Citation: Wang Ao, Xiao Yonglong, Zhou Yu, Xu Jinyi, Liu Hong. Progress of Organic Reactions Catalyzed by N-Heterocyclic Carbenes[J]. Chinese Journal of Organic Chemistry, ;2017, 37(10): 2590-2608. doi: 10.6023/cjoc201702041 shu

Progress of Organic Reactions Catalyzed by N-Heterocyclic Carbenes

Wang Ao ^a,b ,
Xiao Yonglong ^b ,
Zhou Yu ^b,, ,
Xu Jinyi ^a ,
Liu Hong ^b,,

a.
State Key Laboratory of Natural Medicines and Department of Medicinal Chemistry, China Pharmaceutical University, Nanjing 210000
b.
CAS Key Laboratory of Receptor Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203

Corresponding author: Zhou Yu, zhouyu@simm.ac.cn Liu Hong, hliu@simm.ac.cn
Received Date: 26 February 2017
Revised Date: 25 May 2017
Available Online: 2 October 2017
Fund Project: the National Natural Science Foundation of China 21632008Project supported by the National Natural Science Foundation of China (No. 21632008)

Figures(19)

Since the first stable N-heterocyclic carbene was isolated by Arduengo in 1991, N-heterocyclic carbine has developed rapidly as a kind of efficient organic catalyst. It plays important role in building complex molecules in organic synthesis for the characteristics of umpolung. Some special Lewis bases and oxidants can induce carbine reaction with carbonyl to form Breslow intermediates, enol and homoenolate, which expand the reaction greatly. In this paper, the recent progresses in organic catalytic reactions including Stetter reaction, a³-d³ umpolung catalyzed by carbines are reviewed.
- N-heterocyclic carbene,
- organic catalytic,
- umpolung
1. [1]
  Nef, J. U. Justus Liebigs Ann. Chem. 1895, 287, 265. doi: 10.1002/(ISSN)1099-0690
2. [2]
  Lin, J. C. Y.; Huang, R. T. W.; Lee, C. S.; Bhattacharyya, A.; Hwang, W. S.; Lin, I. J. B. Chem. Rev. 2009, 109, 3561. doi: 10.1021/cr8005153
3. [3]
  Garrison, J. C.; Youngs, W. J. Chem. Rev. 2005, 105, 3978. doi: 10.1021/cr050004s
4. [4]
  Peris, E.; Crabtree, R. H. Coord. Chem. Rev. 2004, 248, 2239. doi: 10.1016/j.ccr.2004.04.014
5. [5]
  Ukai, T.; Tanaka, R.; Dokawa, T. J. Pharm. Soc. Jpn. 1943, 63, 296. doi: 10.1248/yakushi1881.63.6_296
6. [6]
  Shapiro, L. R.; Samuels, S.; Breslow, L.; Camacho, T. Am. J. Public Health 1983, 73, 773. doi: 10.2105/AJPH.73.7.773
7. [7]
  Enders, D.; Grossmann, A.; Fronert, J.; Raabe, G. Chem. Commun. 2010, 46, 6282. doi: 10.1039/c0cc02013c
8. [8]
  Thai, K.; Langdon, S. M.; Bilodeau, F.; Gravel, M. Org. Lett. 2013, 15, 2214. doi: 10.1021/ol400769t
9. [9]
  Langdon, S. M.; Wilde, M. M.; Thai, K.; Gravel, M. J. Am. Chem. Soc. 2014, 136, 7539. doi: 10.1021/ja501772m
10. [10]
  Haghshenas, P.; Gravel, M. Org. Lett. 2016, 18, 4518. doi: 10.1021/acs.orglett.6b02123
11. [11]
  Murry, J. A.; Frantz, D. E.; Soheili, A.; Tillyer, R.; Grabowski, E. J. J.; Reider, P. J. J. Am. Chem. Soc. 2001, 123, 9696. doi: 10.1021/ja0165943
12. [12]
  DiRocco, D. A.; Rovis, T. Angew. Chem., Int. Ed. 2012, 51, 5904. doi: 10.1002/anie.201202442
13. [13]
  Sun, L. H.; Liang, Z. Q.; Jia, W. Q.; Ye, S. Angew. Chem., Int. Ed. 2013, 52, 5803. doi: 10.1002/anie.201301304
14. [14]
  Xu, J.; Mou, C.; Zhu, T.; Song, B. A.; Chi, Y. R. Org. Lett. 2014, 16, 3272. doi: 10.1021/ol501286e
15. [15]
  Stetter, H. Angew. Chem., Int. Ed. Engl. 1976, 15.
16. [16]
  Ciganek, E. Synthesis-Stuttgart 1995, 1311.
17. [17]
  Enders, D.; Breuer, K.; Raabe, G.; Runsink, J.; Teles, J. H.; Melder, J. P.; Ebel, K.; Brode, S. Angew. Chem., Int. Ed. Engl. 1995, 34, 1021. doi: 10.1002/(ISSN)1521-3773
18. [18]
  de Alaniz, J. R.; Kerr, M. S.; Moore, J. L.; Rovis, T. J. Org. Chem. 2008, 73, 2033. doi: 10.1021/jo702313f
19. [19]
  Cullen, S. C.; Rovis, T. Org. Lett. 2008, 10, 3141. doi: 10.1021/ol801047k
20. [20]
  Wang, Z.; Yu, Z.; Wang, Y.; Shi, D. Synthesis 2012, 44, 1559. doi: 10.1055/s-0031-1290976
21. [21]
  Law, K. R.; McErlean, C. S. P. Chem.-Eur. J. 2013, 19, 15852. doi: 10.1002/chem.201303435
22. [22]
  Liu, G.; Wilkerson, P. D.; Toth, C. A.; Xu, H. Org. Lett. 2012, 14, 858. doi: 10.1021/ol203375y
23. [23]
  Li, Y.; Shi, F.-Q.; He, Q.-L.; You, S.-L. Org. Lett. 2009, 11, 3182. doi: 10.1021/ol9013238
24. [24]
  Vedachalam, S.; Tan, S. M.; Teo, H. P.; Cai, S.; Liu, X.-W. Org. Lett. 2012, 14, 174. doi: 10.1021/ol202959y
25. [25]
  Bortolini, O.; Fantin, G.; Fogagnolo, M.; Giovannini, P. P.; Massi, A.; Pacifico, S. Org. Biomol. Chem. 2011, 9, 8437. doi: 10.1039/c1ob06480k
26. [26]
  Zhang, J.; Xing, C.; Tiwari, B.; Chi, Y. R. J. Am. Chem. Soc. 2013, 135, 8113. doi: 10.1021/ja401511r
27. [27]
  Fang, X.; Chen, X.; Chi, Y. R. Org. Lett. 2011, 13, 4708. doi: 10.1021/ol201917u
28. [28]
  McCusker, E. O.; Scheidt, K. A. Angew. Chem., Int. Ed. 2013, 52, 13616. doi: 10.1002/anie.201307292
29. [29]
  Xu, J.; Chen, X.; Wang, M.; Zheng, P.; Song, B. A.; Chi, Y. R. Angew. Chem., Int. Ed. 2015, 54, 5161. doi: 10.1002/anie.v54.17
30. [30]
  Zhao, X.; Ruhl, K. E.; Rovis, T. Angew. Chem., Int. Ed. 2012, 51, 12330. doi: 10.1002/anie.v51.49
31. [31]
  Mo, J.; Yang, R.; Chen, X.; Tiwari, B.; Chi, Y. R. Org. Lett. 2013, 15, 50. doi: 10.1021/ol303035r
32. [32]
  Li, F.; Wu, Z.; Wang, J. Angew. Chem., Int. Ed. 2015, 54, 656.
33. [33]
  Xu, J.; Yuan, S.; Peng, J.; Miao, M.; Chen, Z.; Ren, H. Chem. Commun. 2017, 53, 3430. doi: 10.1039/C7CC01232B
34. [34]
  Zhang, H.-M.; Gao, Z.-H.; Ye, S. Org. Lett. 2014, 16, 3079. doi: 10.1021/ol501205v
35. [35]
  Zhao, Y. M.; Cheung, M. S.; Lin, Z.; Sun, J. Angew. Chem., Int. Ed. 2012, 51, 10359. doi: 10.1002/anie.201204521
36. [36]
  Ni, Q.; Zhang, H.; Grossmann, A.; Loh, C. C.; Merkens, C.; Enders, D. Angew. Chem., Int. Ed. 2013, 52, 13562. doi: 10.1002/anie.201305957
37. [37]
  Dong, X.; Yang, W.; Hu, W.; Sun, J. Angew. Chem., Int. Ed. 2015, 54, 660.
38. [38]
  Rong, Z. Q.; Jia, M. Q.; You, S. L. Org. Lett. 2011, 13, 4080. doi: 10.1021/ol201595f
39. [39]
  Yao, C.; Wang, D.; Lu, J.; Li, T.; Jiao, W.; Yu, C. Chemistry 2012, 18, 1914. doi: 10.1002/chem.201103358
40. [40]
  Leong, W. W. Y.; Chen, X.; Chi, Y. R. Green Chem. 2013, 15, 1505. doi: 10.1039/c3gc40397a
41. [41]
  Raup, D. E.; Cardinal-David, B.; Holte, D.; Scheidt, K. A. Nat. Chem. 2010, 2, 766. doi: 10.1038/nchem.727
42. [42]
  Zhao, X.; DiRocco, D. A.; Rovis, T. J. Am. Chem. Soc. 2011, 133, 12466. doi: 10.1021/ja205714g
43. [43]
  De Vreese, R.; D'Hooghe, M. Beilstein J. Org. Chem. 2012, 8, 398. doi: 10.3762/bjoc.8.43
44. [44]
  Chen, X.; Fang, X.; Chi, Y. R. Chem. Sci. 2013, 4, 2613. doi: 10.1039/c3sc50666e
45. [45]
  Nair, V.; Sinu, C. R.; Babu, B. P.; Varghese, V.; Jose, A.; Suresh, E. Org. Lett. 2009, 11, 5570. doi: 10.1021/ol901918x
46. [46]
  Maji, B.; Ji, L.; Wang, S.; Vedachalam, S.; Ganguly, R.; Liu, X. W. Angew. Chem., Int. Ed. 2012, 51, 8276. doi: 10.1002/anie.v51.33
47. [47]
  White, N. A.; DiRocco, D. A.; Rovis, T. J. Am. Chem. Soc. 2013, 135, 8504. doi: 10.1021/ja403847e
48. [48]
  Cheng, J.; Huang, Z.; Chi, Y. R. Angew. Chem., Int. Ed. 2013, 52, 8592. doi: 10.1002/anie.201303247
49. [49]
  Zhang, Z.; Zeng, X.; Xie, D.; Chen, D.; Ding, L.; Wang, A.; Yang, L.; Zhong, G. Org. Lett. 2015, 17, 5052. doi: 10.1021/acs.orglett.5b02527
50. [50]
  Xia, W.; Yao, H.; Liu, D.; Zhao, L.; Zhou, Y.; Liu, H. Adv. Synth. Catal. 2016, 358, 1864. doi: 10.1002/adsc.201600136
51. [51]
  Lv, H.; Tiwari, B.; Mo, J.; Xing, C.; Chi, Y. R. Org. Lett. 2012, 14, 5412. doi: 10.1021/ol302475g
52. [52]
  Jiang, K.; Tiwari, B.; Chi, Y. R. Org. Lett. 2012, 14, 2382. doi: 10.1021/ol3008028
53. [53]
  Chen, X. Y.; Xia, F.; Cheng, J. T.; Ye, S. Angew. Chem., Int. Ed. 2013, 52, 10644. doi: 10.1002/anie.201305571
54. [54]
  Mo, J.; Shen, L.; Chi, Y. R. Angew. Chem., Int. Ed. 2013, 52, 8588. doi: 10.1002/anie.201302152
55. [55]
  Fu, Z.; Xu, J.; Zhu, T.; Leong, W. W.; Chi, Y. R. Nat. Chem. 2013, 5, 835. doi: 10.1038/nchem.1710
56. [56]
  Xie, Y.; Yu, C.; Li, T.; Tu, S.; Yao, C. Chemistry 2015, 21, 5355. doi: 10.1002/chem.201500345
57. [57]
  Shen, L.-T.; Shao, P.-L.; Ye, S. Adv. Synth. Catal. 2011, 353, 1943. doi: 10.1002/adsc.v353.11/12
58. [58]
  Que, Y.; Li, T.; Yu, C.; Wang, X. S.; Yao, C. J. Org. Chem. 2015, 80, 3289. doi: 10.1021/jo502920w
59. [59]
  Rong, X.; Yao, H.; Xia, W.; Du, Y.; Zhou, Y.; Liu, H. ACS Comb. Sci. 2016, 18, 220. doi: 10.1021/acscombsci.5b00197
60. [60]
  Mo, J.; Chen, X.; Chi, Y. R. J. Am. Chem. Soc. 2012, 134, 8810. doi: 10.1021/ja303618z
61. [61]
  Wang, M.; Huang, Z.; Xu, J.; Chi, Y. R. J. Am. Chem. Soc. 2014, 136, 1214. doi: 10.1021/ja411110f
62. [62]
  Liang, Z.-Q.; Wang, D.-L.; Zhang, H.-M.; Ye, S. Org. Lett. 2015, 17, 5140. doi: 10.1021/acs.orglett.5b02695
63. [63]
  Xu, J.; Yuan, S.; Miao, M. Org. Lett. 2016, 18, 3822. doi: 10.1021/acs.orglett.6b01831
64. [64]
  Xiao, Y.; Wang, J.; Xia, W.; Shu, S.; Jiao, S.; Zhou, Y.; Liu, H. Org. Lett. 2015, 17, 3850. doi: 10.1021/acs.orglett.5b01827
65. [65]
  Chen, X.; Yang, S.; Song, B. A.; Chi, Y. R. Angew. Chem., Int. Ed. 2013, 52, 11134. doi: 10.1002/anie.201305861
66. [66]
  Zhu, T.; Mou, C.; Li, B.; Smetankova, M.; Song, B. A.; Chi, Y. R. J. Am. Chem. Soc. 2015, 137, 5658. doi: 10.1021/jacs.5b02219
67. [67]
  Pellissier, H. Tetrahedron 2008, 64, 1563. doi: 10.1016/j.tet.2007.10.080
68. [68]
  Lu, S.; Poh, S. B.; Siau, W. Y.; Zhao, Y. Angew. Chem., Int. Ed. 2013, 52, 1731. doi: 10.1002/anie.v52.6
69. [69]
  Telfer, S. Coord. Chem. Rev. 2003, 242, 33. doi: 10.1016/S0010-8545(03)00026-2
70. [70]
  Lu, S.; Poh, S. B.; Zhao, Y. Angew. Chem., Int. Ed. 2014, 53, 11041. doi: 10.1002/anie.201406192
71. [71]
  Steinreiber, J.; Faber, K.; Griengl, H. Chemistry 2008, 14, 8060. doi: 10.1002/chem.v14:27
72. [72]
  Cohen, D. T.; Eichman, C. C.; Phillips, E. M.; Zarefsky, E. R.; Scheidt, K. A. Angew. Chem., Int. Ed. 2012, 51, 7309. doi: 10.1002/anie.201203382
73. [73]
  Goodman, C. G.; Johnson, J. S. J. Am. Chem. Soc. 2014, 136, 14698. doi: 10.1021/ja508521a
74. [74]
  Goodman, C. G.; Walker, M. M.; Johnson, J. S. J. Am. Chem. Soc. 2015, 137, 122. doi: 10.1021/ja511701j
75. [75]
  Wu, Z.; Li, F.; Wang, J. Angew. Chem., Int. Ed. 2015, 54, 1629. doi: 10.1002/anie.201410030
76. [76]
  Babu, R. S.; O'Doherty, G. A. J. Am. Chem. Soc. 2003, 125, 12406. doi: 10.1021/ja037097k
77. [77]
  Sugawara, K.; Imanishi, Y.; Hashiyama, T. Tetrahe-dron-Asymmetry 2000, 11, 4529. doi: 10.1016/S0957-4166(00)00424-9
78. [78]
  Chen, X.; Fong, J. Z.; Xu, J.; Mou, C.; Lu, Y.; Yang, S.; Song, B. A.; Chi, Y. R. J. Am. Chem. Soc. 2016, 138, 7212. doi: 10.1021/jacs.6b00406
79. [79]
  White, N. A.; Rovis, T. J. Am. Chem. Soc. 2014, 136, 14674. doi: 10.1021/ja5080739
80. [80]
  Zhang, Y.; Du, Y.; Huang, Z.; Xu, J.; Wu, X.; Wang, Y.; Wang, M.; Yang, S.; Webster, R. D.; Chi, Y. R. J. Am. Chem. Soc. 2015, 137, 2416. doi: 10.1021/ja511371a
81. [81]
  Li, B.-S.; Wang, Y.; Proctor, R. S. J.; Zhang, Y.; Webster, R. D.; Yang, S.; Song, B.; Chi, Y. R. Nat. Commun. 2016, 7.
82. [82]
  Reddi, R. N.; Prasad, P. K.; Sudalai, A. Angew. Chem., Int. Ed. 2015, 54, 14150. doi: 10.1002/anie.201507363
83. [83]
  Nakano, Y.; Lupton, D. W. Angew. Chem., Int. Ed. 2016, 55, 3135. doi: 10.1002/anie.201510106
84. [84]
  Patra, A.; Mukherjee, S.; Das, T. K.; Jain, S.; Gonnade, R. G.; Biju, A. T. Angew. Chem., Int. Ed. 2017, 56, 2730. doi: 10.1002/anie.v56.10
85. [85]
  Ungureanu, A.; Levens, A.; Candish, L.; Lupton, D. W. Angew. Chem., Int. Ed. 2015, 54, 11780. doi: 10.1002/anie.201504633
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]
  Feng Sha , Xinyan Wu , Ping Hu , Wenqing Zhang , Xiaoyang Luan , Yunfei Ma . Design of Course Ideology and Politics for the Comprehensive Organic Synthesis Experiment of Benzocaine. University Chemistry, 2024, 39(2): 110-115. doi: 10.3866/PKU.DXHX202307082
3. [3]
  Ruolin CHENG , Haoran WANG , Jing REN , Yingying MA , Huagen LIANG . Efficient photocatalytic CO₂ cycloaddition over W₁₈O₄₉/NH₂-UiO-66 composite catalyst. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 523-532. doi: 10.11862/CJIC.20230349
4. [4]
  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
5. [5]
  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-. doi: 10.3866/PKU.WHXB202312014
6. [6]
  Yue Wu , Jun Li , Bo Zhang , Yan Yang , Haibo Li , Xian-Xi Zhang . Research on Kinetic and Thermodynamic Transformations of Organic-Inorganic Hybrid Materials for Fluorescent Anti-Counterfeiting Application information: Introducing a Comprehensive Chemistry Experiment. University Chemistry, 2024, 39(6): 390-399. doi: 10.3866/PKU.DXHX202403028
7. [7]
  Jiaqi AN , Yunle LIU , Jianxuan SHANG , Yan GUO , Ce LIU , Fanlong ZENG , Anyang LI , Wenyuan WANG . Reactivity of extremely bulky silylaminogermylene chloride and bonding analysis of a cubic tetragermylene. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1511-1518. doi: 10.11862/CJIC.20240072
8. [8]
  Ke Li , Chuang Liu , Jingping Li , Guohong Wang , Kai Wang . 钛酸铋/氮化碳无机有机复合S型异质结纯水光催化产过氧化氢. Acta Physico-Chimica Sinica, 2024, 40(11): 2403009-. doi: 10.3866/PKU.WHXB202403009
9. [9]
  Wenlong LI , Xinyu JIA , Jie LING , Mengdan MA , Anning ZHOU . Photothermal catalytic CO₂ hydrogenation over a Mg-doped In₂O_3-x catalyst. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 919-929. doi: 10.11862/CJIC.20230421
10. [10]
  Kun WANG , Wenrui LIU , Peng JIANG , Yuhang SONG , Lihua CHEN , Zhao DENG . Hierarchical hollow structured BiOBr-Pt catalysts for photocatalytic CO₂ reduction. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1270-1278. doi: 10.11862/CJIC.20240037
11. [11]
  Guodong Xu , Chengcai Sheng , Xiaomeng Zhao , Tuojiang Zhang , Zongtang Liu , Jun Dong . Reform of Comprehensive Organic Chemistry Experiments in the Context of Emerging Engineering Education: A Case Study on the Improved Preparation of Benzocaine. University Chemistry, 2024, 39(11): 286-295. doi: 10.12461/PKU.DXHX202403094
12. [12]
  Juntao Yan , Liang Wei . 2D S-Scheme Heterojunction Photocatalyst. Acta Physico-Chimica Sinica, 2024, 40(10): 2312024-. doi: 10.3866/PKU.WHXB202312024
13. [13]
  Yuanyin Cui , Jinfeng Zhang , Hailiang Chu , Lixian Sun , Kai Dai . Rational Design of Bismuth Based Photocatalysts for Solar Energy Conversion. Acta Physico-Chimica Sinica, 2024, 40(12): 2405016-. doi: 10.3866/PKU.WHXB202405016
14. [14]
  Dan Li , Hui Xin , Xiaofeng Yi . Comprehensive Experimental Design on Ni-based Catalyst for Biofuel Production. University Chemistry, 2024, 39(8): 204-211. doi: 10.3866/PKU.DXHX202312046
15. [15]
  Aiai WANG , Lu ZHAO , Yunfeng BAI , Feng FENG . Research progress of bimetallic organic framework in tumor diagnosis and treatment. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1825-1839. doi: 10.11862/CJIC.20240225
16. [16]
  Xinyu Zhu , Meili Pang . Application of Functional Group Addition Strategy in Organic Synthesis. University Chemistry, 2024, 39(3): 218-230. doi: 10.3866/PKU.DXHX202308106
17. [17]
  Tianyun Chen , Ruilin Xiao , Xinsheng Gu , Yunyi Shao , Qiujun Lu . Synthesis, Crystal Structure, and Mechanoluminescence Properties of Lanthanide-Based Organometallic Complexes. University Chemistry, 2024, 39(5): 363-370. doi: 10.3866/PKU.DXHX202312017
18. [18]
  Shicheng Yan . Experimental Teaching Design for the Integration of Scientific Research and Teaching: A Case Study on Organic Electrooxidation. University Chemistry, 2024, 39(11): 350-358. doi: 10.12461/PKU.DXHX202408036
19. [19]
  Yong Wang , Yingying Zhao , Boshun Wan . Analysis of Organic Questions in the 37th Chinese Chemistry Olympiad (Preliminary). University Chemistry, 2024, 39(11): 406-416. doi: 10.12461/PKU.DXHX202403009
20. [20]
  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

Get Citation

PDF

XML

Metrics

PDF Downloads(391)
Abstract views(10531)
HTML views(4621)

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