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

Progress of the C-C Bond Cleavage in Acetonitrile Catalyzed by Transition-Metal Complexes

1.
State Key Laboratory of Coordination Chemistry, Nanjing National Laboratory of Microstructures, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210093, China

Received Date: 23 January 2013
Available Online: 22 May 2013
Fund Project: 国家自然科学基金(No.21171088) (No.21171088)

The cleavage of C-C bond is one sort of important and challenging reactions, and much attention has been focused upon the catalytic reactions of the C-C bond cleavage of nitriles during the last few decades. As a commonly used organic solvent, acetonitrile is the smallest one among nitriles. Based on the recent investigations, this paper summarizes the related research advancements of the cleavage of C-C bond in acetonitrile catalyzed by transition-metal complexes, analyses the present problems and gives the researching prospects of this type of reactions.
- cleavage of carbon-carbon bond;acetonitrile;transition-metal complexes;catalytic reaction
1. [1]
  [1] Yu D H, Shen Q L, Lu L. J. Org. Chem., 2012,77:1798-804
2. [2]
  [2] Murahashi S I, Nakae T, Terai H, et al. J. Am. Chem. Soc., 2008,130:11005-11012
3. [3]
  [3] Gunay A, Jones W D. J. Am. Chem. Soc., 2007,129:8729-8735
4. [4]
  [4] Hughes R P, Laritchev R B, Zakharov L N, et al. J. Am. Chem. Soc., 2005,127:6325-6334
5. [5]
  [5] Jun C H. Chem. Soc. Rev., 2004,33:610-618
6. [6]
  [6] Hughes R P, Zhang D H, Zakharov L N, et al. Organometallics, 2002,1:4902-4904
7. [7]
  [7] Mueller C, Lachicotte R J, Jones W D. Organometallics, 2002, 21:1975-1981
8. [8]
  [8] Ananikov V P, Musaev D G, Morokuma K. J. Am. Chem. Soc., 2002,124:2839-2852
9. [9]
  [9] Jun C H, Lee D Y, Kim Y H, et al. Organometallics, 2001, 20:2928-2931
10. [10]
  [10]Cohen R, Van der Boom M E, Shimon L J W, et al. J. Am. Chem. Soc., 2000,122:7723-7734
11. [11]
  [11]Meredith J M, Robinson R, Goldberg K I, et al. Organome-tallics, 2012,31:1879-1887
12. [12]
  [12]Han Y F, Lin Y J, Hor T S A, et al. Organometallics, 2012, 31:995-1000
13. [13]
  [13]Baillie R A, Tran T, Lalonde K M, et al. Organometallics, 2012,31:1055-1067
14. [14]
  [14]Balcells D, Clot E, Eisenstein O. Chem. Rev., 2010,110: 749-823
15. [15]
  [15]Michel C, Belanzoni P, Gamez P, et al. Inorg. Chem., 2009, 48:11909-11920
16. [16]
  [16]Zakzeski J, Behn A, Head-Gordon M, et al. J. Am. Chem. Soc., 2009,131:11098-11105
17. [17]
  [17]Fout A R, Scott J, Miller D L, et al. Organometallics, 2009, 28:331-347
18. [18]
  [18]Ohki Y, Hatanaka T, Tatsumi K. J. Am. Chem. Soc., 2008, 130:17174-17186
19. [19]
  [19]Nakao Y, Kashihara N, Kanyiva K S, et al. J. Am. Chem. Soc., 2008,130:16170-16171
20. [20]
  [20]Whited M T, Grubbs R H. Organometallics, 2008,27:5737-6042
21. [21]
  [21]Kavara A, Cousineau K D, Rohr A D, et al. Organometallics, 2008,27:1041-1043
22. [22]
  [22]Zimmermann M, Estler F, Herdtweck E, et al. Organometallics, 2007,26:6029-6041
23. [23]
  [23]Liang L C, Chien P S, Huang Y L. J. Am. Chem. Soc., 2006,128:15562-15563
24. [24]
  [24]Liang L C, Lin J M, Lee W Y. Chem. Commun., 2005:2462-2464
25. [25]
  [25]Kumar R K, Ali M A, Punniyamurthy T. Org. Lett., 2011, 13:2102-2105
26. [26]
  [26]Novarino E, Guerrero Rios I, S van der Veer, et al. Organo-metallics, 2011,30:92-99
27. [27]
  [27]Ke Z F, Cundari T R. Organometallics, 2010,29:821-834
28. [28]
  [28]Hu Y C, Tsai C C, Shih W C, et al. Organometallics, 2010, 29:516-518
29. [29]
  [29]Sabiah S, Lee C S, Hwang W S, et al. Organometallics, 2010,29:290-293
30. [30]
  [30]Zhu B, Wang G W. Org. Lett., 2009,11:4334-4337
31. [31]
  [31]Erhardt S, Grushin V V, Kilpatrick A H, et al. J. Am. Chem. Soc., 2008,130:4828-4845
32. [32]
  [32]Cameron T M, Abboud K A, Boncella J M. Chem. Commun., 2001,13:1224-1225
33. [33]
  [33]Kumar R K, Ali M A, Punniyamurthy T. Org. Lett., 2011, 13:2102-2105
34. [34]
  [34]Burmeister J L, Edwards L M. J. Chem. Soc. A, 1971:1663-1666
35. [35]
  [35]Gerlach D H, Kane A R, Parshall G W, et al. J. Am. Chem. Soc., 1971,93:3543-3544
36. [36]
  [36]Cassar L. J. Organomet. Chem., 1973,54:C57-C58
37. [37]
  [37]Parshall G W. J. Am. Chem. Soc., 1974,96:2360-2366
38. [38]
  [38]Favero G, Morvillo A, Turco A. J. Organomet. Chem., 1983, 241:251-257
39. [39]
  [39]Miller J A. Tetrahedron Lett., 2001,42:6991-6993
40. [40]
  [40]Bianchini C, Masi D, Meli A, et al. Organometallics, 1986, 5:1670-1675
41. [41]
  [41]Abla M, Yamamoto T. J. Organomet. Chem., 1997,532:267-270
42. [42]
  [42]Brunkan N M, Brestensky D M, Jones W D. J. Am. Chem. Soc., 2004,126:3627-3641
43. [43]
  [43]Liu Q X, Xu F B, Li Q S, et al. Organometallics, 2004,23: 610-614
44. [44]
  [44]Nishihara Y, Inoue Y, Itazaki M, et al. Org. Lett., 2005,7: 2639-2641
45. [45]
  [45]Garcia J J, Brunkan N M, Jones W D. J. Am. Chem. Soc., 2002,124:9547-9555
46. [46]
  [46]Garcia J J, Arevalo A, Brunkan N M, et al. Organometallics, 2004,23:3997-4002
47. [47]
  [47]Brunkan N M, Brestensky D M, Jones W D. J. Am. Chem. Soc., 2004,126:3627-3641
48. [48]
  [48]Atesin T A, Li T, Lachaize S, et al. J. Am. Chem. Soc., 2007,129:7562-7562
49. [49]
  [49]Swartz B D, Reinartz N M, Brennessel W W, et al. J. Am. Chem. Soc., 2008,130:8548-8554
50. [50]
  [50]Evans M E, Li T, Jones W D. J. Am. Chem. Soc., 2010, 132:16278-16284
51. [51]
  [51]Tanabe T, Evans M E, Brennessel W W, et al. Organomet-allics, 2011,30:834-843
52. [52]
  [52]Evans M E, Jones W D. Organometallics, 2011,30:3371-3377
53. [53]
  [53]Taw F L, White P S, Bergman R G, et al. J. Am. Chem. Soc., 2002,124:4192-4193
54. [54]
  [54]Taw F L, Mueller A H, Bergman R G, et al. J. Am. Chem. Soc., 2003,125:9808-9813
55. [55]
  [55]Klei S R, Tilley T D, Bergman R G. Organometallics, 2002, 21:4648-4661
56. [56]
  [56]Evans M E, Li Ting, Jones W D. J. Am. Chem. Soc., 2010, 132:16278-16284
57. [57]
  [57]Nakazawa H, Kawasaki T, Miyoshi K, et al. Organometallics, 2004,23:117-126
58. [58]
  [58]Nakazawa H, Kamata K, Itazaki M. Chem. Commun., 2005: 4004-4006
59. [59]
  [59]Nakazawa H, Itazaki M, Kamata K, et al. Chem. Asian J., 2007,2:882-888
60. [60]
  [60]Churchill D, Shin J H, Hascall T, et al. Organometallics, 1999,18:2403-2406
61. [61]
  [61]Liu Q X, Xu F B, Li Q S, et al. Organometallics, 2004,23: 610-614
62. [62]
  [62]Zhang X M, Fang R Q. Inorg. Chem., 2005,44:3955-3959
63. [63]
  [63]Guo L R, Bao S S, Li Y Z, et al. Chem. Commun., 2009: 2893-2895
64. [64]
  [64]Marlin D S, Olmstead M M, Mascharak P K. Angew. Chem. Int. Ed., 2001,40:4752-4754
65. [65]
  [65]Li L L, Liu L L, Ren Z G, et al. Cryst. Eng. Comm., 2009, 11:2751-2756
66. [66]
  [66]Zhu Y L, Qu L L, Zhang J, et al. Inorg. Chem. Commun., 2011,14:1644-1647
67. [67]
  [67]Cui J H, Huang L F, Lu Z Z, et al. Cryst. Eng. Comm., 2012,14:2258-2267
68. [68]
  [68]Lu T B, Zhuang X M, Li Y W, et al. J. Am. Chem. Soc., 2004,126:4760-4761
69. [69]
  [69]Bond A D, Derossi S, Jensen F, et al. Inorg. Chem., 2005, 44:5987-5989
70. [70]
  [70]Yang L Z, Li Y, Zhuang X M, et al. Chem. Eur. J., 2009,15: 12399-12407
71. [71]
  [71]Xu F, Huang W, You X Z. Dalton Trans., 2010,39:10652-10658
72. [72]
  [72]Xu F, Tao T, Zhang K, et al. Dalton Trans., 2013,42:3631-3645
73. [73]
  [73]Huang W, Xu F, You X Z. Chinese Patent, 201010123274.1. 2012-05-23.
74. [74]
  [74]Xu F, Tao T, Liu Q Q, et al. Inorg. Chim. Acta, 2012,392: 465-468
75. [75]
  [75]Hu B, Fu S J, Xu F, et al. J. Org. Chem., 2011,76:4444-4456
76. [76]
  [76]Xu F, Peng Y X, Hu B, et al. CrystEngComm, 2012,14: 8023-8032
77. [77]
  [77]Huang W, Tanaka H, Ogawa T. J. Phys. Chem. C, 2008, 112:11513-11526
78. [78]
  [78]Huang W, Masuda G, Maeda S, et al. Inorg. Chem., 2008, 47:468-480
79. [79]
  [79]Wang L, You W, Huang W, et al. Inorg. Chem., 2009,48: 4295-4305
80. [80]
  [80]Huang W, Wang L, Tanaka H, et al. Eur. J. Inorg. Chem., 2009:1321-1331
81. [81]
  [81]Zhang B, Cao K S, Xu Z A, et al. Eur. J. Inorg. Chem., 2012,24:3844-3851
82. [82]
  [82]Huang W, Tanaka H, Ogawa T, et al. Adv. Mater., 2010, 22:2753-2758
83. [83]
  [83]Hu B, Xu F, Fu S J, et al. Inorg. Chim. Acta, 2010,363: 1348-1354
84. [84]
  [84]Wang L, Tao T, Fu S J, et al. CrystEngComm, 2011,13:747-749
85. [85]
  [85]Fu S J, Wang L, Tao T, et al. CrystEngComm, 2011,13: 6192-6199
86. [86]
  [86]Hu B, Liu Q Q, Tao T, et al. Inorg. Chim. Acta, 2013,394: 576-582
87. [87]
  [87]Tao T, Peng Y X, Huang W, et al. J. Org. Chem., 2013,78: 2472-2481
88. [88]
  [88]Hu B, Chen X X, Huang W, et al. Dalton Trans., 2012,41: 14309-14315
89. [89]
  [89]Tao T, Wang X X, Wang Y N, et al. Inorg. Chem. Commun., 2013,31:62-65
90. [90]
  [90]XU Feng(徐枫). Thesis for the Doctorate of Nanjing University(南京大学博士论文). 2012.
1. [1]
  Jing WU , Puzhen HUI , Huilin ZHENG , Pingchuan YUAN , Chunfei WANG , Hui WANG , Xiaoxia GU . Synthesis, crystal structures, and antitumor activities of transition metal complexes incorporating a naphthol-aldehyde Schiff base ligand. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2422-2428. doi: 10.11862/CJIC.20240278
2. [2]
  Ke QIAO , Yanlin LI , Shengli HUANG , Guoyu YANG . Advancements in asymmetric catalysis employing chiral iridium (ruthenium) complexes. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2091-2104. doi: 10.11862/CJIC.20240265
3. [3]
  Guojie Xu , Fang Yu , Yunxia Wang , Meng Sun . Introduction to Metal-Catalyzed β-Carbon Elimination Reaction of Cyclopropenones. University Chemistry, 2024, 39(8): 169-173. doi: 10.3866/PKU.DXHX202401060
4. [4]
  Geyang Song , Dong Xue , Gang Li . Recent Advances in Transition Metal-Catalyzed Synthesis of Anilines from Aryl Halides. University Chemistry, 2024, 39(2): 321-329. doi: 10.3866/PKU.DXHX202308030
5. [5]
  Pengzi Wang , Wenjing Xiao , Jiarong Chen . Copper-Catalyzed C―O Bond Formation by Kharasch-Sosnovsky-Type Reaction. University Chemistry, 2025, 40(4): 239-244. doi: 10.12461/PKU.DXHX202406090
6. [6]
  Jiaxun Wu , Mingde Li , Li Dang . The R eaction of Metal Selenium Complexes with Olefins as a Tutorial Case Study for Analyzing Molecular Orbital Interaction Modes. University Chemistry, 2025, 40(3): 108-115. doi: 10.12461/PKU.DXHX202405098
7. [7]
  Heng Zhang . Determination of All Rate Constants in the Enzyme Catalyzed Reactions Based on Michaelis-Menten Mechanism. University Chemistry, 2024, 39(4): 395-400. doi: 10.3866/PKU.DXHX202310047
8. [8]
  Xueting Cao , Shuangshuang Cha , Ming Gong . 电催化反应中的界面双电层：理论、表征与应用. Acta Physico-Chimica Sinica, 2025, 41(5): 100041-. doi: 10.1016/j.actphy.2024.100041
9. [9]
  Tao Cao , Fang Fang , Nianguang Li , Yinan Zhang , Qichen Zhan . Green Synthesis of p-Hydroxybenzonitrile Catalyzed by Spinach Extracts under Red-Light Irradiation: Research and Exploration of Innovative Experiments for Pharmacy Undergraduates. University Chemistry, 2024, 39(5): 63-69. doi: 10.3866/PKU.DXHX202309098
10. [10]
  Yuanpei ZHANG , Jiahong WANG , Jinming HUANG , Zhi HU . Preparation of magnetic mesoporous carbon loaded nano zero-valent iron for removal of Cr(Ⅲ) organic complexes from high-salt wastewater. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1731-1742. doi: 10.11862/CJIC.20240077
11. [11]
  Zhicheng JU , Wenxuan FU , Baoyan WANG , Ao LUO , Jiangmin JIANG , Yueli SHI , Yongli CUI . MOF-derived nickel-cobalt bimetallic sulfide microspheres coated by carbon: Preparation and long cycling performance for sodium storage. Chinese Journal of Inorganic Chemistry, 2025, 41(4): 661-674. doi: 10.11862/CJIC.20240363
12. [12]
  Yueguang Chen , Wenqiang Sun . “Carbon” Adventures. University Chemistry, 2024, 39(9): 248-253. doi: 10.3866/PKU.DXHX202308074
13. [13]
  Xuejie Wang , Guoqing Cui , Congkai Wang , Yang Yang , Guiyuan Jiang , Chunming Xu . 碳基催化剂催化有机液体氢载体脱氢研究进展. Acta Physico-Chimica Sinica, 2025, 41(5): 100044-. doi: 10.1016/j.actphy.2024.100044
14. [14]
  Yingchun ZHANG , Yiwei SHI , Ruijie YANG , Xin WANG , Zhiguo SONG , Min WANG . Dual ligands manganese complexes based on benzene sulfonic acid and 2, 2′-bipyridine: Structure and catalytic properties and mechanism in Mannich reaction. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1501-1510. doi: 10.11862/CJIC.20240078
15. [15]
  Ruitong Zhang , Zhiqiang Zeng , Xiaoguang Zhang . Improvement of Ethyl Acetate Saponification Reaction and Iodine Clock Reaction Experiments. University Chemistry, 2024, 39(8): 197-203. doi: 10.3866/PKU.DXHX202312004
16. [16]
  Xiangyu CAO , Jiaying ZHANG , Yun FENG , Linkun SHEN , Xiuling ZHANG , Juanzhi YAN . Synthesis and electrochemical properties of bimetallic-doped porous carbon cathode material. Chinese Journal of Inorganic Chemistry, 2025, 41(3): 509-520. doi: 10.11862/CJIC.20240270
17. [17]
  Kai CHEN , Fengshun WU , Shun XIAO , Jinbao ZHANG , Lihua ZHU . PtRu/nitrogen-doped carbon for electrocatalytic methanol oxidation and hydrogen evolution by water electrolysis. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1357-1367. doi: 10.11862/CJIC.20230350
18. [18]
  Shuying Zhu , Shuting Wu , Ou Zheng . Improvement and Expansion of the Experiment for Determining the Rate Constant of the Saponification Reaction of Ethyl Acetate. University Chemistry, 2024, 39(4): 107-113. doi: 10.3866/PKU.DXHX202310117
19. [19]
  Cunling Ye , Xitong Zhao , Hongfang Wang , Zhike Wang . A Formula for the Calculation of Complex Concentrations Arising from Side Reactions and Its Applications. University Chemistry, 2024, 39(4): 382-386. doi: 10.3866/PKU.DXHX202310043
20. [20]
  Lina Guo , Ruizhe Li , Chuang Sun , Xiaoli Luo , Yiqiu Shi , Hong Yuan , Shuxin Ouyang , Tierui Zhang . 层状双金属氢氧化物的层间阴离子对衍生的Ni-Al₂O₃催化剂光热催化CO₂甲烷化反应的影响. Acta Physico-Chimica Sinica, 2025, 41(1): 2309002-. doi: 10.3866/PKU.WHXB202309002

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(269)
HTML views(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