注册 English

过渡金属配合物催化乙腈碳碳单键断裂的研究进展

陈慧晴 ,  张坤 ,  徐枫 ,  黄伟

downloadPDF
引用本文: 陈慧晴, 张坤, 徐枫, 黄伟. 过渡金属配合物催化乙腈碳碳单键断裂的研究进展[J]. 无机化学学报, 2013, 29(11): 2265-2275. doi: 10.3969/j.issn.1001-4861.2013.00.352 shu
Citation:  CHEN Hui-Qing, ZHANG Kun, XU Feng, HUANG Wei. Progress of the C-C Bond Cleavage in Acetonitrile Catalyzed by Transition-Metal Complexes[J]. Chinese Journal of Inorganic Chemistry, 2013, 29(11): 2265-2275. doi: 10.3969/j.issn.1001-4861.2013.00.352 shu

过渡金属配合物催化乙腈碳碳单键断裂的研究进展

  • 基金项目:

    国家自然科学基金(No.21171088) (No.21171088)

    青蓝工程资助项目。 

摘要: 有机化合物中的碳碳单键断裂反应是一类非常重要而且具有挑战性的反应,过去的几十年中,关于有机腈类化合物中碳碳单键的催化断裂反应研究受到了很多的关注。而乙腈作为常用的有机溶剂之一,其分子是有机腈类中的最小分子。本文结合最近几年国内外及本课题组关于乙腈分子的碳碳单键活化断裂的研究,综述了各类过渡金属配合物催化乙腈分子碳碳单键断裂的研究进展,分析了当前存在的问题,提出了对今后研究的展望。

English

  • 

    1. [1] Yu D H, Shen Q L, Lu L. J. Org. Chem., 2012,77:1798-804[1] Yu D H, Shen Q L, Lu L. J. Org. Chem., 2012,77:1798-804

    2. [2] Murahashi S I, Nakae T, Terai H, et al. J. Am. Chem. Soc., 2008,130:11005-11012[2] Murahashi S I, Nakae T, Terai H, et al. J. Am. Chem. Soc., 2008,130:11005-11012

    3. [3] Gunay A, Jones W D. J. Am. Chem. Soc., 2007,129:8729-8735[3] Gunay A, Jones W D. J. Am. Chem. Soc., 2007,129:8729-8735

    4. [4] Hughes R P, Laritchev R B, Zakharov L N, et al. J. Am. Chem. Soc., 2005,127:6325-6334[4] Hughes R P, Laritchev R B, Zakharov L N, et al. J. Am. Chem. Soc., 2005,127:6325-6334

    5. [5] Jun C H. Chem. Soc. Rev., 2004,33:610-618[5] Jun C H. Chem. Soc. Rev., 2004,33:610-618

    6. [6] Hughes R P, Zhang D H, Zakharov L N, et al. Organometallics, 2002,1:4902-4904[6] Hughes R P, Zhang D H, Zakharov L N, et al. Organometallics, 2002,1:4902-4904

    7. [7] Mueller C, Lachicotte R J, Jones W D. Organometallics, 2002, 21:1975-1981[7] Mueller C, Lachicotte R J, Jones W D. Organometallics, 2002, 21:1975-1981

    8. [8] Ananikov V P, Musaev D G, Morokuma K. J. Am. Chem. Soc., 2002,124:2839-2852[8] Ananikov V P, Musaev D G, Morokuma K. J. Am. Chem. Soc., 2002,124:2839-2852

    9. [9] Jun C H, Lee D Y, Kim Y H, et al. Organometallics, 2001, 20:2928-2931[9] Jun C H, Lee D Y, Kim Y H, et al. Organometallics, 2001, 20:2928-2931

    10. [10]Cohen R, Van der Boom M E, Shimon L J W, et al. J. Am. Chem. Soc., 2000,122:7723-7734[10]Cohen R, Van der Boom M E, Shimon L J W, et al. J. Am. Chem. Soc., 2000,122:7723-7734

    11. [11]Meredith J M, Robinson R, Goldberg K I, et al. Organome-tallics, 2012,31:1879-1887[11]Meredith J M, Robinson R, Goldberg K I, et al. Organome-tallics, 2012,31:1879-1887

    12. [12]Han Y F, Lin Y J, Hor T S A, et al. Organometallics, 2012, 31:995-1000[12]Han Y F, Lin Y J, Hor T S A, et al. Organometallics, 2012, 31:995-1000

    13. [13]Baillie R A, Tran T, Lalonde K M, et al. Organometallics, 2012,31:1055-1067[13]Baillie R A, Tran T, Lalonde K M, et al. Organometallics, 2012,31:1055-1067

    14. [14]Balcells D, Clot E, Eisenstein O. Chem. Rev., 2010,110: 749-823[14]Balcells D, Clot E, Eisenstein O. Chem. Rev., 2010,110: 749-823

    15. [15]Michel C, Belanzoni P, Gamez P, et al. Inorg. Chem., 2009, 48:11909-11920[15]Michel C, Belanzoni P, Gamez P, et al. Inorg. Chem., 2009, 48:11909-11920

    16. [16]Zakzeski J, Behn A, Head-Gordon M, et al. J. Am. Chem. Soc., 2009,131:11098-11105[16]Zakzeski J, Behn A, Head-Gordon M, et al. J. Am. Chem. Soc., 2009,131:11098-11105

    17. [17]Fout A R, Scott J, Miller D L, et al. Organometallics, 2009, 28:331-347[17]Fout A R, Scott J, Miller D L, et al. Organometallics, 2009, 28:331-347

    18. [18]Ohki Y, Hatanaka T, Tatsumi K. J. Am. Chem. Soc., 2008, 130:17174-17186[18]Ohki Y, Hatanaka T, Tatsumi K. J. Am. Chem. Soc., 2008, 130:17174-17186

    19. [19]Nakao Y, Kashihara N, Kanyiva K S, et al. J. Am. Chem. Soc., 2008,130:16170-16171[19]Nakao Y, Kashihara N, Kanyiva K S, et al. J. Am. Chem. Soc., 2008,130:16170-16171

    20. [20]Whited M T, Grubbs R H. Organometallics, 2008,27:5737-6042[20]Whited M T, Grubbs R H. Organometallics, 2008,27:5737-6042

    21. [21]Kavara A, Cousineau K D, Rohr A D, et al. Organometallics, 2008,27:1041-1043[21]Kavara A, Cousineau K D, Rohr A D, et al. Organometallics, 2008,27:1041-1043

    22. [22]Zimmermann M, Estler F, Herdtweck E, et al. Organometallics, 2007,26:6029-6041[22]Zimmermann M, Estler F, Herdtweck E, et al. Organometallics, 2007,26:6029-6041

    23. [23]Liang L C, Chien P S, Huang Y L. J. Am. Chem. Soc., 2006,128:15562-15563[23]Liang L C, Chien P S, Huang Y L. J. Am. Chem. Soc., 2006,128:15562-15563

    24. [24]Liang L C, Lin J M, Lee W Y. Chem. Commun., 2005:2462-2464[24]Liang L C, Lin J M, Lee W Y. Chem. Commun., 2005:2462-2464

    25. [25]Kumar R K, Ali M A, Punniyamurthy T. Org. Lett., 2011, 13:2102-2105[25]Kumar R K, Ali M A, Punniyamurthy T. Org. Lett., 2011, 13:2102-2105

    26. [26]Novarino E, Guerrero Rios I, S van der Veer, et al. Organo-metallics, 2011,30:92-99[26]Novarino E, Guerrero Rios I, S van der Veer, et al. Organo-metallics, 2011,30:92-99

    27. [27]Ke Z F, Cundari T R. Organometallics, 2010,29:821-834[27]Ke Z F, Cundari T R. Organometallics, 2010,29:821-834

    28. [28]Hu Y C, Tsai C C, Shih W C, et al. Organometallics, 2010, 29:516-518[28]Hu Y C, Tsai C C, Shih W C, et al. Organometallics, 2010, 29:516-518

    29. [29]Sabiah S, Lee C S, Hwang W S, et al. Organometallics, 2010,29:290-293[29]Sabiah S, Lee C S, Hwang W S, et al. Organometallics, 2010,29:290-293

    30. [30]Zhu B, Wang G W. Org. Lett., 2009,11:4334-4337[30]Zhu B, Wang G W. Org. Lett., 2009,11:4334-4337

    31. [31]Erhardt S, Grushin V V, Kilpatrick A H, et al. J. Am. Chem. Soc., 2008,130:4828-4845[31]Erhardt S, Grushin V V, Kilpatrick A H, et al. J. Am. Chem. Soc., 2008,130:4828-4845

    32. [32]Cameron T M, Abboud K A, Boncella J M. Chem. Commun., 2001,13:1224-1225[32]Cameron T M, Abboud K A, Boncella J M. Chem. Commun., 2001,13:1224-1225

    33. [33]Kumar R K, Ali M A, Punniyamurthy T. Org. Lett., 2011, 13:2102-2105[33]Kumar R K, Ali M A, Punniyamurthy T. Org. Lett., 2011, 13:2102-2105

    34. [34]Burmeister J L, Edwards L M. J. Chem. Soc. A, 1971:1663-1666[34]Burmeister J L, Edwards L M. J. Chem. Soc. A, 1971:1663-1666

    35. [35]Gerlach D H, Kane A R, Parshall G W, et al. J. Am. Chem. Soc., 1971,93:3543-3544[35]Gerlach D H, Kane A R, Parshall G W, et al. J. Am. Chem. Soc., 1971,93:3543-3544

    36. [36]Cassar L. J. Organomet. Chem., 1973,54:C57-C58[36]Cassar L. J. Organomet. Chem., 1973,54:C57-C58

    37. [37]Parshall G W. J. Am. Chem. Soc., 1974,96:2360-2366[37]Parshall G W. J. Am. Chem. Soc., 1974,96:2360-2366

    38. [38]Favero G, Morvillo A, Turco A. J. Organomet. Chem., 1983, 241:251-257[38]Favero G, Morvillo A, Turco A. J. Organomet. Chem., 1983, 241:251-257

    39. [39]Miller J A. Tetrahedron Lett., 2001,42:6991-6993[39]Miller J A. Tetrahedron Lett., 2001,42:6991-6993

    40. [40]Bianchini C, Masi D, Meli A, et al. Organometallics, 1986, 5:1670-1675[40]Bianchini C, Masi D, Meli A, et al. Organometallics, 1986, 5:1670-1675

    41. [41]Abla M, Yamamoto T. J. Organomet. Chem., 1997,532:267-270[41]Abla M, Yamamoto T. J. Organomet. Chem., 1997,532:267-270

    42. [42]Brunkan N M, Brestensky D M, Jones W D. J. Am. Chem. Soc., 2004,126:3627-3641[42]Brunkan N M, Brestensky D M, Jones W D. J. Am. Chem. Soc., 2004,126:3627-3641

    43. [43]Liu Q X, Xu F B, Li Q S, et al. Organometallics, 2004,23: 610-614[43]Liu Q X, Xu F B, Li Q S, et al. Organometallics, 2004,23: 610-614

    44. [44]Nishihara Y, Inoue Y, Itazaki M, et al. Org. Lett., 2005,7: 2639-2641[44]Nishihara Y, Inoue Y, Itazaki M, et al. Org. Lett., 2005,7: 2639-2641

    45. [45]Garcia J J, Brunkan N M, Jones W D. J. Am. Chem. Soc., 2002,124:9547-9555[45]Garcia J J, Brunkan N M, Jones W D. J. Am. Chem. Soc., 2002,124:9547-9555

    46. [46]Garcia J J, Arevalo A, Brunkan N M, et al. Organometallics, 2004,23:3997-4002[46]Garcia J J, Arevalo A, Brunkan N M, et al. Organometallics, 2004,23:3997-4002

    47. [47]Brunkan N M, Brestensky D M, Jones W D. J. Am. Chem. Soc., 2004,126:3627-3641[47]Brunkan N M, Brestensky D M, Jones W D. J. Am. Chem. Soc., 2004,126:3627-3641

    48. [48]Atesin T A, Li T, Lachaize S, et al. J. Am. Chem. Soc., 2007,129:7562-7562[48]Atesin T A, Li T, Lachaize S, et al. J. Am. Chem. Soc., 2007,129:7562-7562

    49. [49]Swartz B D, Reinartz N M, Brennessel W W, et al. J. Am. Chem. Soc., 2008,130:8548-8554[49]Swartz B D, Reinartz N M, Brennessel W W, et al. J. Am. Chem. Soc., 2008,130:8548-8554

    50. [50]Evans M E, Li T, Jones W D. J. Am. Chem. Soc., 2010, 132:16278-16284[50]Evans M E, Li T, Jones W D. J. Am. Chem. Soc., 2010, 132:16278-16284

    51. [51]Tanabe T, Evans M E, Brennessel W W, et al. Organomet-allics, 2011,30:834-843[51]Tanabe T, Evans M E, Brennessel W W, et al. Organomet-allics, 2011,30:834-843

    52. [52]Evans M E, Jones W D. Organometallics, 2011,30:3371-3377[52]Evans M E, Jones W D. Organometallics, 2011,30:3371-3377

    53. [53]Taw F L, White P S, Bergman R G, et al. J. Am. Chem. Soc., 2002,124:4192-4193[53]Taw F L, White P S, Bergman R G, et al. J. Am. Chem. Soc., 2002,124:4192-4193

    54. [54]Taw F L, Mueller A H, Bergman R G, et al. J. Am. Chem. Soc., 2003,125:9808-9813[54]Taw F L, Mueller A H, Bergman R G, et al. J. Am. Chem. Soc., 2003,125:9808-9813

    55. [55]Klei S R, Tilley T D, Bergman R G. Organometallics, 2002, 21:4648-4661[55]Klei S R, Tilley T D, Bergman R G. Organometallics, 2002, 21:4648-4661

    56. [56]Evans M E, Li Ting, Jones W D. J. Am. Chem. Soc., 2010, 132:16278-16284[56]Evans M E, Li Ting, Jones W D. J. Am. Chem. Soc., 2010, 132:16278-16284

    57. [57]Nakazawa H, Kawasaki T, Miyoshi K, et al. Organometallics, 2004,23:117-126[57]Nakazawa H, Kawasaki T, Miyoshi K, et al. Organometallics, 2004,23:117-126

    58. [58]Nakazawa H, Kamata K, Itazaki M. Chem. Commun., 2005: 4004-4006[58]Nakazawa H, Kamata K, Itazaki M. Chem. Commun., 2005: 4004-4006

    59. [59]Nakazawa H, Itazaki M, Kamata K, et al. Chem. Asian J., 2007,2:882-888[59]Nakazawa H, Itazaki M, Kamata K, et al. Chem. Asian J., 2007,2:882-888

    60. [60]Churchill D, Shin J H, Hascall T, et al. Organometallics, 1999,18:2403-2406[60]Churchill D, Shin J H, Hascall T, et al. Organometallics, 1999,18:2403-2406

    61. [61]Liu Q X, Xu F B, Li Q S, et al. Organometallics, 2004,23: 610-614[61]Liu Q X, Xu F B, Li Q S, et al. Organometallics, 2004,23: 610-614

    62. [62]Zhang X M, Fang R Q. Inorg. Chem., 2005,44:3955-3959[62]Zhang X M, Fang R Q. Inorg. Chem., 2005,44:3955-3959

    63. [63]Guo L R, Bao S S, Li Y Z, et al. Chem. Commun., 2009: 2893-2895[63]Guo L R, Bao S S, Li Y Z, et al. Chem. Commun., 2009: 2893-2895

    64. [64]Marlin D S, Olmstead M M, Mascharak P K. Angew. Chem. Int. Ed., 2001,40:4752-4754[64]Marlin D S, Olmstead M M, Mascharak P K. Angew. Chem. Int. Ed., 2001,40:4752-4754

    65. [65]Li L L, Liu L L, Ren Z G, et al. Cryst. Eng. Comm., 2009, 11:2751-2756[65]Li L L, Liu L L, Ren Z G, et al. Cryst. Eng. Comm., 2009, 11:2751-2756

    66. [66]Zhu Y L, Qu L L, Zhang J, et al. Inorg. Chem. Commun., 2011,14:1644-1647[66]Zhu Y L, Qu L L, Zhang J, et al. Inorg. Chem. Commun., 2011,14:1644-1647

    67. [67]Cui J H, Huang L F, Lu Z Z, et al. Cryst. Eng. Comm., 2012,14:2258-2267[67]Cui J H, Huang L F, Lu Z Z, et al. Cryst. Eng. Comm., 2012,14:2258-2267

    68. [68]Lu T B, Zhuang X M, Li Y W, et al. J. Am. Chem. Soc., 2004,126:4760-4761[68]Lu T B, Zhuang X M, Li Y W, et al. J. Am. Chem. Soc., 2004,126:4760-4761

    69. [69]Bond A D, Derossi S, Jensen F, et al. Inorg. Chem., 2005, 44:5987-5989[69]Bond A D, Derossi S, Jensen F, et al. Inorg. Chem., 2005, 44:5987-5989

    70. [70]Yang L Z, Li Y, Zhuang X M, et al. Chem. Eur. J., 2009,15: 12399-12407[70]Yang L Z, Li Y, Zhuang X M, et al. Chem. Eur. J., 2009,15: 12399-12407

    71. [71]Xu F, Huang W, You X Z. Dalton Trans., 2010,39:10652-10658[71]Xu F, Huang W, You X Z. Dalton Trans., 2010,39:10652-10658

    72. [72]Xu F, Tao T, Zhang K, et al. Dalton Trans., 2013,42:3631-3645[72]Xu F, Tao T, Zhang K, et al. Dalton Trans., 2013,42:3631-3645

    73. [73]Huang W, Xu F, You X Z. Chinese Patent, 201010123274.1. 2012-05-23.[73]Huang W, Xu F, You X Z. Chinese Patent, 201010123274.1. 2012-05-23.

    74. [74]Xu F, Tao T, Liu Q Q, et al. Inorg. Chim. Acta, 2012,392: 465-468[74]Xu F, Tao T, Liu Q Q, et al. Inorg. Chim. Acta, 2012,392: 465-468

    75. [75]Hu B, Fu S J, Xu F, et al. J. Org. Chem., 2011,76:4444-4456[75]Hu B, Fu S J, Xu F, et al. J. Org. Chem., 2011,76:4444-4456

    76. [76]Xu F, Peng Y X, Hu B, et al. CrystEngComm, 2012,14: 8023-8032[76]Xu F, Peng Y X, Hu B, et al. CrystEngComm, 2012,14: 8023-8032

    77. [77]Huang W, Tanaka H, Ogawa T. J. Phys. Chem. C, 2008, 112:11513-11526[77]Huang W, Tanaka H, Ogawa T. J. Phys. Chem. C, 2008, 112:11513-11526

    78. [78]Huang W, Masuda G, Maeda S, et al. Inorg. Chem., 2008, 47:468-480[78]Huang W, Masuda G, Maeda S, et al. Inorg. Chem., 2008, 47:468-480

    79. [79]Wang L, You W, Huang W, et al. Inorg. Chem., 2009,48: 4295-4305[79]Wang L, You W, Huang W, et al. Inorg. Chem., 2009,48: 4295-4305

    80. [80]Huang W, Wang L, Tanaka H, et al. Eur. J. Inorg. Chem., 2009:1321-1331[80]Huang W, Wang L, Tanaka H, et al. Eur. J. Inorg. Chem., 2009:1321-1331

    81. [81]Zhang B, Cao K S, Xu Z A, et al. Eur. J. Inorg. Chem., 2012,24:3844-3851[81]Zhang B, Cao K S, Xu Z A, et al. Eur. J. Inorg. Chem., 2012,24:3844-3851

    82. [82]Huang W, Tanaka H, Ogawa T, et al. Adv. Mater., 2010, 22:2753-2758[82]Huang W, Tanaka H, Ogawa T, et al. Adv. Mater., 2010, 22:2753-2758

    83. [83]Hu B, Xu F, Fu S J, et al. Inorg. Chim. Acta, 2010,363: 1348-1354[83]Hu B, Xu F, Fu S J, et al. Inorg. Chim. Acta, 2010,363: 1348-1354

    84. [84]Wang L, Tao T, Fu S J, et al. CrystEngComm, 2011,13:747-749[84]Wang L, Tao T, Fu S J, et al. CrystEngComm, 2011,13:747-749

    85. [85]Fu S J, Wang L, Tao T, et al. CrystEngComm, 2011,13: 6192-6199[85]Fu S J, Wang L, Tao T, et al. CrystEngComm, 2011,13: 6192-6199

    86. [86]Hu B, Liu Q Q, Tao T, et al. Inorg. Chim. Acta, 2013,394: 576-582[86]Hu B, Liu Q Q, Tao T, et al. Inorg. Chim. Acta, 2013,394: 576-582

    87. [87]Tao T, Peng Y X, Huang W, et al. J. Org. Chem., 2013,78: 2472-2481[87]Tao T, Peng Y X, Huang W, et al. J. Org. Chem., 2013,78: 2472-2481

    88. [88]Hu B, Chen X X, Huang W, et al. Dalton Trans., 2012,41: 14309-14315[88]Hu B, Chen X X, Huang W, et al. Dalton Trans., 2012,41: 14309-14315

    89. [89]Tao T, Wang X X, Wang Y N, et al. Inorg. Chem. Commun., 2013,31:62-65[89]Tao T, Wang X X, Wang Y N, et al. Inorg. Chem. Commun., 2013,31:62-65

    90. [90]XU Feng(徐枫). Thesis for the Doctorate of Nanjing University(南京大学博士论文). 2012.[90]XU Feng(徐枫). Thesis for the Doctorate of Nanjing University(南京大学博士论文). 2012.

  • 加载中
WeChat 扫一扫看文章
计量
  • PDF下载量:  0
  • 文章访问数:  365
  • HTML全文浏览量:  32
文章相关
  • 收稿日期:  2013-01-23
  • 网络出版日期:  2013-05-22
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

All Rights Reserved by the Chinese Chemical Society   中国化学会 版权所有 京ICP备05002797号

本系统由北京仁和汇智信息技术有限公司开发    技术支持: info@rhhz.net