Citation: Zhifeng Dai, Fang Chen, Qi Sun, Yanyan Ji, Liang Wang, Xiangju Meng, Feng-Shou Xiao. A Pd-metalated porous organic polymer as a highly efficient heterogeneous catalyst for C-C couplings[J]. Chinese Journal of Catalysis, ;2016, 37(1): 54-60. doi: 10.1016/S1872-2067(15)60952-4 shu

A Pd-metalated porous organic polymer as a highly efficient heterogeneous catalyst for C-C couplings

1.
Key Laboratory of Applied Chemistry of Zhejiang Province and Department of Chemistry, Zhejiang University, Hangzhou 310028, Zhejiang, China

Corresponding author: Xiangju Meng,
Received Date: 20 May 2015
Available Online: 28 June 2015
Fund Project: 国家自然科学基金(21422306, 21203165, 21403193) (21422306, 21203165, 21403193) 中央高校基本科研业务费专项资金(2015XZZX004-04). (2015XZZX004-04)

An efficient catalyst system based on a Pd-metalated porous organic polymer bearing phenanthroline ligands was designed and synthesized. This catalyst was applied to various C-C bond-forming reactions, including the Suzuki, Heck and Sonogashira couplings, and afforded the corresponding products while exhibiting excellent activities and selectivities. More importantly, this catalyst can be readily recycled. These features show that such catalysts have significant potential applications in the future.
- Porous organic polymer,
- Phenanthroline ligand,
- Carbon-carbon couplings,
- Pd-based heterogeneous catalyst
1. [1]
  [1] F. Diederich, A. de Meijere, Metal-Catalyzed Cross-Coupling Reactions, 2nd ed., Wiley-VCH, Weinheim, 2004, 4.
2. [2]
  [2] L. X. Yin, J. Liebscher, Chem. Rev., 2007, 107, 133.
3. [3]
  [3] N. Miyaura, A. Suzuki, Chem. Rev., 1995, 95, 2457.
4. [4]
  [4] C. M. Wei, C. J. Li, J. Am. Chem. Soc., 2003, 125, 9584.
5. [5]
  [5] J. Magano, J. R. Dunetz, Chem. Rev., 2011, 111, 2177.
6. [6]
  [6] N. E. Leadbeater, M. Marco, Chem. Rev., 2002, 102, 3217.
7. [7]
  [7] W. Watanabe, T. Maekawa, Y. Miyazaki, T. Kida, K. Takeshita, A. Mori, Chem Asian J., 2012, 7, 1679.
8. [8]
  [8] M. Bakherad, A. Keivanloo, S. Samangooei, Chin. J. Catal., 2014, 35, 324.
9. [9]
  [9] C. E. Garrett, K. Prasad, Adv. Synth. Catal., 2004, 346, 889.
10. [10]
  [10] C. J. Welch, J. Albaneze-Walker, W. R. Leonard, M. Biba, J. DaSilva, D. Henderson, B. Laing, D. J. Mathre, S. Spencer, X. D. Bu, T. B. Wang, Org. Process Res. Dev., 2005, 9, 198.
11. [11]
  [11] H. U. Blaser, A. Indolese, A. Schnyder, H. Steiner, M. Studer, J. Mol. Catal. A, 2001, 173, 3.
12. [12]
  [12] B. M. Bhanage, M. Arai, Catal. Rev., 2001, 43, 315.
13. [13]
  [13] X. Jin, V. V. Balasubramanian, S. T. Selvan, D. P. Sawant, M. A. Chari, G. Q. Lu, A. Vinu, Angew. Chem. Int. Ed., 2009, 48, 7884.
14. [14]
  [14] M. Kawaguchi, S. Yagi, H. Enomoto, Carbon, 2004, 42, 345.
15. [15]
  [15] Q. H. Fan, Y. M. Li, A. S. C. Chan, Chem. Rev., 2002, 102, 3385.
16. [16]
  [16] S. Minakata, M. Komatsu, Chem. Rev., 2009, 109, 711.
17. [17]
  [17] D. E. De Vos, M. Dams, B. F. Sels, P. A. Jacobs, Chem. Rev., 2002, 102, 3615.
18. [18]
  [18] A. Taguchi, F. Schuth, Microporous Mesoporous Mater., 2005, 77, 1.
19. [19]
  [19] M. Hartmann, Chem. Mater., 2005, 17, 4577.
20. [20]
  [20] A. Corma, H. Garcia, Adv. Synth. Catal., 2006, 348, 1391.
21. [21]
  [21] A. Thomas, Angew. Chem. Int. Ed., 2010, 49, 8328.
22. [22]
  [22] Q. Sun, M. Jiang, Z. J. Shen, Y. Y. Jin, S. X. Pan, L. Wang, X. J. Meng, W. Z. Chen, Y. J. Ding, J. X. Li, F-S. Xiao, Chem. Commun., 2014, 50, 11844.
23. [23]
  [23] Q. Sun, Z. F. Dai, X. L. Liu, N. Sheng, F. Deng, X. J. Meng, F-S. Xiao, J. Am. Chem. Soc., 2015, 137, 5204.
24. [24]
  [24] Q. Sun, X. J. Meng, X. L. Liu, X. M. Zhang, Y. Yang, Q. H. Yang, F-S. Xiao, Chem. Commun., 2012, 48, 10505.
25. [25]
  [25] Y. Huangfu, Q. Sun, S. X. Pan, X. J. Meng, F-S. Xiao, ACS Catal., 2015, 5, 1556.
26. [26]
  [26] C. Bleschke, J. Schmidt, D. S. Kundu, S. Blechert, A. Thomas, Adv. Synth. Catal., 2011, 353, 3101.
27. [27]
  [27] J. D. Crowley, S. M. Goldup, N. D. Gowans, D. A. Leigh, V. E. Ronaldson, A. M. Z. Slawin, J. Am. Chem. Soc., 2010, 132, 6243.
28. [28]
  [28] T. Hamada, X. Ye, S. S. Stahl, J. Am. Chem. Soc., 2008, 130, 833.
29. [29]
  [29] M. Boltz, A. Blanc, G. Laugel, P. Pale, B. Louis, Chin. J. Catal., 2011, 32, 807.
30. [30]
  [30] J. L. Hu, Y. L. Gu, Z. H. Guan, J. J. Li, W. L. Mo, T. Li, G. X. Li, ChemSusChem, 2011, 4, 1767.
31. [31]
  [31] Y. X. Gao, G. Wang, L. Chen, P. X. Xu, Y. F. Zhao, Y. B. Zhou, L. B. Han, J. Am. Chem. Soc., 2009, 131, 7956.
32. [32]
  [32] Q. Sun, Z. F. Lv, Y. Y. Du, Q. M. Wu, L. Wang, L. F. Zhu, X. J. Meng, W. Z. Chen, F-S. Xiao, Chem. Asian J., 2013, 8, 2822.
33. [33]
  [33] J. P. Lecomte, A. Kirsch-De Mesmaeker, M. Demeunynck, J. Lhomme, J. Chem. Soc., Faraday Trans., 1993, 89, 3261.
34. [34]
  [34] W. H. Lin, W. L. Sun, J. Yang, Q. H. Sun, Z. Q. Shen, J. Phys. Chem. C, 2009, 113, 16884.
35. [35]
  [35] M. B. Majewski, N. R. de Tacconi, F. M. MacDonnell, M. O. Wolf, Inorg. Chem., 2011, 50, 9939.
36. [36]
  [36] X. Y. Liu, Y. L. Hu, B. Y. Wang, Z. X. Su, Synth. Metals, 2009, 159, 1557.
37. [37]
  [37] P. Siemsen, R. C. Livingston, F. Diederich, Angew. Chem. Int. Ed., 2000, 39, 2632
38. [38]
  [38] A. Elangovan, Y. H. Wang, T. I. Ho, Org. Lett., 2003, 5, 1841.
39. [39]
  [39] S. Thorand, N. Krause, J. Org. Chem., 1998, 63, 8551.
40. [40]
  [40] F. J. Liu, L. Wang, Q. Sun, L. F. Zhu, X. J. Meng, F. S. Xiao, J. Am. Chem. Soc., 2012, 134, 16948.
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