Benzimidazoles-Containing Transition Metal Complexes: A Novel Catalyst for Ethylene Oligomerization and Polymerization

doi:10.6023/cjoc201405005

Chin. J. Org. Chem. ›› 2014, Vol. 34 ›› Issue (11): 2224-2235.DOI: 10.6023/cjoc201405005 Previous Articles Next Articles

苯并咪唑类过渡金属配合物: 新型乙烯齐聚与聚合催化剂

肖立伟, 李玲玲, 高红杰, 任萍, 寇伟, 时亚茹

廊坊师范学院化学与材料科学学院廊坊 065000

收稿日期:2014-05-05 修回日期:2014-06-06 发布日期:2014-07-02
通讯作者: 肖立伟,xiaoliwei2000@sina.com E-mail:xiaoliwei2000@sina.com
基金资助:
河北省自然科学基金(No.B2013408014)和廊坊师范学院重点基金(No.LSZZ201302)资助项目.

Benzimidazoles-Containing Transition Metal Complexes: A Novel Catalyst for Ethylene Oligomerization and Polymerization

Xiao Liwei, Li Lingling, Gao Hongjie, Ren Ping, Kou Wei, Shi Yaru

Faculty of Chemistry and Material Science, Langfang Teachers University, Langfang 065000

Received:2014-05-05 Revised:2014-06-06 Published:2014-07-02
Supported by:
Project supported by the Natural Science Foundation of Hebei Province (No.B2013408014) and the Key Foundation of Langfang Teachers University (No.LSZZ201302).

Benzimidazole heterocycles have good selectivity for coordination and can form a variety of metal complexes, which exhibit excellent biological, fluorescence and catalytic properties. In this paper, the progress for synthesis of benzimidazoles-containing transition metal complexes and their catalytic activity for ethylene oligomerization and polymerization are summarized, and the influence of the structural factor of complexes such as electronic effect and steric effect of substituent group on the catalytic performance is discussed.

Key words: benzimidazole, coordination catalysis, ethylene oligomerization and polymerization, structure-activity relationship

Cite this article

Xiao Liwei, Li Lingling, Gao Hongjie, Ren Ping, Kou Wei, Shi Yaru. Benzimidazoles-Containing Transition Metal Complexes: A Novel Catalyst for Ethylene Oligomerization and Polymerization[J]. Chin. J. Org. Chem., 2014, 34(11): 2224-2235.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] Britovsek, G. J. P.; Gibson, V. C.; Wass, D. F. Angew. Chem., Int. Ed. 1999, 38, 428.
[2] Rosalinda, C.; Angelina, F. P.; Edgar, M.; Fabiola, T.; Horacio, L. S.; Noráh, B, B. Coord. Chem. Rev. 2009, 253, 1979.
[3] Zhu, G. M.; Yang, L. Y.; Cui, D. M. Chin. J. Org. Chem. 2014, 34, 495 (in Chinese).(朱观明, 杨柳阳, 崔冬梅, 有机化学, 2014, 34, 495.)
[4] Sun, W. H.; Hao, P.; Zhang, S.; Shi, Q. S.; Zuo, W. W.; Tang, X. B. Organometallics 2007, 26, 2720.
[5] Small, B. L.; Brookhart, M.; Bennett, A. M. A. J. Am. Chem. Soc. 1998, 120, 4049.
[6] Britovsek, G. J. P.; Gibson, V. C.; Kimberley, B. S.; Maddox, P. J.; McTavish, S. J.; Solan, G. A.; White, A. J. P.; Williams, D. J. Chem. Commun. 1998, 849.
[7] Tomov, A. K.; Chirinos, J. J.; Jones, D. J.; Long, R. J.; Gibson, V. C. J. Am. Chem. Soc. 2005, 127, 10166.
[8] Britovsek, G. J. P.; Mastroianni, S.; Solan, G. A.; Baugh, S. P. D.; Redshaw, C.; Gibson, V. C.; White, A. J. P.; Williams, D. J.; Elsegood, M. R. J. Chem. Eur. J. 2000, 6, 2221.
[9] Chen, Y. J.; Hao, P.; Zuo, W. W.; Gao, K.; Sun, W. H. J. Organomet. Chem. 2008, 693, 1829.
[10] Xiao, L. W.; Zhang, M.; Sun, W. H. Chem. Res. Chin. Univ. 2011, 27, 228.
[11] Xiao, L. W.; Gao, R.; Zhang, M.; Li, Y.; Cao, X. P.; Sun, W. H. Organometallics 2009, 28, 2225.
[12] Zhang, L. P.; Hou, X. H.; Yu, J. G.; Chen, X.; Hao, X.; Sun, W. H. Inorg. Chim. Acta 2011, 379, 70.
[13] Hao, P.; Chen, Y. J.; Xiao, T. P. F.; Sun, W. H. J. Organomet. Chem. 2010, 695, 90.
[14] Sun, W. H.; Jie, S.; Zhang, S.; Zhang, W.; Song, Y.; Ma, H.; Chen, J.; Wedeking, K.; Fröhlich, R. Organometallics 2006, 25, 666.
[15] Zhang, M.; Hao, P.; Zuo, W. W.; Jie, S. Y.; Sun, W. H. J. Organomet. Chem. 2008, 693, 483.
[16] Zhang, S.; Sun, W. H.; Xiao, T.; Hao, X. Organometallics 2010, 29, 1168.
[17] Xiao, T. P. F.; Zhang, S.; Li, B. X.; Hao, X.; Redshaw, C.; Li, Y. S.; Sun, W. H. Polymer 2011, 52, 5803.
[18] Xiao, T. P. F.; Zhang, S.; Kehr, G.; Hao, X.; Erker, G.; Sun, W. H. Organometallics 2011, 30, 3658.
[19] Xiao, T. P. F.; Hao, P.; Kehr, G.; Hao, X.; Erker, G.; Sun, W. H. Organometallics 2011, 30, 4847.
[20] Tarte, N. H.; Woo, S. I.; Cui, L. Q.; Gong, Y. D.; Hwang, Y. H. J. Organomet. Chem. 2008, 693, 729.
[21] Hao, P.; Zhang, S.; Sun, W. H.; Shi, Q. S.; Adewuyi, S.; Lu, X. M.; Li, P. Z. Organometallics 2007, 26, 2439.
[22] Xiao, L. W.; Zhang, M.; Gao, R.; Cao, X. P.; Sun, W. H. Aust. J. Chem. 2010, 63, 109.
[23] Chen, X.; Zhang, L. P.; Yu, J. G.; Hao, X.; Liu, H.; Sun, W. H. Inorg. Chim. Acta 2011, 370, 156.
[24] Zhang, M.; Zhang, S.; Hao, P.; Jie, S. Y.; Sun, W. H.; Li, P. Z.; Lu, X. M. Eur. J. Inorg. Chem. 2007, 3816.
[25] Wang, K. F.; Shen, M.; Sun, W. H. Dalton Trans. 2009, 4085.
[26] Wang, K. F.; Gao, R.; Hao, X.; Sun, W. H. Catal. Commun. 2009, 10, 1730.
[27] He, F.; Hao. X.; Cao, X. P.; Redshaw, C.; Sun, W. H. J. Organomet. Chem. 2012, 712, 46.
[28] Du, J. L.; Li, L. J.; Li, Y. F. Inorg. Chem. Commun. 2005, 8, 246.
[29] Shi, Q. S.; Zhang, S.; Chang, F.; Hao, P.; Sun, W. H. C. R. Chim. 2007, 10, 1200.
[30] Tarte, N. H.; Cho, H. Y.; Woo, S. I. Macromolecules 2007, 40, 8162.
[31] Liu, H.; Zhang, L. P.; Chen, L. Q.; Redshaw, C.; Li, Y.; Sun, W. H. Dalton Trans. 2011, 40, 2614.
[32] Tomov, A. K.; Gibson, V. C.; Britovsek, G. J. P.; Long, R. J.; Martin van, M.; Jones, D. J.; Tellmann, K. P.; Chirinos, J. J. Organometallics 2009, 28, 7033.
[33] Tomov, A. K.; Chirinos, J. J.; Long, R. J.; Gibson, V. C.; Elsegood, M. R. J. J. Am. Chem. Soc. 2006, 128, 7704.
[34] Zhang, W. J.; Sun, W. H.; Zhang, S.; Hou, J. X.; Wedeking, K.; Schultz, S.; Fröhlich. R.; Song, H. B. Organometallics 2006, 25, 1961.
[35] Chen, Y. J.; Zuo, W. W.; Hao, P.; Zhang, S.; Gao, K.; Sun, W. H. J. Organomet. Chem. 2008, 693, 750.
[36] Xiao, L. W.; Zhang, M.; Sun, W. H. Polyhedron 2010, 29, 142.
[37] Wang, D.; Liu, S. F.; Zeng, Y. N.; Sun, W. H.; Redshaw, C. Organometallics 2011, 30, 3001.
[38] Zaher, D.; Tomov, A. K.; Gibson, V. C.; White, A. J. P. J. Organomet. Chem. 2008, 693, 3889.
[39] Liu, S. F.; Zuo, W. W.; Zhang, S.; Hao, P.; Wang, D.; Sun, W. H. J. Polym. Sci., Part A: Polym. Chem. 2008, 46, 3411.
[40] Huang, W.; Zhang, W. J.; Sun, W. H. Polym. Bull. 2011, 10, 63 (in Chinese).(黄伟, 张文娟, 孙文华, 高分子通报, 2011, 10, 63.)
[41] Zuo, W. W.; Zhang, S.; Liu, S. F.; Liu, X. J.; Sun, W. H. J. Polym. Sci., Part A: Polym. Chem. 2008, 46, 3396.
[42] Zuo, W. W.; Zhang, M.; Sun, W. H. J. Polym. Sci., Part A: Polym. Chem. 2009, 47, 357.
[43] Liu, S. F.; Yi, J. J.; Zuo, W. W.; Wang, K. F.; Wang, D.; Sun, W. H. J. Polym. Sci., Part A: Polym. Chem. 2009, 47, 3154.
[44] Sun, W. H.; Liu, S. F.; Zhang, W. J.; Zeng, Y. N.; Wang, D.; Liang, T. L. Organometallics 2010, 29, 732.
[45] Stibrany, R. T.; Schulz, D. N.; Kacker, S.; Patil, A. O.; Baugh, L. S.; Rucker, S. P.; Zushma, S.; Berluche, E.; Sissano, J. A. Macromolecules 2003, 36, 8584.
[46] Baugh, L. S.; Sissano, J. A.; Kacker, S.; Berluche, E.; Stibrany, R. T.; Schulz, D. N.; Rucker, S. P. J. Polym. Sci., Part A: Polym. Chem. 2006, 44, 1817.
[47] Xiao, L. W.; Jing, X. M.; Kong, J. Chin. J. Org. Chem. 2013, 33, 1828 (in Chinese).(肖立伟, 景学敏, 孔洁, 有机化学, 2013, 33, 1828.)

苯并咪唑类过渡金属配合物: 新型乙烯齐聚与聚合催化剂

Benzimidazoles-Containing Transition Metal Complexes: A Novel Catalyst for Ethylene Oligomerization and Polymerization

PDF

Knowledge

Cited

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Haibo Huo, Guixia Li, Shijun Wang, Chun Han, Baojun Shi, Jian Li. Novel γ-Carboline Derivatives as Antibacterial Agents: Synthesis and Antibacterial Evaluation [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 204-215.
[2]	Mengjia Xiao, Xike Gao. Design, Synthesis and Anti-inflammatory Activity of Azulene Derivatives Containing Benzimidazole Unit [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3246-3256.
[3]	Xin Zuo, Shinuo Xu, Zhongyang Chen, Jianfeng Yan, Yaofeng Yuan. Research Progress of Electron Transport Properties in Ferrocene- Containing Single-Molecule Junctions [J]. Chinese Journal of Organic Chemistry, 2023, 43(7): 2313-2322.
[4]	Jinyan He, Fuyun Tian, Qingqing Wu, Yueming Zheng, Yuting Chen, Haiyan Xu, Zhengsheng Jin, Li Zhan, Xinqiang Cheng, Yueling Gu, Zhaobing Gao, Guilong Zhao. Design, Synthesis and Bioactivity of [3.3.3]Propellane-Based Voltage-Gated Calcium Channel α2δ Subunit Ligands [J]. Chinese Journal of Organic Chemistry, 2023, 43(6): 2226-2238.
[5]	Xingzhou Liu, Mingjia Yu, Jianhua Liang. Research Progress on the Synthesis of Protoberberine Skeleton and Its Anti-inflammatory Activity [J]. Chinese Journal of Organic Chemistry, 2023, 43(4): 1325-1340.
[6]	Rong Zhang, Xiang Gao, Lingling Chen, Fajun Nan. Discovery and Structure-Activity Relationship Studies of Thiazole- Oxazole Tandem Heterocyclic RNA Splicing Inhibitors [J]. Chinese Journal of Organic Chemistry, 2022, 42(9): 2925-2939.
[7]	Binghan Lin, Jibin Zhuo, Caixia Lin, Yong Gao, Yaofeng Yuan. Synthesis and Nucleotide Recognition Properties of Carborane-Based Benzoimidazolium Cyclophane [J]. Chinese Journal of Organic Chemistry, 2022, 42(8): 2551-2558.
[8]	Jing Zhao, Zhe Jin, Run Wang, Xin'geng Zhang, Yingmei Han, Chun Hu, Xiaoping Liu, Chuanming Zhang, Liping Jin. Design, Synthesis and Anticancer Activity of 2-((Pyridin- 2-ylmethyl)thio)-1H-benzimidazole Derivatives [J]. Chinese Journal of Organic Chemistry, 2022, 42(7): 2172-2183.
[9]	Ming Cai, Liang Shao, Fan Yang, Jihong Zhang, Fei Yu. Design, Synthesis of Pentacyclic Triterpenoid Glucose Conjugate and in vitro Activity against Influenza Virus [J]. Chinese Journal of Organic Chemistry, 2022, 42(5): 1453-1462.
[10]	Siyu Zhu, Xinyu Huo, Qin Ma, Wei Chen, Jie Zhang, Liang Guo. Design, Synthesis, and Antitumor Activity of β-Carboline-Benzimidazole Hybrids [J]. Chinese Journal of Organic Chemistry, 2022, 42(4): 1129-1135.
[11]	Yuanfang Kong, Bin Yang, Yan Zhuang, Jingyu Zhang, Demei Sun, Chunhong Dong. Research Progress on the Synthesis and Structure-Activity Relationship of Five Hypoglycemic Active Heterocycles Based on Dipeptidyl Peptidase 4 (DPP-4) Target Design [J]. Chinese Journal of Organic Chemistry, 2022, 42(3): 770-784.
[12]	Yan Zeng, Lifei Nie, Chao Niu, Aytilla Mamatjan, Khurshed Bozorov, Jiangyu Zhao, Haji Akber Aisa. Synthesis and Biological Activities of Dihydrooxazolo[5,4-d]-pyrrolo[1,2-a]pyrimidinones [J]. Chinese Journal of Organic Chemistry, 2022, 42(2): 543-556.
[13]	Wei Wang, Furan Wu, Yidan Ma, Dan Xu, Gong Xu. Study on Synthesis and Antifungal Activity of Novel Benzamides Containing Substituted Pyrazole Unit [J]. Chinese Journal of Organic Chemistry, 2022, 42(2): 607-618.
[14]	Xiaojing Tian, Zhenzhen Fan, Si Jiang, Zhiwei Li, Jiangsheng Li, Yuefei Zhang, Cuihong Lu, Weidong Liu. Metal-Free Synthesis of Benzimidazo[1,2-c]quinazolines from N-Cyanobenzimidazoles via Double C—H Functionalizations [J]. Chinese Journal of Organic Chemistry, 2022, 42(11): 3684-3692.
[15]	Yuyu Guo, Xiangjie Chen, Shiwu Li, Zhihua Cai, Lin He. Synthesis of Mutisubstituted Dihydropyridino[1,2-a]benzimidazole Derivatives via Tandem Reaction of 2-Arylbenzimidazoles [J]. Chinese Journal of Organic Chemistry, 2021, 41(9): 3692-3700.