Citation: Zhang Qiang, Li Jihang, Zhao Xin. Magnetic Nanoparticle Supported Imino-pyridine Palladium Catalyzed Suzuki Reactions[J]. Chinese Journal of Organic Chemistry, ;2015, 36(1): 130-136. doi: 10.6023/cjoc201507013 shu

Magnetic Nanoparticle Supported Imino-pyridine Palladium Catalyzed Suzuki Reactions

1.
School of Chemistry Biology and Material Engineering, Suzhou University of Science and Technology, Suzhou 215009

Corresponding author: Zhang Qiang, zhangqiang005@gmail.com
Received Date: 16 July 2015
Revised Date: 22 September 2015

Fund Project: the Scientific Research Foundation of Suzhou University of Science and Technology XKQ201417the Natural Science Foundation of Jiangsu Province BK20150282

Figures(5)

A new magnetic nanoparticle supported palladium catalyst was successfully prepared by attaching palladium acetates to imino-pyridine ligand functionalized silica-coated nano-Fe₃O₄. The as-prepared catalyst was characterized by element analysis, FTIR, TEM, XPS and ICP-AES. It was found to be an efficient catalyst for Suzuki reactions in aqueous medium. And the reactions of various aryl bromides with arylboronic acids could be carried out under air and low Pd loading conditions with 83%～98% yields. Moreover, the catalyst could be easily recovered by magnetic separation and reused five times without a significant loss of catalytic activity.
- magnetic nanoparticle,
- palladium catalyst,
- Suzuki reaction,
- Schiff base
1. [1]
  Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457. doi: 10.1021/cr00039a007
2. [2]
  Corbet, J. P.; Mignani, G. Chem. Rev. 2006, 106, 2651. doi: 10.1021/cr0505268
3. [3]
  Fihri, A.; Bouhrara, M.; Nekoueishahraki, B.; Basset, J.-M.; Polshettiwar, V. Chem. Soc. Rev. 2011, 40, 5181. doi: 10.1039/c1cs15079k
4. [4]
  Tan, J. J.; Chen, Y. G.; Li, H. M.; Yasuda, N. J. Org. Chem. 2014, 79, 8871. doi: 10.1021/jo501326r
5. [5]
  Martin, R.; Buchwald, S. L. Acc. Chem. Res. 2008, 41, 1461. doi: 10.1021/ar800036s
6. [6]
  Fu, G. C. Acc. Chem. Res. 2008, 41, 1555. doi: 10.1021/ar800148f
7. [7]
  Chung, K. H.; So, C. M.; Wong, S. M.; Luk, C. H.; Zhou, Z.; Lau, C. P.; Kwong, F. Y. Chem. Commun. 2012, 48, 1967. doi: 10.1039/c2cc15972d
8. [8]
  Botella, L.; Nájera, C. Angew. Chem., Int. Ed. 2002, 41, 179. doi: 10.1002/1521-3773(20020104)41:1<>1.0.CO;2-5
9. [9]
  Alacid, E.; Nájera, C. Org. Lett. 2008, 10, 5011. doi: 10.1021/ol802024j
10. [10]
  Zhao, X. M.; Xiao, Z. Q.; Liang, T.; Gao, X.; Hao, X. Q.; Song, M. P. Chin. J. Org. Chem. 2014, 34, 2304 (in Chinese). doi: 10.6023/cjoc201405026
11. [11]
  Tang, Y.; Yang, F. F.; Nie, S. P.; Wang, L.; Luo, Z. B.; Lu, H. F. Chin. J. Org.Chem. 2015, 35, 705 (in Chinese). doi: 10.6023/cjoc201408028
12. [12]
  Valente, C.; Çalimsiz, S.; Hoi, K. H.; Mallik, D.; Sayah, M.; Organ, M. G. Angew. Chem., Int. Ed. 2012, 51, 3314. doi: 10.1002/anie.v51.14
13. [13]
  Bai, L.; Wang, J. X. Adv. Synth. Catal. 2008, 350, 315. doi: 10.1002/(ISSN)1615-4169
14. [14]
  Ogasawara, S.; Kato, S. J. Am. Chem. Soc. 2010, 132, 4608. doi: 10.1021/ja9062053
15. [15]
  Wei, J. F.; Jiao, J.; Feng, J. J.; Lv, J.; Zhang, X. R.; Shi, X. Y.; Chen, Z. G. J. Org.Chem. 2009, 74, 6283. doi: 10.1021/jo900481y
16. [16]
  Chu, W. Y.; Wang, M.; Li, X. M.; Hou, Y. J.; Sun, Z. Z. Chin. J. Org. Chem. 2012, 32, 1666 (in Chinese). doi: 10.6023/cjoc201206029
17. [17]
  Rao, X. F.; Liu, C.; Zhang, Y. X.; Gao, Z. M.; Jin, Z. L. Chin. J. Catal. 2014, 35, 357 (in Chinese). doi: 10.1016/S1872-2067(12)60754-2
18. [18]
  Zhang, C. Y.; Shi, R. B.; Chen, C. Y.; Jin, C. M. Chin. J. Org.Chem. 2013, 33, 611 (in Chinese). doi: 10.6023/cjoc201211002
19. [19]
  Gawande, M. B.; Branco, P. S.; Varma, R. S. Chem. Soc. Rev. 2013, 42, 3371. doi: 10.1039/c3cs35480f
20. [20]
  Polshettiwar, V.; Luque, R.; Fihri, A.; Zhu, H. B.; Bouhrara, M.; Basset, J. M. Chem. Rev. 2011, 111, 3036. doi: 10.1021/cr100230z
21. [21]
  Feng, C. L.; Liu, J. P.; Gui, J. Z.; Liu, L. T. Chin. J. Appl. Chem. 2015, 32, 19 (in Chinese).
22. [22]
  Wang, Z.; Yu, Y.; Zhang, Y. X.; Li, S. Z.; Qian, H.; Lin, Z. Y. Green Chem. 2015, 17, 413. doi: 10.1039/C4GC00574K
23. [23]
  Li, P. H.; Wang, L.; Zhang, L.; Wang, G. W. Adv. Synth. Catal. 2012, 354, 1307. doi: 10.1002/adsc.201100725
24. [24]
  Du, Q. W.; Zhang, W.; Ma, H.; Zheng, J.; Zhou, B.; Li, Y. Tetrahedron 2012, 68, 3577. doi: 10.1016/j.tet.2012.03.008
25. [25]
  Beletskaya, I. P.; Cheprakov, A. V. Chem. Rev. 2000, 100, 3009. doi: 10.1021/cr9903048
26. [26]
  Wang, Y.; Wu, Z.; Wang, L.; Li, Z. K.; Zhou, X. G. Chem. Eur. J. 2009, 15, 8971. doi: 10.1002/chem.v15:36
27. [27]
  Lu, Y.; Shi, D. H.; You, Z. L.; Zhou, X. S.; Li, K. J. Coord. Chem. 2012, 65, 339. doi: 10.1080/00958972.2011.653785
28. [28]
  Dawood, K. M.; Kirschning, A. Tetrahedron 2005, 61, 12121. doi: 10.1016/j.tet.2005.07.113
29. [29]
  Phan, N. T. S.; Styring, P. Green Chem. 2008, 10, 1055. doi: 10.1039/b805290e
30. [30]
  Dhara, K.; Sarkar, K.; Srimani, D.; Saha, S. K.; Chattopadhyay, P.; Bhaumik, A. Dalton Trans. 2010, 39, 6395. doi: 10.1039/c003142a
31. [31]
  Jin, X. D.; Zhang, K. Y.; Sun, J.; Wang, J.; Dong, Z. P.; Li, R. Catal. Commun. 2012, 26, 199. doi: 10.1016/j.catcom.2012.05.026
32. [32]
  Quali, A.; Laurent, R.; Caminade, A. M.; Majoral, J.-P.; Tailefer, M. J. Am. Chem. Soc. 2006, 128, 15990. doi: 10.1021/ja066505s
33. [33]
  Quali, A.; Spindler, J. F.; Jutand, A.; Tailefer, M. Adv. Synth. Catal. 2007, 349, 1906. doi: 10.1002/(ISSN)1615-4169
34. [34]
  Cloete, J.; Mapolie, S. F. J. Mol. Catal. A: Chem. 2006, 243, 221. doi: 10.1016/j.molcata.2005.08.002
35. [35]
  Song, J.; Shen, Q.; Xu, F.; Lu, X. Tetrahedron 2007, 63, 5148. doi: 10.1016/j.tet.2007.04.006
36. [36]
  Trilla, M.; Pleixats, R.; Man, M. W. C.; Bied, C.; Moreau, J. E. Adv. Synth. Catal. 2008, 350, 577. doi: 10.1002/adsc.v350:4
37. [37]
  Zhang, Q.; Su, H.; Luo, J.; Wei Y. Y. Green Chem. 2012, 14, 201. doi: 10.1039/C1GC16031A
38. [38]
  Demir, A. S.; Findik, H.; Saygili, N.; Subasi, N. T. Tetrahedron. 2010, 66, 1308. doi: 10.1016/j.tet.2009.12.018
39. [39]
  Schweizer, S.; Becht, J. -M.; Le Drian, C. Org. Lett. 2007, 9, 3777. doi: 10.1021/ol701460z
40. [40]
  Lipshutz, B. H.; Nihan, D. M.; Vinogradova, E.; Taft, B. R.; Boskovic, Z. V. Org. Lett. 2008, 10, 4279. doi: 10.1021/ol801676u
41. [41]
  Chung, J. W.; You, Y.; Huh, H. S.; An, B.-K.; Yoon, S.-J.; Kim, S. H.; Lee, S. W.; Park, S. Y. J. Am. Chem. Soc. 2009, 131, 8163. doi: 10.1021/ja900803d
42. [42]
  Qin, C. X.; Lu, W. J. J. Org. Chem. 2008, 73, 7424. doi: 10.1021/jo801345b
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1.
沈阳化工大学材料科学与工程学院沈阳 110142