Citation: LIU Bo, CHEN Wan-Zhi*. Synthesis and Applications of Copper N-heterocyclic Carbene Complexes[J]. Chinese Journal of Inorganic Chemistry, ;2014, 30(1): 20-36. doi: 10.11862/CJIC.2014.068 shu

Synthesis and Applications of Copper N-heterocyclic Carbene Complexes

LIU Bo ¹ ,
CHEN Wan-Zhi* ²

1.
1 Shanghai Research Institute of Petrochemical Technology, Sinopec, Shanghai 201208, China;

Received Date: 30 September 2013
Available Online: 5 November 2013
Fund Project:

The N-heterocyclic carbene (NHC) chemistry of copper has been flourishing in the past two decades. Cu-NHC complexes are of low cost and low toxicity which are easily available via various synthetic routes. Their structural diversity and ease of structural modification offer excellent opportunities for their versatile applications in the fields of catalysis, medicine, and materials. This review summarizes the synthetic routes to Cu-NHC complexes, structural features, carbene transfer reactivities and their applications in synthesis of other metal-NHC complexes, as well as their applications in catalysis.
- N-heterocyclic carbenes;copper complexes;synthesis;applications;catalysis,
1. [1]
  [1] Arduengo A J, Dias H V R, Calabrese J C, et al. Organome-tallics, 1993, 12(9):3405-3409
2. [2]
  [2] Jurkauskas V, Sadighi J P, Buchwald S L. Org. Lett., 2003, 5 (14):2417-2420
3. [3]
  [3] Arnold P L, Scarisbrick A C, Blake A J, et al. Chem. Commun., 2001:2340-2341
4. [4]
  [4] Tulloch A A D, Danopoulos A A, Kleinhenz, S, et al. Organ-ometallics, 2001, 20(10):2027-2031
5. [5]
  [5] Citadelle C A, Nouy E L, Bisaro F, et al. Dalton Trans., 2010, 39(19):4489-4491
6. [6]
  [6] Gischig S, Togni A. Organometallics, 2005, 24(2):203-205
7. [7]
  [7] Danopoulos A A, Cole P, Downing S P, et al. J. Organomet. Chem., 2008, 693:3369-3374
8. [8]
  [8] Han X, Koh L L, Liu Z P, et al. Organometallics, 2010, 29(11): 2403-2405
9. [9]
  [9] Zanardi A, Novikov M A, Martin E, et al. J. Am. Chem. Soc., 2011, 133(51):20901-20913
10. [10]
  [10] Grandbois A, Mayer M, Bedard M, et al. Chem. Eur. J., 2009, 15(38):9655-9659
11. [11]
  [11] Pawar G M, Bantu B, Weckesser J, et al. Dalton Trans., 2009 (41):9043-9051
12. [12]
  [12] Gall T L, Baltatu S, Collins S K. Synthesis, 2011(22):3687-3691
13. [13]
  [13] Liu B, Xia Q, Chen W. Angew. Chem., Int. Ed., 2009, 48 (30):5513-5516
14. [14]
  [14] Liu B, Liu B, Zhou Y, et al. Organometallics, 2010, 29(6): 1457-1464
15. [15]
  [15] Liu X, Pan S, Wu J, et al. Organometallics, 2013, 32(1):209-217
16. [16]
  [16] Liu B, Zhang Y, Xu D, et al. Chem. Commun., 2011, 47(10): 2883-2885
17. [17]
  [17] Raubenheimer H G, Cronje S, Rooyen P H, et al. Angew. Chem., Int. Ed., 1994, 33(6):672-673
18. [18]
  [18] Chun J, Jung G, Kim H J, et al. Inorg. Chem., 2009, 48(14): 6353-6355
19. [19]
  [19] Sabiah S, Lee C S, Hwang W S, et al. Organometallics, 2010, 29(2):290-293
20. [20]
  [20] Kolychev E L, Shuntikov V V, Khrustalev V N, et al. Dalton Trans., 2011, 40(12):3074-3076
21. [21]
  [21] Díez-González S, Escudero-Adán E C, Benet-Buchholz J, et al. Dalton Trans., 2010, 39(32):7595-7606
22. [22]
  [22] Díez-González S, Scott N M, Nolan S P. Organometallics, 2006, 25(9):2355-2358
23. [23]
  [23] Venkatachalam G, Heckenroth M, Neels A, et al. Helv. Chim. Acta, 2009, 92(6):1034-1045
24. [24]
  [24] Fortman G C, Slawin A M Z, Nolan S P. Organometallics, 2010, 29(17):3966-3972
25. [25]
  [25] McKie R, Murphy J A, Park S R, et al. Angew. Chem. Int. Ed., 2007, 46(34):6525-6528
26. [26]
  [26] Hu X, Castro-Rodriguez I, Olsen K, et al. Organometallics, 2004, 23(4):755-764
27. [27]
  [27] Biffis A, Tubaro C, Scattolin E, et al. Dalton Trans., 2009 (35):7223-7229
28. [28]
  [28] Chen C, Qiu H, Chen W. J. Organomet. Chem., 2012, 696 (26):4166-4172
29. [29]
  [29] Larsen A O, Leu W, Oberhuber C N, et al. J. Am. Chem. Soc., 2004, 126(36):11130-11131
30. [30]
  [30] Veldhuizen J J V, Campbell J E, Giudici R E, et al. J. Am. Chem. Soc., 2005, 127(18):6877-6882
31. [31]
  [31] Slivarichova M, Ahmad R, Kuo Y Y, et al. Organometallics, 2011, 30(17):4779-4787
32. [32]
  [32] Furst M R L, Cazin C S J. Chem. Commun., 2010, 46(37): 6924-6925
33. [33]
  [33] Gierz V, Maichle-Mossmer C, Kunz D. Organometallics, 2012, 31(2):739-747
34. [34]
  [34] Badaj A C, Lavoie G G. Organometallics, 2012, 31(3):1103-1111
35. [35]
  [35] Liu X, Pattacini R, Deglmann P, et al. Organometallics, 2011, 30(12):3302-3310
36. [36]
  [36] Gomez-Suarez A, Ramon R S, Songis O, et al. Organome-tallics, 2011, 30(20):5463-5470
37. [37]
  [37] Fraser P K, Woodward S. Tetrahedron Lett., 2001, 42(14): 2747-2749
38. [38]
  [38] Díez-González S, Nolan S P. Synlett, 2007(14):2158-2167
39. [39]
  [39] Ohishi T, Nishiura M, Hou Z. Angew. Chem., Int. Ed., 2008, 47(31):5792-5795
40. [40]
  [40] Ohishi T, Zhang L, Nishiura M, et al. Angew. Chem., Int. Ed., 2011, 50(35):8114-8117
41. [41]
  [41] Boogaerts I I F, Fortman G C, Furst M R L, et al. Angew. Chem., Int. Ed., 2010, 49(46): 8674-8677
42. [42]
  [42] Zhang L, Cheng J, Ohishi T, et al. Angew. Chem., Int. Ed., 2010, 49(46):8670-8673
43. [43]
  [43] Yu D, Zhang Y. Proc. Natl. Acad. Sci., 2010, 107(47):20184-20189
44. [44]
  [44] Zhang W Z, Li W J, Zhang X, et al. Org. Lett., 2010, 12(21): 4748-4751
45. [45]
  [45] Fujihara T, Xu T, Semba K, et al. Angew. Chem., Int. Ed., 2011, 50:523-527(2)
46. [46]
  [46] Díez-González S, Nolan S P. Aldrichimica Acta, 2008, 41: 43-51
47. [47]
  [47] Wang W, Wu J, Xia C, et al. Green Chem., 2011, 13(12): 3440-3445
48. [48]
  [48] Nakamura T, Terashima T, Ogata K, et al. Org. Lett., 2011, 13(4):620-623
49. [49]
  [49] Gu S, Xu D, Chen W. Dalton Trans., 2011, 40(7):1576-1583
50. [50]
  [50] Liu B, Chen C, zhang Y, et al. Organometallics, 2013, 32(19): 5451-5460
51. [51]
  [51] Lee K, Hoveyda A H. J. Org. Chem., 2009, 74(12):4455-4462
52. [52]
  [52] Selim K B, Matsumoto Y, Yamada K, et al. Angew. Chem., Int. Ed., 2009, 48(46):8733-8735
53. [53]
  [53] Park J K, Lackey H H, Ondrusek B A, et al. J. Am. Chem. Soc., 2011, 133(8):2410-2413
54. [54]
  [54] Uehling M R, Marionni S T, Lalic G. Org. Lett., 2012, 14(1): 362-365
55. [55]
  [55] Sai M, Yorimitsu H, Oshima K. Angew. Chem., Int. Ed., 2011, 50(14):3294-3298
56. [56]
  [56] Lee Y, Hoveyda A H. J. Am. Chem. Soc., 2009, 131(9):3160-3161
57. [57]
  [57] Park J K, Lackey H H, Rexford M D, et al. Org. Lett., 2010, 12(21):5008-5011
58. [58]
  [58] Jang H, Zhugralin A R, Lee Y, et al. J. Am. Chem. Soc., 2011, 133(20):7859-7871
59. [59]
  [59] Lee Y, Jang H, Hoveyda A H. J. Am. Chem. Soc., 2009, 131 (51):18234-18235
60. [60]
  [60] Tubaro C, Bifs A, Scattolin E, et al. Tetrahedron, 2008, 64 (19):4187-4195
61. [61]
  [61] Ellul C E, Reed G, Mahon M F, et al. Organometallics, 2010, 29(18):4097-4104
62. [62]
  [62] Delp S A, Goj L A, Pouy M J, et al. Organometallics, 2011, 30(1):55-57
63. [63]
  [63] Chen C, Liu B, Chen W. Synthesis, 2013, 45:3387-3391
64. [64]
  [64] Liu X, Xia Q, Zhang Y, et al. J. Org. Chem., 2013, 78(17): 8531-8536
65. [65]
  [65] Fructos M R, Belderrain T R, Nicasio M C, et al. J. Am. Chem. Soc., 2004, 126(35):10846-10847
66. [66]
  [66] Lebel H, Davi M, Díez-González S, et al. J. Org. Chem., 2007, 72(1):144-149
67. [67]
  [67] Bantu B, Wang D, Wurst K, et al. Tetrahedron, 2005, 61(51): 12145-12152
68. [68]
  [68] Wang M, Li P, Wang L. Eur. J. Org. Chem., 2008(13):2255-2261
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