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.
1. [1]
  Chi Li , Jichao Wan , Qiyu Long , Hui Lv , Ying Xiong . N-Heterocyclic Carbene (NHC)-Catalyzed Amidation of Aldehydes with Nitroso Compounds. University Chemistry, 2024, 39(5): 388-395. doi: 10.3866/PKU.DXHX202312016
2. [2]
  Qiang Zhang , Yuanbiao Huang , Rong Cao . Imidazolium-Based Materials for CO₂ Electroreduction. Acta Physico-Chimica Sinica, 2024, 40(4): 2306040-0. doi: 10.3866/PKU.WHXB202306040
3. [3]
  Ran Yu , Chen Hu , Ruili Guo , Ruonan Liu , Lixing Xia , Cenyu Yang , Jianglan Shui . Catalytic Effect of H₃PW₁₂O₄₀ on Hydrogen Storage of MgH₂. Acta Physico-Chimica Sinica, 2025, 41(1): 100001-0. doi: 10.3866/PKU.WHXB202308032
4. [4]
  Xiaogang Liu , Mengyu Chen , Yanyan Li , Xiantao Ma . Experimental Reform in Applied Chemistry for Cultivating Innovative Competence: A Case Study of Catalytic Hydrogen Production from Liquid Formaldehyde Reforming at Room Temperature. University Chemistry, 2025, 40(7): 300-307. doi: 10.12461/PKU.DXHX202408007
5. [5]
  Hong RAO , Yang HU , Yicong MA , Chunxin LÜ , Wei ZHONG , Lihua DU . Synthesis and in vitro anticancer activity of phenanthroline-functionalized nitrogen heterocyclic carbene homo- and heterobimetallic silver/gold complexes. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2429-2437. doi: 10.11862/CJIC.20240275
6. [6]
  Yan Qi , Yueqin Yu , Weisi Guo , Yongjun Liu . 过渡金属参与的有机反应案例教学与实践探索. University Chemistry, 2025, 40(6): 111-117. doi: 10.12461/PKU.DXHX202411021
7. [7]
  Shiyan Cheng , Yonghong Ruan , Lei Gong , Yumei Lin . Research Advances in Friedel-Crafts Alkylation Reaction. University Chemistry, 2024, 39(10): 408-415. doi: 10.12461/PKU.DXHX202403024
8. [8]
  Zelong LIANG , Shijia QIN , Pengfei GUO , Hang XU , Bin ZHAO . Synthesis and electrocatalytic CO₂ reduction performance of metal-organic framework catalysts loaded with silver particles. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 165-173. doi: 10.11862/CJIC.20240409
9. [9]
  Xuejie Wang , Guoqing Cui , Congkai Wang , Yang Yang , Guiyuan Jiang , Chunming Xu . Research Progress on Carbon-based Catalysts for Catalytic Dehydrogenation of Liquid Organic Hydrogen Carriers. Acta Physico-Chimica Sinica, 2025, 41(5): 100044-0. doi: 10.1016/j.actphy.2024.100044
10. [10]
  Jiajie Li , Xiaocong Ma , Jufang Zheng , Qiang Wan , Xiaoshun Zhou , Yahao Wang . Recent Advances in In-Situ Raman Spectroscopy for Investigating Electrocatalytic Organic Reaction Mechanisms. University Chemistry, 2025, 40(4): 261-276. doi: 10.12461/PKU.DXHX202406117
11. [11]
  Jingping Li , Suding Yan , Jiaxi Wu , Qiang Cheng , Kai Wang . Improving hydrogen peroxide photosynthesis over inorganic/organic S-scheme photocatalyst with LiFePO₄. Acta Physico-Chimica Sinica, 2025, 41(9): 100104-0. doi: 10.1016/j.actphy.2025.100104
12. [12]
  Lewang Yuan , Yaoyao Peng , Zong-Jie Guan , Yu Fang . Insights into the development of 2D covalent organic frameworks as photocatalysts in organic synthesis. Acta Physico-Chimica Sinica, 2025, 41(8): 100086-0. doi: 10.1016/j.actphy.2025.100086
13. [13]
  Dan Liu . 可见光-有机小分子协同催化的不对称自由基反应研究进展. University Chemistry, 2025, 40(6): 118-128. doi: 10.12461/PKU.DXHX202408101
14. [14]
  Yan Kong , Wei Wei , Lekai Xu , Chen Chen . Electrochemical Synthesis of Organonitrogen Compounds from N-integrated CO₂ Reduction Reaction. Acta Physico-Chimica Sinica, 2024, 40(8): 2307049-0. doi: 10.3866/PKU.WHXB202307049
15. [15]
  Hailang JIA , Hongcheng LI , Pengcheng JI , Yang TENG , Mingyun GUAN . Preparation and performance of N-doped carbon nanotubes composite Co₃O₄ as oxygen reduction reaction electrocatalysts. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 693-700. doi: 10.11862/CJIC.20230402
16. [16]
  Hui-Ying Chen , Hao-Lin Zhu , Pei-Qin Liao , Xiao-Ming Chen . Integration of Ru(Ⅱ)-Bipyridyl and Zinc(Ⅱ)-Porphyrin Moieties in a Metal-Organic Framework for Efficient Overall CO₂ Photoreduction. Acta Physico-Chimica Sinica, 2024, 40(4): 2306046-0. doi: 10.3866/PKU.WHXB202306046
17. [17]
  Wenxiu Yang , Jinfeng Zhang , Quanlong Xu , Yun Yang , Lijie Zhang . Bimetallic AuCu Alloy Decorated Covalent Organic Frameworks for Efficient Photocatalytic Hydrogen Production. Acta Physico-Chimica Sinica, 2024, 40(10): 2312014-0. doi: 10.3866/PKU.WHXB202312014
18. [18]
  Zhanggui DUAN , Yi PEI , Shanshan ZHENG , Zhaoyang WANG , Yongguang WANG , Junjie WANG , Yang HU , Chunxin LÜ , Wei ZHONG . Preparation of UiO-66-NH₂ supported copper catalyst and its catalytic activity on alcohol oxidation. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 496-506. doi: 10.11862/CJIC.20230317
19. [19]
  Shuang Cao , Bo Zhong , Chuanbiao Bie , Bei Cheng , Feiyan Xu . Insights into Photocatalytic Mechanism of H₂ Production Integrated with Organic Transformation over WO₃/Zn_0.5Cd_0.5S S-Scheme Heterojunction. Acta Physico-Chimica Sinica, 2024, 40(5): 2307016-0. doi: 10.3866/PKU.WHXB202307016
20. [20]
  Ke Li , Chuang Liu , Jingping Li , Guohong Wang , Kai Wang . Architecting Inorganic/Organic S-Scheme Heterojunction of Bi₄Ti₃O₁₂ Coupling with g-C₃N₄ for Photocatalytic H₂O₂ Production from Pure Water. Acta Physico-Chimica Sinica, 2024, 40(11): 2403009-0. doi: 10.3866/PKU.WHXB202403009

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(1132)
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