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