Citation: Mu Bing, Li Jingya, Zou Dapeng, Wu Yusheng, Chang Junbiao, Wu Yangjie. Efficient Pd-Catalyzed Direct C-H Bond Arylation of Imidazo-[1, 2-a]pyridines with Aryl Chlorides in Aqueous Medium[J]. Chinese Journal of Organic Chemistry, ;2018, 38(1): 95-102. doi: 10.6023/cjoc201710029 shu

Efficient Pd-Catalyzed Direct C-H Bond Arylation of Imidazo-[1, 2-a]pyridines with Aryl Chlorides in Aqueous Medium

Mu Bing ^a,b ,
Li Jingya ^d ,
Zou Dapeng ^c ,
Wu Yusheng ^c,d,, ,
Chang Junbiao ^a,c,, ,
Wu Yangjie ^c,,

a.
School of Pharmaceutical Sciences, Zhengzhou University, Zhengzhou 450001
b.
College of Chemistry and Chemical Engineering, Zhengzhou Normal University, Zhengzhou 450044
c.
College of Chemistry and Molecular Engineering, Zhengzhou University, Zhengzhou 450001
d.
Tetranov Biopharm, LLC, Zhengzhou 450001

Corresponding author: Wu Yusheng, yusheng.wu@tetranovglobal.com Chang Junbiao, changjunbiao@zzu.edu.cn Wu Yangjie, wyj@zzu.edu.cn
Received Date: 24 October 2017
Revised Date: 27 November 2017
Available Online: 28 January 2017
Fund Project: the National Natural Science Foundation of China 21702191the Scientific and Technological Project of Henan Province 172102210555Project supported by the National Natural Science Foundation of China (No. 21702191), the Scientific and Technological Project of Henan Province (No. 172102210555) and the Postdoctoral Science Foundation of Henan Province (No. 2014003)the Postdoctoral Science Foundation of Henan Province 2014003

Figures(1)

An efficient and practical protocol for palladium-catalyzed direct C—H bond arylation of imidazo[1, 2-a]pyridines with cheap aryl/heteroaryl chlorides has been developed. Various imidazo[1, 2-a]pyridines with electron-neutral, electron-poor, electron-rich, even sterically hindered aryl chlorides and heteroaryl chlorides were successfully applied to the reaction in aqueous medium to achieve the 3-arylimidazo[1, 2-a]pyridines in mostly good to excellent yields, thus representing a signiﬁ-cant advancement in the implementation of the direct C—H bond arylation of imidazo[1, 2-a]pyridines with aryl chlorides.
- C-H bond arylation,
- imidazo[1, 2-a]pyridines,
- 3-arylimidazo[1, 2-a]pyridines,
- aryl/heteroaryl chlorides,
- aqueous medium
1. [1]
  Bagdi, A. K.; Santra, S.; Monir, K.; Hajra, A. Chem. Commun. 2015, 51, 1555. doi: 10.1039/C4CC08495K
2. [2]
  Moraski, G. C.; Markley, L. D.; Hipskind, P. A.; Boshoff, H.; Cho, S.; Franzblau, S. G.; Miller, M. J. ACS Med. Chem. Lett. 2011, 2, 466. doi: 10.1021/ml200036r
3. [3]
  Egner, U.; Gerbling, K. P.; Hoyer, G. A.; Krüger, G.; Wegner, P. Pestic. Sci. 1996, 47, 145. doi: 10.1002/(SICI)1096-9063(199606)47:2<>1.0.CO;2-7
4. [4]
  Bae, J. S. ; Lee, D. W. ; Lee, D. H. ; Jeong, D. S. WO 2007011163, 2007[Chem. Abstr. 2007, 146, 193485].
5. [5]
  El-Sayed, W. M.; Hussin, W. A.; Al-Faiyz, Y. S.; Ismail, M. A. Eur. J. Pharmacol. 2013, 715, 212. doi: 10.1016/j.ejphar.2013.05.018
6. [6]
  Lacerda, R. B.; de Lima, C. K. F.; da Silva, L. L.; Romeiro, N. C.; Miranda, A. L. P.; Barreiro, E. J.; Fraga, C. A. M. Bioorg. Med. Chem. 2009, 17, 74. doi: 10.1016/j.bmc.2008.11.018
7. [7]
  Shukla, N. M.; Salunke, D. B.; Yoo, E.; Mutz, C. A.; Balakrishna, R.; David, S. A. Bioorg. Med. Chem. 2012, 20, 5850. doi: 10.1016/j.bmc.2012.07.052
8. [8]
  Ismail, M. A.; Arafa, R. K.; Wenzler, T.; Brun, R.; Tanious, F. A.; Wilson, W. D.; Boykin, D. W. Bioorg. Med. Chem. 2008, 16, 683. doi: 10.1016/j.bmc.2007.10.042
9. [9]
  Véron, J. B.; Allouchi, H.; Enguehard-Gueiffier, C.; Snoeck, R.; Andrei, G.; De Clercq, E.; Gueiffier, A. Bioorg. Med. Chem. 2008, 16, 9536. doi: 10.1016/j.bmc.2008.09.027
10. [10]
  Kaminski, J. J.; Doweyko, A. M. J. Med. Chem. 1997, 40, 427. doi: 10.1021/jm950700s
11. [11]
  Rival, Y.; Grassy, G.; Taudon, A.; Ecalle, R. Eur. J. Med. Chem. 1991, 26, 13. doi: 10.1016/0223-5234(91)90208-5
12. [12]
  Enguehard-Gueiffier, C.; Musiu, S.; Henry, N.; Véron, J. B.; Mavel, S.; Neyts, J.; Leyssen, P.; Paeshuyse, J.; Gueiffier, A. Eur. J. Med. Chem. 2013, 64, 448. doi: 10.1016/j.ejmech.2013.03.054
13. [13]
  Patel, H. S.; Linn, J. A.; Drewry, D. H.; Hillesheim, D. A.; Zuercher, W. J.; Hoekstra, W. J. Tetrahedron Lett. 2003, 44, 4077. doi: 10.1016/S0040-4039(03)00875-X
14. [14]
  Liu, G. P.; Cong, X. F.; He, J. H.; Luo, S. Z.; Wu, D.; Lan, J. B. J. Chem. Res. 2012, 36, 687. doi: 10.3184/174751912X13499663832261
15. [15]
  Wu, Z. Q.; Pan, Y. Y.; Zhou, X. G. Synthesis 2011, 2255.
16. [16]
  Dixon, L. I.; Carroll, M. A.; Gregson, T. J.; Ellames, G. J.; Harrington, R. W.; Clegg, W. Org. Biomol. Chem. 2013, 11, 5877. doi: 10.1039/c3ob41112e
17. [17]
  Collins, M. R.; Huang, Q.; Ornelas, M. A.; Scales, S. A. Tetrahedron Lett. 2010, 51, 3528. doi: 10.1016/j.tetlet.2010.04.117
18. [18]
  Monir, K.; Bagdi, A. K.; Ghosh, M.; Hajra, A. Org. Lett. 2014, 16, 4630. doi: 10.1021/ol502218u
19. [19]
  Enguehard, C.; Renou, J. L.; Collot, V.; Hervet, M.; Rault, S.; Gueiffier, A. J. Org. Chem. 2000, 65, 6572. doi: 10.1021/jo000698z
20. [20]
  Marhadour, S.; Bazin, M. A.; Marchand, P. Tetrahedron Lett. 2012, 53, 297. doi: 10.1016/j.tetlet.2011.11.015
21. [21]
  Nandi, D.; Jhou, Y. M.; Lee, J. Y.; Kuo, B. C.; Liu, C. Y.; Huang, P. W.; Lee, H. M. J. Org. Chem. 2012, 77, 9384. doi: 10.1021/jo3015837
22. [22]
  Karale, U. B.; Kalari, S.; Shivakumar, J.; Makane, V. B.; Babar, D. A.; Thakare, R. P.; Nagendra Babu, B.; Chopra, S.; Rode, H. B. RSC Adv. 2016, 6, 65095. doi: 10.1039/C6RA12166G
23. [23]
  Mu, B.; Wu, Y. S.; Li, J. Y.; Zou, D. P.; Chang, J. B.; Wu, Y. J. Org. Biomol. Chem. 2016, 14, 246. doi: 10.1039/C5OB02112J
24. [24]
  Lee, J.; Chung, J.; Byun, S. M.; Kim, B. M.; Lee, C. Tetrahedron 2013, 69, 5660. doi: 10.1016/j.tet.2013.04.031
25. [25]
  Fu, H. Y.; Chen, L.; Doucet, H. J. Org. Chem. 2012, 77, 4473. doi: 10.1021/jo300528b
26. [26]
  Nandi, D.; Siwal, S. S.; Mallick, K. ChemistrySelect 2017, 2, 1747. doi: 10.1002/slct.201601837
27. [27]
  Cao, H.; Zhan, H. Y.; Lin, Y. G.; Lin, X. L.; Du, Z. D.; Jiang, H. F. Org. Lett. 2012, 14, 1688. doi: 10.1021/ol300232a
28. [28]
  Kalari, S.; Babar, D. A.; Karale, U. B.; Makane, V. B.; Rode, H. B. Tetrahedron Lett. 2017, 58, 2818. doi: 10.1016/j.tetlet.2017.06.010
29. [29]
  Choy, P. Y.; Luk, K. C.; Wu, Y. N.; So, C. M.; Wang, L. L.; Kwong, F. Y. J. Org. Chem. 2015, 80, 1457. doi: 10.1021/jo502386w
30. [30]
  Cao, H.; Lin, Y. G.; Zhan, H. Y.; Du, Z. D.; Lin, X. L.; Liang, Q. M.; Zhang, H. RSC Adv. 2012, 2, 5972. doi: 10.1039/c2ra20366a
31. [31]
  Liu, Q. X.; He, B. Y.; Qian, P. C.; Shao, L. X. Org. Biomol. Chem. 2017, 15, 1151. doi: 10.1039/C6OB02704K
32. [32]
  Zhao, G. K.; Zhang, K. N.; Wang, L.; Li, J. Y.; Zou, D. P.; Wu, Y. J.; Wu, Y. S. Tetrahedron Lett. 2015, 56, 6700. doi: 10.1016/j.tetlet.2015.10.053
33. [33]
  Ke, C. H.; Kuo, B. C.; Nandi, D.; Lee, H. M. Organometallics 2013, 32, 4775. doi: 10.1021/om4004219
34. [34]
  Frett, B.; McConnell, N.; Smith, C. C.; Wang, Y. X.; Shah, N. P.; Li, H. Y. Eur. J. Med. Chem. 2015, 94, 123. doi: 10.1016/j.ejmech.2015.02.052
35. [35]
  Hiebel, M. A.; Fall, Y.; Scherrmann, M. C.; Berteina-Raboin, S. Eur. J. Org. Chem. 2014, 2014, 4643. doi: 10.1002/ejoc.201402079
36. [36]
  Cooper, K.; Fray, M. J.; Parry, M. J.; Richardson, K.; Steele, J. J. Med. Chem. 1992, 35, 3115. doi: 10.1021/jm00095a005
1. [1]
  Chunhua Ma , Mengjiao Liu , Siyu Ouyang , Zhenwei Cui , Jingjing Bi , Yuqin Jiang , Zhiguo Zhang . Metal-free construction of diverse 1,2,4-triazolo[1,5-a]pyridines on water. Chinese Chemical Letters, 2025, 36(1): 109755-. doi: 10.1016/j.cclet.2024.109755
2. [2]
  Jiao Chen , Zihan Zhang , Guojin Sun , Yudi Cheng , Aihua Wu , Zefan Wang , Wenwen Jiang , Fulin Chen , Xiuying Xie , Jianli Li . Benzo[4,5]imidazo[1,2-a]pyrimidine-based structure-inherent targeting fluorescent sensor for imaging lysosomal viscosity and diagnosis of lysosomal storage disorders. Chinese Chemical Letters, 2024, 35(11): 110050-. doi: 10.1016/j.cclet.2024.110050
3. [3]
  Yi Luo , Lin Dong . Multicomponent remote C(sp²)-H bond addition by Ru catalysis: An efficient access to the alkylarylation of 2H-imidazoles. Chinese Chemical Letters, 2024, 35(10): 109648-. doi: 10.1016/j.cclet.2024.109648
4. [4]
  Peiyan Zhu , Yanyan Yang , Hui Li , Jinhua Wang , Shiqing Li . Rh(Ⅲ)‐Catalyzed sequential ring‐retentive/‐opening [4 + 2] annulations of 2H‐imidazoles towards full‐color emissive imidazo[5,1‐a]isoquinolinium salts and AIE‐active non‐symmetric 1,1′‐biisoquinolines. Chinese Chemical Letters, 2024, 35(10): 109533-. doi: 10.1016/j.cclet.2024.109533
5. [5]
  Xiangyang Ji , Yishuang Chen , Peng Zhang , Shaojia Song , Jian Liu , Weiyu Song . Boosting the first C–H bond activation of propane on rod-like V/CeO₂ catalyst by photo-assisted thermal catalysis. Chinese Chemical Letters, 2025, 36(5): 110719-. doi: 10.1016/j.cclet.2024.110719
6. [6]
  Haoran Shi , Jiaxin Wang , Yuqin Zhu , Hongyang Li , Guodong Ju , Lanlan Zhang , Chao Wang . Highly selective α-C(sp³)-H arylation of alkenyl amides via nickel chain-walking catalysis. Chinese Chemical Letters, 2024, 35(7): 109333-. doi: 10.1016/j.cclet.2023.109333
7. [7]
  Yu Xiong , Li-Jun Hu , Jian-Guo Song , Di Zhang , Yi-Shuang Peng , Xiao-Jun Huang , Jian Hong , Bin Zhu , Wen-Cai Ye , Ying Wang . Structure elucidation of plumerubradins A–C: Correlations between ¹H NMR signal patterns and structural information of [2+2]-type cyclobutane derivatives. Chinese Chemical Letters, 2025, 36(5): 110149-. doi: 10.1016/j.cclet.2024.110149
8. [8]
  Rong-Nan Yi , Wei-Min He . Photocatalytic Minisci-type multicomponent reaction for the synthesis of 1-(halo)alkyl-3-heteroaryl bicyclo[1.1.1]pentanes. Chinese Chemical Letters, 2024, 35(10): 110115-. doi: 10.1016/j.cclet.2024.110115
9. [9]
  Yunkang Tong , Haiqiao Huang , Haolan Li , Mingle Li , Wen Sun , Jianjun Du , Jiangli Fan , Lei Wang , Bin Liu , Xiaoqiang Chen , Xiaojun Peng . Cooperative bond scission by HRP/H₂O₂ for targeted prodrug activation. Chinese Chemical Letters, 2024, 35(12): 109663-. doi: 10.1016/j.cclet.2024.109663
10. [10]
  Yang Li , Yanan Dong , Zhihong Wei , Changzeng Yan , Zhen Li , Lin He , Yuehui Li . Fluoride-promoted Ni-catalyzed cyanation of C–O bond using CO₂ and NH₃. Chinese Chemical Letters, 2025, 36(5): 110206-. doi: 10.1016/j.cclet.2024.110206
11. [11]
  Tong Li , Leping Pan , Yan Zhang , Jihu Su , Kai Li , Kuiliang Li , Hu Chen , Qi Sun , Zhiyong Wang . Electrochemical construction of 2,5-diaryloxazoles via N–H and C(sp³)-H functionalization. Chinese Chemical Letters, 2024, 35(4): 108897-. doi: 10.1016/j.cclet.2023.108897
12. [12]
  Wen-Tao Ouyang , Jun Jiang , Yan-Fang Jiang , Ting Li , Yuan-Yuan Liu , Hong-Tao Ji , Li-Juan Ou , Wei-Min He . Sono-photocatalytic amination of quinoxalin-2(1H)-ones with aliphatic amines. Chinese Chemical Letters, 2024, 35(10): 110038-. doi: 10.1016/j.cclet.2024.110038
13. [13]
  Qin Cheng , Ming Huang , Qingqing Ye , Bangwei Deng , Fan Dong . Indium-based electrocatalysts for CO₂ reduction to C1 products. Chinese Chemical Letters, 2024, 35(6): 109112-. doi: 10.1016/j.cclet.2023.109112
14. [14]
  Li Li , Zhi-Xin Yan , Chuan-Kun Ran , Yi Liu , Shuo Zhang , Tian-Yu Gao , Long-Fei Dai , Li-Li Liao , Jian-Heng Ye , Da-Gang Yu . Electro-reductive carboxylation of CCl bonds in unactivated alkyl chlorides and polyvinyl chloride with CO₂. Chinese Chemical Letters, 2024, 35(12): 110104-. doi: 10.1016/j.cclet.2024.110104
15. [15]
  Peng Wang , Jianjun Wang , Ni Song , Xin Zhou , Ming Li . Radical dehydroxymethylative fluorination of aliphatic primary alcohols and diverse functionalization of α-fluoroimides via BF₃·OEt₂-catalyzed C‒F bond activation. Chinese Chemical Letters, 2025, 36(1): 109748-. doi: 10.1016/j.cclet.2024.109748
16. [16]
  Ke-Ai Zhou , Lian Huang , Xing-Ping Fu , Li-Ling Zhang , Yu-Ling Wang , Qing-Yan Liu . Fluorinated metal-organic framework for methane purification from a ternary CH4/C2H6/C3H8 mixture. Chinese Journal of Structural Chemistry, 2023, 42(11): 100172-100172. doi: 10.1016/j.cjsc.2023.100172
17. [17]
  Li Li , Xue Ke , Shan Wang , Zhuo Jiang , Yuzheng Guo , Chunguang Kuai . Antioxidative strategies of 2D MXenes in aqueous energy storage system. Chinese Chemical Letters, 2025, 36(5): 110423-. doi: 10.1016/j.cclet.2024.110423
18. [18]
  Dong-Xue Jiao , Hui-Li Zhang , Chao He , Si-Yu Chen , Ke Wang , Xiao-Han Zhang , Li Wei , Qi Wei . Layered (C5H6ON)2[Sb2O(C2O4)3] with a large birefringence derived from the uniform arrangement of π-conjugated units. Chinese Journal of Structural Chemistry, 2024, 43(6): 100304-100304. doi: 10.1016/j.cjsc.2024.100304
19. [19]
  Huakang Zong , Xinyue Li , Yanlin Zhang , Faxun Wang , Xingxing Yu , Guotao Duan , Yuanyuan Luo . Pt/Ti₃C₂ electrode material used for H₂S sensor with low detection limit and high stability. Chinese Chemical Letters, 2025, 36(5): 110195-. doi: 10.1016/j.cclet.2024.110195
20. [20]
  Xiao-Ming Chen , Lianhui Song , Jun Pan , Fei Zeng , Yi Xie , Wei Wei , Dong Yi . Visible-light-induced four-component difunctionalization of alkenes to construct phosphorodithioate-containing quinoxalin-2(1H)-ones. Chinese Chemical Letters, 2024, 35(11): 110112-. doi: 10.1016/j.cclet.2024.110112

Get Citation

PDF

XML

Metrics

PDF Downloads(11)
Abstract views(2817)
HTML views(106)

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