Citation: Yuan Hang, Chen Huilian, Luo Zhibin, Gao Yuhua, Lu Hongfei. Synthesis of a Pd-Pyridine N-Heterocyclic Carbene Complex (NHC)-PdCl₂(Py) and Its Efficient Application in Coupling Reaction[J]. Chinese Journal of Organic Chemistry, ;2017, 37(11): 2948-2955. doi: 10.6023/cjoc201705027 shu

Synthesis of a Pd-Pyridine N-Heterocyclic Carbene Complex (NHC)-PdCl₂(Py) and Its Efficient Application in Coupling Reaction

Yuan Hang ^a ,
Chen Huilian ^a ,
Luo Zhibin ^b ,
Gao Yuhua ^a,, ,
Lu Hongfei ^a,,

a.
School of Envionmental and Chemical Engineering, Jiangsu University of Science and Technology, Zhenjiang 212003
b.
School of Chemical Engineering, Jiangsu University, Zhenjiang 212003

Corresponding author: Gao Yuhua, Lu Hongfei, zjluhf1979@hotmail.com
Received Date: 17 May 2017
Revised Date: 13 July 2017
Available Online: 11 November 2017
Fund Project: Project supported by the National Natural Science Foundation of China (No. 21402067)the National Natural Science Foundation of China 21402067

Figures(3)

A Pd-pyridine N-heterocyclic carbene complex (NHC)PdCl₂(Py) has been synthesized through two steps and successfully applied as an effective catalyst for the Suzuki coupling reaction, Heck coupling reaction and Sonogashira coupling reaction. The catalyst demonstrates excellent catalytic activity in Suzuki coupling reaction and Sonogashira coupling reaction with a catalyst loading of 0.1 mol% and 1 mol% in Heck coupling reaction.
- carbene,
- suzuki coupling,
- Heck coupling,
- Sonogashira coupling
1. [1]
  Schuster, O.; Yang, L. Y.; Raubenheimer, G. H.; Albrecht, M. Chem. Rev.2009, 109, 3445. doi: 10.1021/cr8005087
2. [2]
  (a) Hahn, F. E.; Jahnke, M. C. Angew. Chem., Int. Ed. 2009, 47, 3122.
  (b) Brien, C. J.; E. Kantchev, A. B.; Hadei, C. V.; Chass, G. A.; .Lough, A.; Hopkinson, A. C.; Organ, M, G. Chem. Eur. J. 2006, 12, 4743.
  (c) Organ, M. G.; Avola, S.; Dubovyk, I.; Hadei, N.; Kantchev, A. B.; C. Brien, J.; Valente, V. Chem. Eur. J.2006, 12, 4749.
  (d) Calimsiz, S.; Sayah, M.; Mallik, D.; Organ, M. G. Angew. Chem., Int. Ed. 2010, 49, 2014.
  (e) Calimsiz, S.; Organ, M. G. Chem. Commun. 2011, 47, 5181.
  (f) Hoi, K. W.; Froese, R. D.; Hopkinson, A. C.; Organ, M. G. Chem. Eur. J. 2012, 18, 145.
3. [3]
  (a) Herrmann, W. A. Angew. Chem., Int. Ed. 2002, 41, 1290.
  (b) Chartoire, A; Frogneux, X.; Boreux, A.; Slawin, A. M. Z.; Nolan, S. P. Organometallics 2012, 31, 6947.
  (c) Farmer, J. L.; Hunter, H. N.; Organ, M. G. J. Am. Chem. Soc. 2012, 134, 17470.
  (d) Sase, S.; Jaric, M.; Metzger, A.; Malakhov, V.; Knochel, P. J. Org. Chem.2008, 73, 7380.
  (e) Colombel, V.; Rombouts, F.; Oehlrich, D.; Molander, G. A. J. Org. Chem. 2012, 77, 2966.
4. [4]
  (a) Kaufhold, O.; Hahn, F. E. Angew. Chem., Int. Ed. 2008, 47, 4507.
  (b) Han, Y.; Huynh, H. V.; Tan, G. K. Organometallics 2007, 26, 6447.
  (c) Liao, C. Y.; Chan, K. T.; Zeng, J. Y.; Hu, C. H.; Tu, C. Y.; Lee, H. M. Organometallics 2007, 26, 1692.
  (d) Zanardi, A.; Mata, J. A.; Peris, E. Organometallics 2009, 28, 4335.
5. [5]
  (a) Arduengo, A. J.; Harlow, R. L.; Kline, M. J. Am. Chem. Soc. 1991, 113, 361.
  (b) Valente, C.; Ho, K. O.; Mallik, D.; Sayah, M.; Organ, M. G. Angew. Chem., Int. Ed. 2012, 51, 3314.
6. [6]
  (a) Lin, Y. C.; Hsueh, H. H.; Kanne, S.; Chang, L. K.; Liu, F. C.; Lee, G. H.; Peng, S. M. Organometallics 2013, 32, 3859.
  (b) Tamami, B.; Farjadian, F.; Ghasemi, S.; Allahyari, H. New J. Chem. 2013, 37, 2011.
  (c) Faraji, L.; Jadidi, K.; Notash, B. Tetrahedron Lett. 2014, 55, 346.
  (d) Wilczewska, A. Z.; Misztalewsk, I. Organometallics 2014, 33, 5203.
  (e) Taira, T.; Yanagimoto, T.; Sakai, K.; Sakai, H.; Endo, A.; Imura, T. Tetrahedron2016, 72, 4117.
7. [7]
  (a) Zhong, R.; Pö thig, A.; Feng, Y. K.; Riener, K.; Herrmann, W. A.; Kühn, F. E. Green Chem.2014, 16, 4955.
  (b)Marion, N.; Nolan, S. P. Acc. Chem. Res. 2008, 41, 1440.
  (c) Xu, S. J.; Song, K. P.; Li, T.; Tan, B. J. Mater. Chem. A 2015, 3, 1272.
  (d) Xu, C.; Li, H. M.; Xiao, Z. Q.; Wang, Z. Q.; Tang, S. F.; Ji, B. M.; Hao, X. Q.; Song, M. P. Dalton Trans. 2014, 43, 10235.
  (e) Rajabi, F.; Thiel, W. R. Adv. Synth. Catal. 2014, 356, 1873.
8. [8]
  (a) Gallop, C. W. D.; Chen, M. T.; Navarro, O. Org. Lett. 2014, 16, 3724.
  (b) Boubakri, L.; Yasar, S.; Dorcet, V.; Roisnel, T.; Bruneau, C.; Hamdib, N.; Ozdemira, I. New J. Chem. 2017, 41, 5105.
  (c) Bernhammer, J. C.; Chong, N. X.; Jothibasu, R.; Zhou, B. B; Huynh, H. V. Organometallics 2014, 33, 3607.
  (d) John, A.; Modak, S.; Madasu, M.; Katari, M.; Ghosh, P. Polyhedron 2013, 64, 20.
9. [9]
  Lu, H. F.; Wang, L.; Yang, F. F.; Wu, R. Z.; Shen, W. RSC Adv. 2014, 4, 30447. doi: 10.1039/C4RA02480J
10. [10]
  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).
11. [11]
  Rajabi, F.; Thiel, W. R. Adv. Synth. Catal. 2014, 356, 1873. doi: 10.1002/adsc.201300841
12. [12]
  Zhou, W. J.; Wang, K. H.; Wang, J. X.; Huang, D. F. Eur. J. Org. Chem. 2010, 416.
13. [13]
  Liu, W.; Tian, F.; Wang, X. L.; Yu, H.; Bi, Y. L. Chem. Commun. 2013, 49, 2983. doi: 10.1039/c3cc40695d
14. [14]
  Long, R. R.; Yan, X. F.; Wu, Z. Q.; Li, Z. K.; Xiang, H. F.; Zhou, X. G. Org. Biomol. Chem. 2015, 13, 3571. doi: 10.1039/C5OB00132C
15. [15]
  Edsall, R. J.; Harris, H. A.; Manas, E. S.; Mewshaw, R. E. Bioorg. Med. Chem. 2003, 11, 3457. doi: 10.1016/S0968-0896(03)00303-1
16. [16]
  So, C. M.; Chow, W. K.; Choy, P. Y.; Lau, C. P.; Kwong, F. Y. Chem. Eur. J. 2010, 16, 7996. doi: 10.1002/chem.201000723
17. [17]
  Perretti, M. D.; Monzon, D. M.; Crisostomo, F. P.; Martn, V. S.; Carrillo, R. Chem. Commun. 2016, 52, 9036. doi: 10.1039/C5CC09911K
18. [18]
  Duan, S. T.; Xu, Y. S.; Zhang, X. Y.; Fan, Y. S. Chem. Commun. 2016, 52, 10529. doi: 10.1039/C6CC04756D
19. [19]
  Zhao, F.; Luo, J. Y.; Tan, Q.; Liao, Y. F.; Peng, S. M.; Deng, G. J. Adv. Synth. Catal. 2012, 354, 1914. doi: 10.1002/adsc.v354.10
20. [20]
  Zhang, Y. G.; Liu, X. L.; He, Y. Z.; Li, X. M.; Kang, H. J.; Tian, S. K. Chem. Eur. J. 2014, 20, 2765. doi: 10.1002/chem.v20.10
21. [21]
  Yu, L.; Huang, Y. P.; Wei, Z.; Ding, Y. H.; Su, C. L.; Xu, Q. J. Org. Chem. 2015, 80, 8677. doi: 10.1021/acs.joc.5b01358
22. [22]
  Hong, F. J.; Low, Y. Y.; Chong, K. W.; Thomas, N. F.; Kam, T. S. J. Org. Chem. 2014, 79, 4528. doi: 10.1021/jo500559r
23. [23]
  Sagadevan, A.; Hwanga, K. C. Adv. Synth. Catal. 2012, 354, 3421. doi: 10.1002/adsc.v354.18
24. [24]
  Zhao, D. B.; Gao, C.; Su, X. Y.; He, Y. Q.; You, J. S.; Xue, Y. Chem. Commun. 2010, 46, 9049. doi: 10.1039/c0cc03772a
25. [25]
  Kim, T.; Jeong, K. H.; Kim, Y.; Noh, T.; Choi, J.; Ham, J. Eur. J. Org. Chem. 2017, 2425.
26. [26]
  Jadhav, S. N.; Kumbhar, A. S.; Mali, S. S.; Hong, C. K.; Salunkhe, R. S. New J. Chem. 2015, 39, 2333. doi: 10.1039/C4NJ02025A
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Synthesis of a Pd-Pyridine N-Heterocyclic Carbene Complex (NHC)-PdCl2(Py) and Its Efficient Application in Coupling Reaction

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Synthesis of a Pd-Pyridine N-Heterocyclic Carbene Complex (NHC)-PdCl₂(Py) and Its Efficient Application in Coupling Reaction