
  Gao, Y.; Mao, Y.; Zhang, B.; Zhan, Y.; Huo, Y. Org. Biomol. Chem. 2018, 16, 3881. doi: 10.1039/C8OB00841H
1. [1]
  Geyang Song , Dong Xue , Gang Li . Recent Advances in Transition Metal-Catalyzed Synthesis of Anilines from Aryl Halides. University Chemistry, 2024, 39(2): 321-329. doi: 10.3866/PKU.DXHX202308030
2. [2]
  Yan Li , Xinze Wang , Xue Yao , Shouyun Yu . 基于激发态手性铜催化的烯烃E→Z异构的动力学拆分——推荐一个本科生综合化学实验. University Chemistry, 2024, 39(5): 1-10. doi: 10.3866/PKU.DXHX202309053
3. [3]
  Chi Li , Jichao Wan , Qiyu Long , Hui Lv , Ying Xiong . N-Heterocyclic Carbene (NHC)-Catalyzed Amidation of Aldehydes with Nitroso Compounds. University Chemistry, 2024, 39(5): 388-395. doi: 10.3866/PKU.DXHX202312016
4. [4]
  Xiaofeng Zhu , Bingbing Xiao , Jiaxin Su , Shuai Wang , Qingran Zhang , Jun Wang . Transition Metal Oxides/Chalcogenides for Electrochemical Oxygen Reduction into Hydrogen Peroxides. Acta Physico-Chimica Sinica, 2024, 40(12): 2407005-. doi: 10.3866/PKU.WHXB202407005
5. [5]
  Yanan Liu , Yufei He , Dianqing Li . Preparation of Highly Dispersed LDHs-based Catalysts and Testing of Nitro Compound Reduction Performance: A Comprehensive Chemical Experiment for Research Transformation. University Chemistry, 2024, 39(8): 306-313. doi: 10.3866/PKU.DXHX202401081
6. [6]
  Lili Jiang , Shaoyu Zheng , Xuejiao Liu , Xiaomin Xie . Copper-Catalyzed Oxidative Coupling Reactions for the Synthesis of Aryl Sulfones: A Fundamental and Exploratory Experiment for Undergraduate Teaching. University Chemistry, 2025, 40(7): 267-276. doi: 10.12461/PKU.DXHX202408004
7. [7]
  Yan Qi , Yueqin Yu , Weisi Guo , Yongjun Liu . 过渡金属参与的有机反应案例教学与实践探索. University Chemistry, 2025, 40(6): 111-117. doi: 10.12461/PKU.DXHX202411021
8. [8]
  Jiaming Xu , Yu Xiang , Weisheng Lin , Zhiwei Miao . Research Progress in the Synthesis of Cyclic Organic Compounds Using Bimetallic Relay Catalytic Strategies. University Chemistry, 2024, 39(3): 239-257. doi: 10.3866/PKU.DXHX202309093
9. [9]
  Jing WU , Puzhen HUI , Huilin ZHENG , Pingchuan YUAN , Chunfei WANG , Hui WANG , Xiaoxia GU . Synthesis, crystal structures, and antitumor activities of transition metal complexes incorporating a naphthol-aldehyde Schiff base ligand. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2422-2428. doi: 10.11862/CJIC.20240278
10. [10]
  Lina Guo , Ruizhe Li , Chuang Sun , Xiaoli Luo , Yiqiu Shi , Hong Yuan , Shuxin Ouyang , Tierui Zhang . 层状双金属氢氧化物的层间阴离子对衍生的Ni-Al₂O₃催化剂光热催化CO₂甲烷化反应的影响. Acta Physico-Chimica Sinica, 2025, 41(1): 2309002-. doi: 10.3866/PKU.WHXB202309002
11. [11]
  Pengzi Wang , Wenjing Xiao , Jiarong Chen . Copper-Catalyzed C―O Bond Formation by Kharasch-Sosnovsky-Type Reaction. University Chemistry, 2025, 40(4): 239-244. doi: 10.12461/PKU.DXHX202406090
12. [12]
  Danqing Wu , Jiajun Liu , Tianyu Li , Dazhen Xu , Zhiwei Miao . Research Progress on the Simultaneous Construction of C—O and C—X Bonds via 1,2-Difunctionalization of Olefins through Radical Pathways. University Chemistry, 2024, 39(11): 146-157. doi: 10.12461/PKU.DXHX202403087
13. [13]
  Guojie Xu , Fang Yu , Yunxia Wang , Meng Sun . Introduction to Metal-Catalyzed β-Carbon Elimination Reaction of Cyclopropenones. University Chemistry, 2024, 39(8): 169-173. doi: 10.3866/PKU.DXHX202401060
14. [14]
  Feng Han , Fuxian Wan , Ying Li , Congcong Zhang , Yuanhong Zhang , Chengxia Miao . Comprehensive Organic Chemistry Experiment: Phosphotungstic Acid-Catalyzed Direct Conversion of Triphenylmethanol for the Synthesis of Oxime Ethers. University Chemistry, 2025, 40(3): 342-348. doi: 10.12461/PKU.DXHX202405181
15. [15]
  Wei-Bin Li , Xiao-Chao Huang , Pei Liu , Jie Kong , Guo-Ping Yang . Recent advances in directing group assisted transition metal catalyzed para-selective C-H functionalization. Chinese Chemical Letters, 2025, 36(6): 110543-. doi: 10.1016/j.cclet.2024.110543
16. [16]
  Wentao Lin , Wenfeng Wang , Yaofeng Yuan , Chunfa Xu . Concerted Nucleophilic Aromatic Substitution Reactions. University Chemistry, 2024, 39(6): 226-230. doi: 10.3866/PKU.DXHX202310095
17. [17]
  Shulei Hu , Yu Zhang , Xiong Xie , Luhan Li , Kaixian Chen , Hong Liu , Jiang Wang . Rh(Ⅲ)-catalyzed late-stage C-H alkenylation and macrolactamization for the synthesis of cyclic peptides with unique Trp(C7)-alkene crosslinks. Chinese Chemical Letters, 2024, 35(8): 109408-. doi: 10.1016/j.cclet.2023.109408
18. [18]
  Jiaxun Wu , Mingde Li , Li Dang . The R eaction of Metal Selenium Complexes with Olefins as a Tutorial Case Study for Analyzing Molecular Orbital Interaction Modes. University Chemistry, 2025, 40(3): 108-115. doi: 10.12461/PKU.DXHX202405098
19. [19]
  Ping ZHANG , Chenchen ZHAO , Xiaoyun CUI , Bing XIE , Yihan LIU , Haiyu LIN , Jiale ZHANG , Yu'nan CHEN . Preparation and adsorption-photocatalytic performance of ZnAl@layered double oxides. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1965-1974. doi: 10.11862/CJIC.20240014
20. [20]
  Yihao Zhao , Jitian Rao , Jie Han . Synthesis and Photochromic Properties of 3,3-Diphenyl-3H-Naphthopyran: Design and Teaching Practice of a Comprehensive Organic Experiment. University Chemistry, 2024, 39(10): 149-155. doi: 10.3866/PKU.DXHX202402050

Get Citation

PDF

XML

Metrics

PDF Downloads(40)
Abstract views(2923)
HTML views(626)

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