N-杂环卡宾化合物的合成及其在有机合成中的应用

刘波 陈万芝*

引用本文: 刘波, 陈万芝*. 铜N-杂环卡宾化合物的合成及其在有机合成中的应用[J]. 无机化学学报, 2014, 30(1): 20-36. doi: 10.11862/CJIC.2014.068 shu
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

N-杂环卡宾化合物的合成及其在有机合成中的应用

  • 基金项目:

    国家自然科学基金(No.20872129,21072170)资助项目。 

摘要: N-杂环卡宾铜化合物具有简便易得,价廉低毒,性质稳定,结构类型多样并易于修饰等诸多优点,在很多领域具有重要的应用价值,因此铜的N-杂环卡宾化学在过去十几年中得到了快速发展。本文结合我们的工作,总结铜N-杂环卡宾化合物的合成方法、结构特点、转移卡宾配体用于合成其它金属卡宾化合物以及催化应用。

English

  • 
    1. [1] Arduengo A J, Dias H V R, Calabrese J C, et al. Organome-tallics, 1993, 12(9):3405-3409[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[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[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[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[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[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[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[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[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[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[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[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[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[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[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[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[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[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[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[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[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[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[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[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[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[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[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[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[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[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[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[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[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[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[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[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[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[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[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[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[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[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[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[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)[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[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[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[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[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[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[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[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[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[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[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[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[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[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[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[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[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[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[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[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[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[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[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[68] Wang M, Li P, Wang L. Eur. J. Org. Chem., 2008(13):2255-2261

  • 加载中
计量
  • PDF下载量:  706
  • 文章访问数:  1584
  • HTML全文浏览量:  172
文章相关
  • 收稿日期:  2013-09-30
  • 网络出版日期:  2013-11-05
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

  1. 本站搜索
  2. 百度学术搜索
  3. 万方数据库搜索
  4. CNKI搜索

/

返回文章