Citation: Li Xiaowei, Zhou Jin, Zhuo Shuping. Recent Progress of Supported N-Heterocyclic Carbene Catalyst in Organic Reactions[J]. Chinese Journal of Organic Chemistry, ;2016, 36(7): 1484-1500. doi: 10.6023/cjoc201601022 shu

Recent Progress of Supported N-Heterocyclic Carbene Catalyst in Organic Reactions

Li Xiaowei ^a,b ,
Zhou Jin ^a ,
Zhuo Shuping ^a,*,,

a.
School of Chemical Engineering, Shandong University of Technology, Zibo 255049
b.
State Key Laboratory of Coordination Chemistry, Nanjing University, Nanjing 210023

Corresponding author: Zhuo Shuping, zhuosp_academic@yahoo.com
Received Date: 18 January 2016
Revised Date: 6 March 2016

Fund Project: the National Natural Science Foundation of China Nos. 51502162, 21576159the Open Foundation of State Key Laboratory of Coordination Chemistry of Nanjing University No. SKLCC1613

Figures(1)

The supported N-heterocyclic carbene (NHC) catalysts have been extensively applied in the catalysis of different organic reactions due to its unique characteristic such as high reactivity, easy separation, purification and recyclability. In this paper, the recent progresses in synthesis and application of supported N-heterocyclic carbene metal complexes based on various types of supports, such as polymer, magnetic nanoparticles, carbon and silica material have been reviewed.
- supported catalyst,
- N-heterocyclic carbene,
- organic reactions,
- catalysis
1. [1]
  Öfele, K. J. J. Organomet. Chem. 1968, 12, 42.
2. [2]
  Wanzlick, H. W.; Schönherr, H. J. Angew. Chem., Int. Ed. Engl. 1968, 7, 141.
3. [3]
  Arduengo, A. J.; Harlow, R. L.; Kilne, M. J. Am. Chem. Soc. 1991, 113, 361.
4. [4]
5. [5]
6. [6]
  Yang, H.-Q.; Wang, Y.-W.; Qin, Y.; Chong, Y.-Z.; Yang, Q.-Z.; Li, G.; Zhang, L.; Li, W. Green Chem. 2011, 13, 1352.
7. [7]
  Bru, M.; Dehn, R.; Teles, J. H.; Deuerlein, S.; Danz, M.; Müller, I. B.; Limbach, M. Chem. Eur. J. 2013, 19, 11661.
8. [8]
  Molnár, Á. Chem. Rev. 2011, 111, 2251.
9. [9]
  Ranganath, K. V. S.; Onitsuka, S.; Kumar, A. K.; Inanaga, J. Catal. Sci. Technol. 2013, 3, 2161.
10. [10]
  Schwarz, J.; Böhm, V. P. W.; Gardiner, M. G.; Grosche, M.; Herrmann, W. A.; Hieringer, W.; Raudaschl-Sieber, G. Chem. Eur. J. 2000, 6, 1773.
11. [11]
  Byun, J. W.; Lee, Y.-S. Tetrahedron Lett. 2004, 45, 1837.
12. [12]
  Lee, D. H.; Kim, J. H.; Jun, B. H.; Kang, H.; Park, J.; Lee, Y. S. Org. Lett. 2008, 10, 1609.
13. [13]
  Kim, J. W.; Kim, J. H.; Lee, D. H.; Lee, Y. S. Tetrahedron Lett. 2006, 47, 4745.
14. [14]
  Kim, J. H.; Kim, J. W.; Shokouhimehr, M.; Lee, Y. S. J. Org. Chem. 2005, 70, 6714.
15. [15]
  Kim, J. H.; Lee, D. H.; Jun, B. H.; Lee, Y. S. Tetrahedron Lett. 2007, 48, 7079.
16. [16]
  Steel, P. G.; Teasdale, C. W. T. Tetrahedron Lett. 2004, 45, 8977.
17. [17]
  Yan, C.; Zeng, X.-M.; Zhang, W.-F.; Luo, M.-M. J. Organomet. Chem. 2006, 691, 3391.
18. [18]
  Gil, W.; Boczoń, K.; Trzeciak, A. M.; Ziółkowski, J. J.; Garcia- Verdugo, E.; Luis, S. V.; Sans, V. J. Mol. Catal. A: Chem. 2009, 309, 131.
19. [19]
  Jafarpour, L.; Heck, M. P.; Baylon, C.; Lee, H. M.; Mioskowski, C.; Nolan, S. P. Organometallics 2002, 21, 671.
20. [20]
  Yao, Q.-W.; Zhang, Y.-L. J. Am. Chem. Soc. 2004, 126, 74.
21. [21]
  Mennecke, K.; Grela, K.; Kunz, U.; Kirschning, A. Synlett 2005, 2948.
22. [22]
  Qureshi, Z. S.; Deshmukh, K. M.; Tambade, P. J.; Bhanage, B. M. Synthesis 2011, 243.
23. [23]
  Bagal, D. B.; Watile, R. A.; Khedkar, M. V.; Dhake, K. P.; Bhanage, B. M. Catal. Sci. Technol. 2012, 2, 354.
24. [24]
  Qureshi, Z. S.; Revankar, S. A.; Khedkar, M. V.; Bhanage, B. M. Catal. Today 2012, 198, 148.
25. [25]
  He, Y.; Cai, C. Chem. Commun. 2011, 47, 12319.
26. [26]
  Bergbreiter, D. E.; Su, H. L.; Koizumi, H.; Tian, J.-H. J. Organomet. Chem. 2011, 696, 1272.
27. [27]
  Yu, T.; Li, Y.; Yao, C.-F.; Wu, H.-H.; Liu, Y.-M.; Wu, P. Chin. J. Catal. 2011, 32, 1712.
28. [28]
  Lin, M.-J.; Wang, S.-J.; Zhang, J.-Y.; Luo, W.-J.; Liu, H.-L.; Wang, W.; Su, C.-Y. J. Mol. Catal. A: Chem. 2014, 394, 33.
29. [29]
  Xu, S.-J.; Song, K.-P.; Li, T.; Tan, B. J. Mater. Chem. A 2015, 3, 1272.
30. [30]
  Pahlevanneshan, Z.; Moghadam, M.; Mirkhani, V.; Tangestaninejad, S.; Mohammadpoor-Baltork, I.; Rezaei, S. Appl. Organomet. Chem. 2015, 29, 678.
31. [31]
  Wang, X.-X.; Hu, P.-B.; Xue, F.-J.; Wei, Y.-P. Carbohydr. Polym. 2014, 114, 476.
32. [32]
  Stevens, P. D.; Li, G.-F.; Fan, J.-D.; Yen, M.; Gao, Y. Chem. Commun. 2005, 4435.
33. [33]
  Ranganath, K. V. S.; Schäfer, A. H.; Glorius, F. ChemCatChem 2011, 3, 1889.
34. [34]
  Wittmann, S.; Majoral, J. P.; Grass, R. N.; Stark, W. J.; Reiser, O. Green Process. Synth. 2012, 1, 275.
35. [35]
  Ghotbinejad, M.; Khosropour, A. R.; Mohammadpoor-Baltork, I.; Moghadam, M.; Tangestaninejad, S.; Mirkhani, V. J. Mol. Catal. A: Chem. 2014, 385, 78.
36. [36]
  Zhao, H.-X.; Li, L.-Y.; Wang, J.-Y.; Wang, R.-H. Nanoscale 2015, 7, 3532.
37. [37]
  Wang, Z.; Yu, Y.; Zhang, Y.-X.; Li, S.-Z.; Qian, H.; Lin, Z.-Y. Green Chem. 2015, 17, 413.
38. [38]
  Iglesias, D.; Sabater, S.; Azua, A.; Mata, J. A. New J. Chem. 2015, 39, 6437.
39. [39]
  Shang, N.-Z.; Gao, S.-T.; Feng, C.; Zhang, H.-Y.; Wang, C.; Wang, Z. RSC Adv. 2013, 3, 21863.
40. [40]
  Park, J. H.; Raza, F.; Jeon, S. J.; Kim, H. I.; Kang, T. W.; Yim, D. B.; Kim, J. H. Tetrahedron Lett. 2014, 55, 3426.
41. [41]
  Movaherd, S. K.; Esmatpoursalmani, R.; Bazgir, A. RSC Adv. 2014, 4, 14586.
42. [42]
  Sabater, S.; Mata, J. A.; Peris, E. ACS Catal. 2014, 4, 2038.
43. [43]
  Sabater, S.; Mata, J. A.; Peris, E. Organometallics 2015, 34, 1186.
44. [44]
  Blanco, M.; Álvarez, P.; Blanco, C.; Jiménez, M. V.; Fernández-Tornos, J.; Pérez-Torrente, J. J.; Oro, L. A.; Menéndez, R. Carbon 2015, 83, 21.
45. [45]
  Blanco, M.; Álvarez, P.; Blanco, C.; Jiménez, M. V.; Fernández- Tornos, J.; Pérez-Torrente, J. J.; Oro, L. A.; Menéndez, R. ACS Catal. 2013, 3, 1307.
46. [46]
  Blanco, M.; Álvarez, P.; Blanco, C.; Jiménez, M. V.; Fernández-Tornos, J.; Pérez-Torrente, J. J.; Blasco, j.; Subías, G.; Cuartero, V.; Oro, L. A.; Menéndez, R. Carbon 2016, 96, 66.
47. [47]
  Zhao, Y.-H.; Zhou, Y.-Y.; Ma, D.-D.; Liu, J.-P.; Li, L.; Zhang, T.-Y.; Zhang, H.-B. Org. Biomol. Chem. 2003, 1, 1643.
48. [48]
  Pozo, C. D.; Corma, A.; Iglesias, M.; Sánchez, F. Organometallics 2010, 29, 4491.
49. [49]
  Pozo, C. D.; Corma, A.; Iglesias, M.; Sánchez, F. Green Chem. 2011, 13, 2471.
50. [50]
  Dastgir, S.; Coleman, K. S.; Green, M. L. H. Dalton Trans. 2011, 40, 661.
51. [51]
  Liu, G.; Hou, M.-Q.; Wu, T.-B.; Jiang, T.; Fan, H.-L.; Yang, G.-Y.; Han, B.-X. Phys. Chem. Chem. Phys. 2011, 13, 2062.
52. [52]
  Li, G.; Yang, H.-Q.; Li, W.; Zhang, G.-L. Green Chem. 2011, 13, 2939.
53. [53]
  Lázaro, G.; Fernández-Alvarez, F. J.; Iglesias, M.; Horna, C.; Vispe, E.; Sancho, R.; Lahoz, F. J.; Iglesias, M.; Pérez-Torrente, J. J.; Oro, L. A. Catal. Sci. Technol. 2014, 4, 62.
54. [54]
  Fernández, M.; Ferré, M.; Pla-Quintana, A.; Parella, T.; Pleixats, R.; Roglans, A. Eur. J. Org. Chem. 2014, 6242.
55. [55]
  Rostamnia, S.; Hossieni, H. G.; Doustkhah, E. J. Organomet. Chem. 2015, 791, 18.
56. [56]
  Tyrrell, E.; Whiteman, L.; Williams, N. J. Organomet. Chem. 2011, 696, 3465.
57. [57]
  Borja, G.; Monge-Marcet, A.; Pleixats, R.; Parella, T.; Cattoën, X.; Michel Man, M. W. C. Eur. J. Org. Chem. 2012, 3625.
58. [58]
  Tamami, B.; Farjadian, F.; Ghasemi, S.; Allahyari, H. New J. Chem. 2013, 37, 2011.
59. [59]
  Ghiaci, M.; Zarghani, M.; Khojastehnezhad, A.; Moeinpour, F. RSC Adv. 2014, 4, 15496.
60. [60]
  Conley, M. P.; Copéret, C.; Thieuleux, C. ACS Catal. 2014, 4, 1458.
61. [61]
  Martínez, A.; Krinsky, J. L.; Peñafiel, I.; Castillón, S.; Loponov, K.; Lapkin, A.; Godard, C.; Claver, C. Catal. Sci. Technol. 2015, 5, 310.
62. [62]
  Pahlevanneshan, Z.; Moghadam, M.; Mirkhani, V.; Tangestaninejad, S.; Mohammadpoor-Baltork, I.; Rezaei, S. New. J. Chem. 2015, 39, 9729.
63. [63]
  Romanenko, I.; Gajan, D.; Sayah, R.; Crozet, D.; Jeanneau, E.; Lucas, C.; Leroux, L.; Veyre, L.; Lesage, A.; Emsley, L.; Lacôte, E.; Thieuleux, C. Angew. Chem., Int. Ed. 2015, 54, 1.
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