Citation: Kong Shengnan, Abaid Ullah Malik, Qian Xuefeng, Shu Mouhai, Xiao Wende. C-C Coupling Reactions in Water Catalyzed by Palladium[J]. Chinese Journal of Organic Chemistry, ;2018, 38(2): 432-442. doi: 10.6023/cjoc201709016 shu

C-C Coupling Reactions in Water Catalyzed by Palladium

School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, Shanghai 200240

Corresponding author: Shu Mouhai, mhshu@sjtu.edu.cn
Received Date: 9 September 2017
Revised Date: 18 October 2017
Available Online: 3 March 2017
Fund Project: Project supported by the National Natural Science Foundation of China (No. 21271129)the National Natural Science Foundation of China 21271129

Figures(6)

A microporous organic polymer bearing 2, 2'-bipyridine functional group (MOP-bipy), has been synthesized. After treating with Pd (CH₃CN)₂Cl₂, a composite material Pd/MOP-bipy was obtained. The materials have been characterized by ¹³C CP/MAS NMR, FT-IR, PXRD, SEM, TEM, nitrogen adsorption and thermogravimetric (TG) techniques. The content and valence of palladium in Pd/MOP-bipy have been determined by ICP and XPS. The composite material Pd/MOP-bipy exhibits excellent catalytic activity for Suzuki-Miyaura reaction in water and Sonogashira coupling reaction in methanol/water. The catalyst can be recycled at least five times without significant loss of the activity.
- microporous organic polymer,
- heterogeneous catalysis,
- palladium,
- Suzuki-Miyaura coupling,
- Sonogashira coupling
1. [1]
  Trilla, M.; Pleixats, R.; Man, M. W. C.; Bied, C.; Moreau, J. J. E. Adv. Synth. Catal. 2010, 350, 577.
2. [2]
  Veerakumar, P.; Velayudham, M.; Lu, K. L.; Rajagopal, S. Appl. Catal. A. 2013, 455, 247. doi: 10.1016/j.apcata.2013.01.021
3. [3]
  Gogoi, A.; Chutia, S. J.; Gogoi, P. K.; Bora, U. Appl. Organomet. Chem. 2014, 28, 839. doi: 10.1002/aoc.v28.11
4. [4]
  Dong, W.; Zhang, L.; Wang, C.; Feng, C.; Shang, N.; Gao, S.; Wang, C. RSC Adv. 2016, 6, 37118. doi: 10.1039/C6RA00378H
5. [5]
  He, Y.; Cai, C. J. Organomet. Chem. 2011, 696, 2689. doi: 10.1016/j.jorganchem.2011.04.012
6. [6]
  Nasrollahzadeh, M.; Khalaj, M.; Ehsani, A. ChemInform 2014, 55, 5298.
7. [7]
  Ghorbani-Choghamarani, A.; Tahmasbi, B.; Moradi, P. Appl. Organomet. Chem. 2016, 30, 422. doi: 10.1002/aoc.v30.6
8. [8]
  Falher, L. L.; Mumtaz, A.; Nina Diogo, A.; Thorimbert, S.; Botuha, C. Eur. J. Org. Chem. 2017, 4, 827.
9. [9]
  Wang, T.; Xu, K.; Liu, L.; Xie, H.; Li, Y.; Zhao, W. X. Transition Met. Chem. 2016, 41, 525. doi: 10.1007/s11243-016-0048-1
10. [10]
  Llevot, A.; Monney, B.; Sehlinger, A.; Behrens, S.; Meier, M. A. R. Chem. Commun. 2017, 53, 5157.
11. [11]
  Pasa, S.; Ocak, Y. S.; Temel, H.; Kilicoglu, T. Inorg. Chim. Acta 2013, 405, 493. doi: 10.1016/j.ica.2013.02.038
12. [12]
  Das, P.; Sarmah, C.; Tairai, A.; Bora, U. Appl. Organomet. Chem. 2011, 25, 283. doi: 10.1002/aoc.1755
13. [13]
  Lundgren, R. J.; Stradiotto, M. Chem. Eur. J. 2012, 18, 9758. doi: 10.1002/chem.v18.32
14. [14]
  Zhang, Y. Q.; Wei, X. W.; Yu, R. Catal. Lett. 2010, 135, 256 doi: 10.1007/s10562-010-0293-4
15. [15]
  Botella, L.; Nájera, C. Angew. Chem., Int. Ed. 2002, 41, 179. doi: 10.1002/1521-3773(20020104)41:1<>1.0.CO;2-5
16. [16]
  Collins, G.; Schmidt, M.; O'Dwyer, C.; Holmes, J. D.; Mcglacken, G. P. Angew. Chem., Int. Ed. 2014, 53, 4142. doi: 10.1002/anie.201400483
17. [17]
  Prechtl, M. H.; Scholten, J. D.; Dupont, J. Molecules 2010, 15, 3441. doi: 10.3390/molecules15053441
18. [18]
  Djakovitch, L.; Koehler, K. J. Am. Chem. Soc. 2001, 123, 5990. doi: 10.1021/ja001087r
19. [19]
  Köhler, K.; Heidenreich, R. G.; Soomro, S. S.; Pröckl, S. S. Adv. Synth. Catal. 2010, 350, 2930.
20. [20]
  Kantam, M. L.; Roy, S.; Roy, M.; Sreedhar, B.; Choudary, B. M. Adv. Synth. Catal. 2005, 347, 2002. doi: 10.1002/(ISSN)1615-4169
21. [21]
  Siamaki, A. R.; Khder, A. E. R. S.; Abdelsayed, V.; El-Shall, M. S.; Gupton, B. F. J. Catal. 2011, 279, 1. doi: 10.1016/j.jcat.2010.12.003
22. [22]
  Ramchandani, R. K.; Uphade, B. S.; Vinod, M. P.; Wakharkar, R. D.; Choudhary, V. R. ChemInform 1998, 29, 2071.
23. [23]
  Wang, Y.; Biradar, A. V.; Duncan, C. T.; Asefa, T. J. Mater. Chem. 2010, 20, 7834. doi: 10.1039/c0jm01093f
24. [24]
  Ren, X. M.; Kong, S. N.; Shu, Q. D.; Shu, M. H. Chin. J. Chem. 2016, 34, 373. doi: 10.1002/cjoc.201500797
25. [25]
  Li, H.; Xu, B.; Liu, X.; He, A. S. C.; Xia, H.; Mu, Y. J. Mater. Chem. A 2013, 1, 14108. doi: 10.1039/c3ta13128a
26. [26]
  You, L. X.; Zhu, W. L.; Wang, S. J.; Xiong, G.; Ding, F.; Ren, B. Y.; Dragutan, I.; Dragutan, V.; Sun, Y. G. Polyhedron 2016, 115, 47. doi: 10.1016/j.poly.2016.04.032
27. [27]
  Han, B. H.; Wang, D. Sci. China Chem. 2017, 6, 997.
28. [28]
  Lu, S.; Jin, Y.; Gu, H.; Zhang, W. Sci. China. Chem. 2017, 60, 999. doi: 10.1007/s11426-017-9078-7
29. [29]
  Gang, W.; Fu, Y. -A.; Guo, J. -N.; Xiang, Z. -H. Acta Chim. Sinica 2015, 73, 557(in Chinese).
30. [30]
  Zhou, B. -L.; Chen, L. Acta Chim. Sinica 2015, 73, 487(in Chinese).
31. [31]
  Li, Q.; Razzaque, S.; Jin, S.; Tan, B. Sci. China. Chem. 2017, 60, 1056. doi: 10.1007/s11426-017-9089-3
32. [32]
  McKeown, N. B. Sci. China Chem. 2017, 60, 1023. doi: 10.1007/s11426-017-9058-x
33. [33]
  Huang, N.; Day, G.; Yang, X.; Drake, H.; Zhou, H. C. Sci. China. Chem. 2017, 60, 1007. doi: 10.1007/s11426-017-9084-7
34. [34]
  Li, Y. -Q.; Ben, T.; Qiu, S. -L. Acta Chim. Sinica 2015, 73, 605(in Chinese).
35. [35]
  Liu, G.; Sheng, J.; Zhao, Y. Sci. China Chem. 2017, 60, 1015.
36. [36]
  Xu, Y.; Zhang, C.; Mu, P.; Mao, N.; Wang, X.; He, Q.; Wang, F.; Jiang, J. X. Sci. China Chem. 2017, 60, 1075. doi: 10.1007/s11426-017-9077-0
37. [37]
  Gu, C.; Huang, N.; Chen, Y.; Zhang, H.; Zhang, S.; Li, F.; Ma, Y.; Jiang, D. Angew. Chem., Int. Ed. 2016, 55, 3049. doi: 10.1002/anie.201510723
38. [38]
  Wang, M.; Guo, L.; Cao, D. Sci. China Chem. 2017, 60, 1090. doi: 10.1007/s11426-017-9026-x
39. [39]
  Fang, Z.; Yang, Y. Adv. Mater. Res. 2013, 621, 27.
40. [40]
  Leadbeater, N. E. Chem. Commun. 2005, 36, 2881.
41. [41]
  Simon, M. O.; Li, C. J. Chem. Soc. Rev. 2012, 41, 1415. doi: 10.1039/C1CS15222J
42. [42]
  Paul, S.; Islam, M. M.; Islam, S. M. RSC Adv. 2015, 5, 42193. doi: 10.1039/C4RA17308B
43. [43]
  Cheng, X.; Li, W.; Nie, R.; Ma, X.; Sang, R.; Guo, L.; Wu, Y. Adv. Synth. Catal. 2017, 359, 454. doi: 10.1002/adsc.201600815
44. [44]
  Zdravkov, A. B.; Khimich, N. N. Russ. J. Org. Chem. 2006, 42, 1200. doi: 10.1134/S1070428006080161
45. [45]
  Zhao, Y.; Li, J.; Li, C.; Yin, K.; Ye, D.; Jia, X. ChemInform 2010, 12, 1370.
46. [46]
  Li, Q.; Zhang, L. M.; Bao, J. J.; Li, H. X.; Xie, J. B.; Lang, J. P. Appl. Organomet. Chem. 2014, 28, 861. doi: 10.1002/aoc.v28.12
47. [47]
  Khatyr, A.; Ziessel, R. J. Org. Chem. 2000, 65, 7814. doi: 10.1021/jo000836k
48. [48]
  Li, B.; Guan, Z.; Yang, X.; Wang, W. D.; Wang, W.; Hussain, I.; Song, K.; Tan, B.; Li, T. J. Mater. Chem. A 2014, 2, 11930. doi: 10.1039/C4TA01081G
49. [49]
  Wang, C. A.; Han, Y. F.; Li, Y. W.; Nie, K.; Cheng, X. L.; Zhang, J. P. RSC Adv. 2016, 6, 34866. doi: 10.1039/C6RA03331H
50. [50]
  Liu, B.; Gong, Z. L; Yao, S. W.; Guo, H. T.; Yuan, H. T.; Zhang, Y. S. Chin. J. Appl. Chem. 1999, 16, 80.
51. [51]
  Kibis, L. S.; Titkov, A. I.; Stadnichenko, A. I.; Koscheev, S. V.; Boronin, A. I. Appl. Surf. Sci. 2009, 255, 9248. doi: 10.1016/j.apsusc.2009.07.011
52. [52]
  Zdravkov, A. V., ; Koptelova, L. A.; Novikov, A. V.; Khimich, N. N. Russ. J. Gen. Chem. 2008, 78, 1938. doi: 10.1134/S1070363208100204
53. [53]
  Grosshenny, V.; Romero, F. M.; Ziessel, R. J. Org. Chem. 1997, 28, 1491.
54. [54]
  Hua, S. K.; Hu, Q. P.; Ren, J.; Zeng, B. B. ChemInform 2013, 44, 518.
55. [55]
  Cívicos, J. F.; Alonso, D. A.; Nájera, C. J. Org. Chem. 2012, 2012, 3670.
56. [56]
  Zim, D.; Gruber, A. S.; Ebeling, G.; Dupont, J.; Monteiro, A. L. ChemInform 2000, 2, 2881.
57. [57]
  Wang, H.; Wang, J.; Qiu, W.; Fan, Y.; Liu, X.; Jie, T. Chin. J. Chem. 2010, 28, 2416. doi: 10.1002/cjoc.v28.12
58. [58]
  Liu, J. B.; Zhou, H. P.; Peng, Y. Y. RSC Adv. 2014, 55, 2872.
59. [59]
  Korenaga, T.; Nitatori, K.; Muraoka, H.; Ogawa, S.; Shimada, K. Org. Lett. 2015, 17, 5500. doi: 10.1021/acs.orglett.5b02887
60. [60]
  Peng, L.; Xu, F.; Suzuma, Y.; Orita, A.; Otera, J. ChemInform 2013, 78, 12802.
61. [61]
  Thankachan, A. P.; Sindhu, K. S.; Krishnan, K. K.; Anilkumar, G. Tetrahedron Lett. 2016, 47, 5525.
62. [62]
  Srinivas Reddy, A.; Laali, K. K. Tetrahedron Lett. 2015, 56, 4807. doi: 10.1016/j.tetlet.2015.06.067
63. [63]
  Vaccaro, L.; Strappaveccia, G.; Marrocchi, A.; Pizzo, F.; Luciani, L.; Bartollini, E. Green Chem. 2015, 17, 1071. doi: 10.1039/C4GC01728E
64. [64]
  Yu, L.; Han, Z.; Ding, Y. Org. Process Res. Dev. 2016, 20, 2124. doi: 10.1021/acs.oprd.6b00322
65. [65]
  Landarani Isfahani, A.; Mohammadpoor-Baltork, I.; Mirkhani, V.; Khosropour, A. R.; Moghadam, M.; Tangestaninejad, S. J. Org. Chem. 2015, 2014, 5603.
66. [66]
  Peng, H.; Chen, Y. Q.; Mao, S. L.; Pi, Y. X.; Chen, Y.; Lian, Z. Y.; Meng, T.; Liu, S. H.; Yu, G. A. Org. Biomol. Chem. 2014, 12, 6944. doi: 10.1039/C4OB00846D
67. [67]
  Chang, F.; Liu, Y. P. Synth. Commum. 2017, 47, 961. doi: 10.1080/00397911.2017.1297457
68. [68]
  Severin, R.; Reimer, J.; Doye, S. J. Org. Chem. 2010, 75, 3518. doi: 10.1021/jo100460v
69. [69]
  Mino, T.; Shirae, Y.; Saito, T.; Sakamoto, M.; Fujita, T. ChemInform 2007, 38, 9499.
70. [70]
  Xu, Y.; Zhao, J.; Tang, X.; Wu, W.; Jiang, H. ChemInform 2014, 45, 2029.
1. [1]
  Rui HUANG , Shengjie LIU , Qingyuan WU , Nanfeng ZHENG . Enhanced selectivity of catalytic hydrogenation of halogenated nitroaromatics by interfacial effects. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 201-212. doi: 10.11862/CJIC.20240356
2. [2]
  Jun Guo , Zhenbang Zhuang , Wanqiang Liu , Gang Huang . "Co-coordination force" assisted rigid-flexible coupling crystalline polymer for high-performance aqueous zinc-organic batteries. Chinese Chemical Letters, 2024, 35(9): 109803-. doi: 10.1016/j.cclet.2024.109803
3. [3]
  Zhao Gu , Yunhui Yang , Song Ye , Congyang Wang . 2,3-Arylacylation of allenes through synergetic catalysis of palladium and N-heterocyclic carbene. Chinese Chemical Letters, 2025, 36(5): 110334-. doi: 10.1016/j.cclet.2024.110334
4. [4]
  Wenjiang LI , Pingli GUAN , Rui YU , Yuansheng CHENG , Xianwen WEI . C₆₀-MoP-C nanoflowers van der Waals heterojunctions and its electrocatalytic hydrogen evolution performance. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 771-781. doi: 10.11862/CJIC.20230289
5. [5]
  Junxin Li , Chao Chen , Yuzhen Dong , Jian Lv , Jun-Mei Peng , Yuan-Ye Jiang , Daoshan Yang . Ligand-promoted reductive coupling between aryl iodides and cyclic sulfonium salts by nickel catalysis. Chinese Chemical Letters, 2024, 35(11): 109732-. doi: 10.1016/j.cclet.2024.109732
6. [6]
  Hao-Cong Li , Ming Zhang , Qiyan Lv , Kai Sun , Xiao-Lan Chen , Lingbo Qu , Bing Yu . Homogeneous catalysis and heterogeneous separation: Ionic liquids as recyclable photocatalysts for hydroacylation of olefins. Chinese Chemical Letters, 2025, 36(2): 110579-. doi: 10.1016/j.cclet.2024.110579
7. [7]
  Xinlong Han , Huiying Zeng , Chao-Jun Li . Trifluoromethylative homo-coupling of carbonyl compounds. Chinese Chemical Letters, 2025, 36(1): 109817-. doi: 10.1016/j.cclet.2024.109817
8. [8]
  Fei Yin , Erli Yang , Xue Ge , Qian Sun , Fan Mo , Guoqiu Wu , Yanfei Shen . Coupling WO₃₋_x dots-encapsulated metal-organic frameworks and template-free branched polymerization for dual signal-amplified electrochemiluminescence biosensing. Chinese Chemical Letters, 2024, 35(4): 108753-. doi: 10.1016/j.cclet.2023.108753
9. [9]
  Qijun Tang , Wenguang Tu , Yong Zhou , Zhigang Zou . High efficiency and selectivity catalyst for photocatalytic oxidative coupling of methane. Chinese Journal of Structural Chemistry, 2023, 42(12): 100170-100170. doi: 10.1016/j.cjsc.2023.100170
10. [10]
  Kongchuan Wu , Dandan Lu , Jianbin Lin , Ting-Bin Wen , Wei Hao , Kai Tan , Hui-Jun Zhang . Elucidating ligand effects in rhodium(Ⅲ)-catalyzed arene–alkene coupling reactions. Chinese Chemical Letters, 2024, 35(5): 108906-. doi: 10.1016/j.cclet.2023.108906
11. [11]
  Shengkai Li , Yuqin Zou , Chen Chen , Shuangyin Wang , Zhao-Qing Liu . Defect engineered electrocatalysts for C–N coupling reactions toward urea synthesis. Chinese Chemical Letters, 2024, 35(8): 109147-. doi: 10.1016/j.cclet.2023.109147
12. [12]
  Xin Huang , Yi Zhao , Wanzhen Liang . Vibronic coupling effect on intersystem crossing rates of TADF emitters. Chinese Journal of Structural Chemistry, 2024, 43(6): 100278-100278. doi: 10.1016/j.cjsc.2024.100278
13. [13]
  Jian Ji , Jie Yan , Honggen Peng . Modulation of dinuclear site by orbital coupling to boost catalytic performance. Chinese Journal of Structural Chemistry, 2024, 43(8): 100360-100360. doi: 10.1016/j.cjsc.2024.100360
14. [14]
  Yuehai Zhi , Chen Gu , Huachao Ji , Kang Chen , Wenqi Gao , Jianmei Chen , Dafeng Yan . The advanced development of innovative photocatalytic coupling strategies for hydrogen production. Chinese Chemical Letters, 2025, 36(1): 110234-. doi: 10.1016/j.cclet.2024.110234
15. [15]
  Hailong He , Wenbing Wang , Wenmin Pang , Chen Zou , Dan Peng . Double stimulus-responsive palladium catalysts for ethylene polymerization and copolymerization. Chinese Chemical Letters, 2024, 35(7): 109534-. doi: 10.1016/j.cclet.2024.109534
16. [16]
  Gongcheng Ma , Qihang Ding , Yuding Zhang , Yue Wang , Jingjing Xiang , Mingle Li , Qi Zhao , Saipeng Huang , Ping Gong , Jong Seung Kim . Palladium-free chemoselective probe for in vivo fluorescence imaging of carbon monoxide. Chinese Chemical Letters, 2024, 35(9): 109293-. doi: 10.1016/j.cclet.2023.109293
17. [17]
  Baokang Geng , Xiang Chu , Li Liu , Lingling Zhang , Shuaishuai Zhang , Xiao Wang , Shuyan Song , Hongjie Zhang . High-efficiency PdNi single-atom alloy catalyst toward cross-coupling reaction. Chinese Chemical Letters, 2024, 35(7): 108924-. doi: 10.1016/j.cclet.2023.108924
18. [18]
  Lang Gao , Cen Zhou , Rui Wang , Feng Lan , Bohang An , Xiaozhou Huang , Xiao Zhang . Unveiling inverse vulcanized polymers as metal-free, visible-light-driven photocatalysts for cross-coupling reactions. Chinese Chemical Letters, 2024, 35(4): 108832-. doi: 10.1016/j.cclet.2023.108832
19. [19]
  Mengli Xu , Zhenmin Xu , Zhenfeng Bian . Achieving Ullmann coupling reaction via photothermal synergy with ultrafine Pd nanoclusters supported on mesoporous TiO2. Chinese Journal of Structural Chemistry, 2024, 43(7): 100305-100305. doi: 10.1016/j.cjsc.2024.100305
20. [20]
  Bowen Wang , Longwu Sun , Qianqian Cao , Xinzhi Li , Jianai Chen , Shizhao Wang , Miaolin Ke , Fener Chen . Cu-catalyzed three-component CSP coupling for the synthesis of trisubstituted allenyl phosphorothioates. Chinese Chemical Letters, 2024, 35(12): 109617-. doi: 10.1016/j.cclet.2024.109617

Get Citation

PDF

XML

Metrics

PDF Downloads(11)
Abstract views(1235)
HTML views(139)

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