Citation: Ye Junwei, Huang Xueming, Wang Xiaoxiao, Zheng Ting, Gao Yuan, Gong Weitao, Ning Guiling. Research Progress on the Synthesis and Application of Cyclopentadiene Derivatives[J]. Chinese Journal of Organic Chemistry, ;2016, 36(6): 1299-1307. doi: 10.6023/cjoc201512012 shu

Research Progress on the Synthesis and Application of Cyclopentadiene Derivatives

1.
State Key Laboratory of Fine Chemicals and School of Chemical Engineering, Faculty of Chemical, Environmental and Biological Science and Technology, Dalian University of Technology, Dalian 116024

Corresponding author: Ye Junwei, junweiye@dlut.edu.cn Ning Guiling, ninggl@dlut.edu.cn
Received Date: 9 December 2015
Revised Date: 22 January 2016

Fund Project: Project supported by the National Natural Science Foundation of China Nos. 51003009, 20772014and the Fundamental Research Funds for the Central Universities of China No. DUT14LK32and the Science and Technology Research Foundation of Education Department of Liaoning Province No. L2014033

Figures(14)

Cyclopentadiene and its derivatives are a type of important small molecule cyclic olefin compounds, which have been widely applied in many fields such as synthesis of metallocene compounds, synthesis of organic intermediates and organic photoelectric materials. Based on our recent research results, in this review, the research progress on the synthesis of cyclopentadiene derivatives and the application of some typical cyclopentadiene derivatives in the field of organic synthesis are summarized.
- cyclopentadiene derivatives,
- synthesis,
- application,
- metallocene compounds,
- organic intermediates
1. [1]
  Tjahjono, A. M.; Feng, G.; Hermanto, M. W.; Cechao, F.; Garland, M. RSC Adv. 2014, 4, 22194.
2. [2]
  Feng, Y.-S.; Hao, J.; Liu, W.-W.; Yao, Y.-J.; Cheng, Y.; Xu, H.-J. Chin. Chem. Lett. 2015, 26, 709.
3. [3]
  Hoops, M. D.; Ault, B. S. J. Am. Chem. Soc. 2009, 131, 2853.
4. [4]
  Levandowski, B. J.; Houk, K. N. J. Org. Chem. 2015, 80, 3530.
5. [5]
  Desimoni, G.; Faita, G.; Toscanini, M.; Boiocchi, M. Chem. Eur. J. 2007, 13, 9478.
6. [6]
  McGivern, W. S.; Manion, J. A.; Tsang, W. J. Phys. Chem. A 2006, 110, 12822.
7. [7]
  Yang, C.; Cho, S.; Chiechi, R. C.; Walker, W.; Coates, N. E.; Moses, D.; Heeger, A. J.; Wudl, F. J. Am. Chem. Soc. 2008, 130, 16524.
8. [8]
  Suess-Fink, G. Dalton Trans. 2010, 39, 1673.
9. [9]
  Kim, H.; Choi, T.; Cha, M. C.; Chang, J. Y. J. Polym. Sci., Part A: Polym. Chem. 2013, 51, 3646.
10. [10]
  Rettenmeier, E.; Schuster, A. M.; Rudolph, M.; Rominger, F.; Gade, C. A.; Hashmi, A. S. K. Angew. Chem. Int. Ed. 2013, 52, 5880.
11. [11]
  Geng, W. Z.; Wang, C.; Guang, J.; Hao, W.; Zhang, W.-X.; Xi, Z. F. Chem. Eur. J. 2013, 19, 8657.
12. [12]
  Wirtanen, T.; Muuronen, M.; Melchionna, M.; Patzschke, M.; Helaja, J. J. Org. Chem. 2014, 79, 10269.
13. [13]
  Fang, Z. X.; Liu, J. Q.; Liu, Q.; Bi, X. H. Angew. Chem. Int. Ed. 2014, 53, 7209.
14. [14]
  Yang, L. J.; Ye, J. W.; Xu, L. F.; Yang, X. Y.; Gong, W. T.; Lin, Y.; Ning, G. L. RSC Adv. 2012, 2, 11529.
15. [15]
  Zhang, X. D.; Ye, J. W.; Xu, L. F.; Yang, L. J.; Deng, D.; Ning, G. L. J. Lumin. 2013, 139, 28.
16. [16]
  Ye, J. W.; Deng, D.; Gao, Y.; Wang, X. X.; Yang, L. J.; Lin, Y.; Ning, G. L. Spectrochim. Acta, Part A 2015, 134, 22.
17. [17]
  Ye, J.W.; Gao, Y.; He, L.; Tan, T. T.; Chen, W.; Liu, Y.; Wang, Y.; Ning, G. L. Dyes Pigm. 2016, 124, 145.
18. [18]
  Ye, J. W.; Xu, L. F.; Gao, Y.; Wang, H.; Ding, Y. Z.; Deng, D.; Gong, W. T.; Ning, G. L. Synth. Met. 2013, 175, 170.
19. [19]
  Ning, G. L.; Li, X. C.; Munakata, M.; Gong, W. T.; Maekawa, M.; Kamikawa, T. J. Org. Chem. 2004, 69, 1432.
20. [20]
  Gong, W. T.; Ning, G. L.; Li, X. C.; Wang, L.; Lin, Y. J. Org. Chem. 2005, 70, 5768.
21. [21]
  Yang, L. J.; Ye, J. W.; Gao, Y.; Deng,D.; Gong, W. T.; Li, Y.; Ning, G. L.; Tetrahedron Lett. 2013, 54, 2967.
22. [22]
  Ye, J. W.; Zhang, X. D.; Deng, D.; Ning, G. L.; Liu, T. Q.; Zhuang, M. L.; Yang, L. J.; Gong, W. T.; Lin, Y. RSC Adv. 2013, 3, 8232.
23. [23]
  Zhang, X. D.; Ye, J. W.; Wang, S. N.; Gong, W. T.; Lin, Y.; Ning, G. L. Org. Lett. 2011, 13, 3608.
24. [24]
  Yang, L. J.; Ye, J. W.; Gao, Y.; Deng, D.; Lin, Y.; Ning, G. L. Eur. J. Org. Chem. 2014, 515
25. [25]
26. [26]
27. [27]
  Li, G.; Gong, W.-T.; Ye, J.-W.; Lin, Y.; Ning, G.-L. Synth. Commun. 2012, 42, 480.
28. [28]
29. [29]
  Peng, S. Y.; Gao, T.; Sun, S. F.; Peng, Y. H.; Wu, M. H.; Guo, H. B.; Wang, J. Adv. Synth. Catal. 2014, 356, 319.
30. [30]
  Dömling, A. Chem. Rev. 2006, 106, 17.
31. [31]
  Chen, L.; Mahmoud, S. M.; Yin, X. D.; Lalancette, R. A.; Pietrangelo A. J. Am. Chem. Soc. 2013, 15, 5970.
32. [32]
  Loh, C. C. J.; Enders, D. Chem. Eur. J. 2012, 18, 10212.
33. [33]
  Becker, L.; Burlakov, V. V.; Arndt, P.; Spannenberg, A.; Baumann, W.; Jiao, H. J.; Rosenthal, U. Chem. Eur. J. 2013, 19, 4230.
34. [34]
  Kryukov, S. I.; Dzyuba, I. V.; Smirnov, V. A. Neftekhimiya 1991, 31, 386.
35. [35]
  Braga, A. A. C.; Morgon, N. H.; Ujaque, G.; Maseras, F. J. Am. Chem. Soc. 2005,127, 9298.
36. [36]
37. [37]
  Li, L.; Cai, Z.; Shen, B.; Xin, Z.; Ling, H. Chem. Eng. Technol. 2011, 34, 1468.
38. [38]
  Khambata, B. S.; Wassermann, A. J. Chem. Soc. 1939, 375.
39. [39]
  Krupka, J. Pet. Coal. 2010, 52, 290.
40. [40]
  Goswami, T.; Das, D. K.; Goswami, D. Chem. Phys. Lett. 2013, 558, 1.
41. [41]
  Herndon, W. C.; Grayson, C. R.; Manion, J. M. J. Org. Chem. 1967, 32, 526.
42. [42]
  Wang, W.; Chen, J.-G.; Song, L.-P.; Liu, Z.-T.; Liu, Z.-W.; Lu, J.; Xiao, J. L.; Hao, Z. P. Energy Fuels 2013, 27, 6339.
43. [43]
  Wang, W. T.; Cong, Y.; Chen, S.; Sun, C. X.; Wang, X. D.; Zhang, T. Top. Catal. 2015, 58, 350.
44. [44]
  Mendez, I. D.; Klimova, E.; Klimova, T.; Hernández, O. S.; Martínez, G. M. J. Organomet. Chem. 2003, 681, 115.
45. [45]
  Kollenz, G.; Ebner, S. Sci. Synth. 2006, 23, 271.
46. [46]
  Scheer, A. M.; Mukarakate, C.; Robichaud, D. J.; Nimlos, M. R.; Carstensen, H.-H.; Barney Ellison, G. J. Chem. Phys. 2012, 136, 044309.
47. [47]
  Koch, R.; Blanch, R. J.; Wentrup, C. J. Org. Chem. 2014, 79, 6978.
48. [48]
  Siemeling, U.; Neumann, B.; Stammler, H.-G.; Salmon, A. Z. Anorg. Allg. Chem. 2002, 628, 2315.
49. [49]
  Morris, D. M.; McGeagh, M.; De Peña, D.; Merola, J. S. Polyhedron 2014, 84, 120.
50. [50]
  Pal, R.; Mukherjee, S.; Chandrasekhar, S.; Guru Row, T. N. J. Phys. Chem. A 2014, 118, 3479.
51. [51]
  Kaleta, K.; Strehler, F.; Hildebrandt, A.; Beweries, T.; Arndt, P.; Rüffer, T.; Spannenberg, A.; Lang, H.; Rosenthal, U. Chem. Eur. J. 2012, 18, 12672.
52. [52]
  Mehdi, G.; Ali-Tabatabaei, G.; Maciej, K. J. Org. Chem. 2013, 78, 2611.
53. [53]
54. [54]
  Wu, X. J.; Zeng, X. C. J. Am. Chem. Soc. 2009, 131, 14246.
55. [55]
  Piper, T. S.; Wilkinson, G. J. Inorg. Nucl. 1956, 3(2), 104.
56. [56]
  Jiang, X. J.; Chen, L. M.; Wang, X.; Long, L.; Xiao, Z. Y.; Liu, X. M. Chem. Eur. J. 2015, 21, 13065.
57. [57]
  Loughrey, B. T.; Williams, M. L.; Carruthers, T. J.; Parsons, P. G.; Healy, P. C. Aust. J. Chem. 2010, 63, 245.
58. [58]
  Micallef, L. S.; Loughrey, B. T.; Healy, P. C.; Parsons, P. G.; Williams, M. L. Organometallics 2011, 30, 1395.
59. [59]
  Schaarschmidt, D.; Lang, H. Organometallics 2013, 32, 5668.
60. [60]
  Ogasawara, M.; Watanabe, S.; Nakajima, K.; Takahashi, T. J. Am. Chem. Soc. 2010, 132, 2136.
61. [61]
  Zheng, C.; You, S.-L. RSC Adv. 2014, 4, 6173.
62. [62]
  Siegel, S.; Schmalz, H.-G. Angew. Chem., Int. Ed. 1997, 36, 2456.
63. [63]
  Gao, D.-W.; Shi, Y.-C.; Gu, Q.; Zhao, Z.-L.; You, S.-L. J. Am. Chem. Soc. 2013, 135, 86.
64. [64]
  Pi, C.; Li, Y.; Cui, X. L.; Zhang, H.; Han, Y. B.; Wu, Y. J. Chem. Sci. 2013, 4, 2675.
65. [65]
  Pi, C.; Cui, X. L.; Liu, X. Y.; Guo, M. X.; Zhang, H. Y.; Wu, Y. J. Org. Lett. 2014, 16, 5164.
66. [66]
  Plate, A. F.; Stanko, V. I. Bull. Acad. Sci. USSR, Div. Chem. Sci. 1956, 5, 1173.
67. [67]
  Athawale, V. D.; Rathi, S. C. J. Appl. Polym. Sci. 1997, 66 , 1399.
68. [68]
  Fernando, C.-L.; Santiago, G.-Q.; Claudia, A.; Keane, M. A. Appl. Catal. A 2014, 473, 41.
69. [69]
  Shi, Y.; Wilmot, J. T.; Nordstrøm, L. U.; Tan, D. S.; Gin, D. Y. J. Am. Chem. Soc. 2013, 135,14313.
70. [70]
  Samoshin, A. V.; Hawker, C. J.; Read de Alaniz, J. ACS Macro. Lett. 2014, 3, 753.
71. [71]
  Bian, S.; Scott, A. M.; Cao, Y.; Liang, Y.; Osuna, S.; Houk, K. N.; Braunschweig, A. B. J. Am. Chem. Soc. 2013, 135, 9240.
72. [72]
  Kouznetsov, V. V. Tetrahedron 2009, 65, 2721.
73. [73]
  Gotoh, H.; Uchimaru, T.; Hayashi, Y. Chem. Eur. J. 2015, 21, 12337.
74. [74]
  Liu, J. H.; Lei, M.; Hu, L. H. Green Chem. 2012, 14, 2534.
75. [75]
  Jorner, K.; Emanuelsson, R.; Dahlstrand, C.; Tong, H.; Denisova, A. V.; Ottosson, H. Chem. Eur. J. 2014, 20, 9295.
76. [76]
  Sha, L.; Li, L.; Yuan, F. G. Chin. J. Chem. 2014, 32, 1214.
77. [77]
  Finke, A. D.; Diederich, F. Chem. Rec. 2015, 15, 19.
78. [78]
  Dahlstrand, C.; Rosenberg, M.; Kilså, K.; Ottosson, H. J. Phys. Chem. A 2012, 116, 5008.
79. [79]
  Alonso, M.; Herradón, B. Phys. Chem. Chem. Phys. 2010, 12, 1305.
80. [80]
  Müller, T. Angew. Chem., Int. Ed. 2002, 41, 2276.
81. [81]
  Xu, S. T.; Zheng, A.; Wei, Y. X.; Chen, J. R.; Li, J. Z.; Chu, Y. Y.; Zhang, M. Z.; Wang, Q. Y.; Zhou, Y.; Wang, J. B.; Deng, F.; Liu, Z. M. Angew. Chem., Int. Ed. 2013, 52, 11564.
82. [82]
  Nikolov, P.; Metzov, S. J. Photochem. Photobiol. A: Chem. 2000, 135, 13.
83. [83]
  Bello, A. M.; Kotra, L. P. Tetrahedron Lett. 2003, 44, 9271.
1. [1]
  Jiaming Xu , Yu Xiang , Weisheng Lin , Zhiwei Miao . Research Progress in the Synthesis of Cyclic Organic Compounds Using Bimetallic Relay Catalytic Strategies. University Chemistry, 2024, 39(3): 239-257. doi: 10.3866/PKU.DXHX202309093
2. [2]
  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
3. [3]
  Xinting XIONG , Zhiqiang XIONG , Panlei XIAO , Xuliang NIE , Xiuying SONG , Xiuguang YI . Synthesis, crystal structures, Hirshfeld surface analysis, and antifungal activity of two complexes Na(Ⅰ)/Cd(Ⅱ) assembled by 5-bromo-2-hydroxybenzoic acid ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1661-1670. doi: 10.11862/CJIC.20240145
4. [4]
  Yuanyin Cui , Jinfeng Zhang , Hailiang Chu , Lixian Sun , Kai Dai . Rational Design of Bismuth Based Photocatalysts for Solar Energy Conversion. Acta Physico-Chimica Sinica, 2024, 40(12): 2405016-. doi: 10.3866/PKU.WHXB202405016
5. [5]
  Tiantian Zheng , Huiyi Wang , Huimin Li , Xuanhe Liu , Hong Shang . Anti-Counterfeiting National Salvation Chronicle of 006. University Chemistry, 2024, 39(9): 254-258. doi: 10.3866/PKU.DXHX202307032
6. [6]
  Wenli FENG , Lu ZHAO , Yunfeng BAI , Feng FENG . Research progress on ultralong room temperature phosphorescent carbon dots. Chinese Journal of Inorganic Chemistry, 2025, 41(5): 833-846. doi: 10.11862/CJIC.20240308
7. [7]
  Miaomiao He , Zhiqing Ge , Qiang Zhou , Jiaqing He , Hong Gong , Lingling Li , Pingping Zhu , Wei Shao . Exploring the Fascinating Realm of Quantum Dots. University Chemistry, 2024, 39(6): 231-237. doi: 10.3866/PKU.DXHX202310040
8. [8]
  Laiying Zhang , Yaxian Zhu . Exploring the Silver Family. University Chemistry, 2024, 39(9): 1-4. doi: 10.12461/PKU.DXHX202409015
9. [9]
  Liang TANG , Jingfei NI , Kang XIAO , Xiangmei LIU . Synthesis and X-ray imaging application of lanthanide-organic complex-based scintillators. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1892-1902. doi: 10.11862/CJIC.20240139
10. [10]
  Chi Li , Jichao Wan , Qiyu Long , Hui Lv , Ying Xiong . N-Heterocyclic Carbene (NHC)-Catalyzed Amidation of Aldehydes with Nitroso Compounds. University Chemistry, 2024, 39(5): 388-395. doi: 10.3866/PKU.DXHX202312016
11. [11]
  Nan Xiao , Fang Sun . 二芳基硫醚化合物的构建及应用. University Chemistry, 2025, 40(6): 360-363. doi: 10.12461/PKU.DXHX202407099
12. [12]
  Aidang Lu , Yunting Liu , Yanjun Jiang . Comprehensive Organic Chemistry Experiment: Synthesis and Characterization of Triazolopyrimidine Compounds. University Chemistry, 2024, 39(8): 241-246. doi: 10.3866/PKU.DXHX202401029
13. [13]
  Yihao Zhao , Jitian Rao , Jie Han . Synthesis and Photochromic Properties of 3,3-Diphenyl-3H-Naphthopyran: Design and Teaching Practice of a Comprehensive Organic Experiment. University Chemistry, 2024, 39(10): 149-155. doi: 10.3866/PKU.DXHX202402050
14. [14]
  Qianlang Wang , Jijun Sun , Qian Chen , Quanqin Zhao , Baojuan Xi . The Appeal of Organophosphorus Compounds: Clearing Their Name. University Chemistry, 2025, 40(4): 299-306. doi: 10.12461/PKU.DXHX202405205
15. [15]
  Xinyu Zhu , Meili Pang . Application of Functional Group Addition Strategy in Organic Synthesis. University Chemistry, 2024, 39(3): 218-230. doi: 10.3866/PKU.DXHX202308106
16. [16]
  Jia-He Li , Yu-Ze Liu , Jia-Hui Ma , Qing-Xiao Tong , Jian-Ji Zhong , Jing-Xin Jian . 洛芬碱衍生物的合成、化学发光与重金属离子检测. University Chemistry, 2025, 40(6): 230-237. doi: 10.12461/PKU.DXHX202407080
17. [17]
  Tianyun Chen , Ruilin Xiao , Xinsheng Gu , Yunyi Shao , Qiujun Lu . Synthesis, Crystal Structure, and Mechanoluminescence Properties of Lanthanide-Based Organometallic Complexes. University Chemistry, 2024, 39(5): 363-370. doi: 10.3866/PKU.DXHX202312017
18. [18]
  Jingjing QING , Fan HE , Zhihui LIU , Shuaipeng HOU , Ya LIU , Yifan JIANG , Mengting TAN , Lifang HE , Fuxing ZHANG , Xiaoming ZHU . Synthesis, structure, and anticancer activity of two complexes of dimethylglyoxime organotin. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1301-1308. doi: 10.11862/CJIC.20240003
19. [19]
  Xilin Zhao , Xingyu Tu , Zongxuan Li , Rui Dong , Bo Jiang , Zhiwei Miao . Research Progress in Enantioselective Synthesis of Axial Chiral Compounds. University Chemistry, 2024, 39(11): 158-173. doi: 10.12461/PKU.DXHX202403106
20. [20]
  Jianfeng Yan , Yating Xiao , Xin Zuo , Caixia Lin , Yaofeng Yuan . Comprehensive Chemistry Experimental Design of Ferrocenylphenyl Derivatives. University Chemistry, 2024, 39(4): 329-337. doi: 10.3866/PKU.DXHX202310005

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(4697)
HTML views(1416)

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