Citation: Su Biyun, Jia Peiyu, Wang Yanzhao, Li Yaning, Huang He, Li Qianding. Copolymerization of Ethylene/Polar Monomer Catalyzed by Phosphinoarenesulfonate (PO) Metal Catalysts and the Catalytic Mechanism[J]. Chinese Journal of Organic Chemistry, ;2016, 36(10): 2344-2352. doi: 10.6023/cjoc201603048 shu

Copolymerization of Ethylene/Polar Monomer Catalyzed by Phosphinoarenesulfonate (PO) Metal Catalysts and the Catalytic Mechanism

Su Biyun ^a,*,, ,
Jia Peiyu ^b ,
Wang Yanzhao ^a ,
Li Yaning ^a ,
Huang He ^a ,
Li Qianding ^a

a.
College of Chemistry and Chemical Engineering, Xi'an Shiyou University, Xi'an 710065
b.
Ningbo Exciton Technology, Co., Ltd., Ningbo 315100

Corresponding author: Su Biyun, subiyun@xsyu.edu.cn.
Received Date: 30 March 2016
Revised Date: 11 May 2016

Fund Project: ProjectProject of Shaanxi Education Department No.12JK0620and the Science and Technology Research Program of Shaanxi Province No.2013 KJXX-33

Figures(2)

The metal catalysts based on phosphinoarenesulfonate (PO) ligand display interesting olefin polymerization prop-erties, which not only polymerize ethylene to linear polyethylene, but also copolymerize ethylene with polar vinyl monomers or CO to functional linear copolymers. The structural features of PO ligand and the novel polymerization reactions initiated by (PO)Pd(Ⅱ) complexes are assumed. Then the application of (PO)Ni(Ⅱ) catalysts in the copolymerization of ethylene with polar monomers, as well as the rare catalytic properties of Pd(Ⅱ), Ru(Ⅳ) catalysts based on phosphine-bis(arenesulfonate) (OPO) ligands are reviewed. At last, the influence of PO ligand structural features such as symmetry, flexibility, steric effect in axial direction, as well as the pure electronic effect on the insertion and polymerization reactivity of PO metal catalyst are explored, at the same time, the catalytic reaction mechanism is also studied.
- olefin/polar monomer copolymerization,
- phosphinoarenesulfonate ligand,
- Pd(Ⅱ), Ni(Ⅱ), Ru(IV) catalyst,
- catalytic mechanism
1. [1]
2. [2]
  Nakamura, A.; Ito, S, Nozaki, K. Chem. Rev. 2009, 109, 5215.
3. [3]
  Berkefeld, A.; Mecking, S. Angew. Chem., Int. Ed. 2008, 47, 2538.
4. [4]
  Ito, S.; Nozaki, K. Chem. Rec. 2010, 10, 315.
5. [5]
  Chung, T. C. Functionalization of Polyolefins, Academic Press, USA, 2002, p. 69.
6. [6]
  Osakada, K. Organometallic Reactions and Polymerization, Lecture Notes in Chemistry, Springer-Verlag, Berlin Heidelberg, 2014.
7. [7]
  Desurmont, G.; Tokimitsu, T.; Yasuda, H. Macromolecules 2000, 33(21), 7679.
8. [8]
  Johnson, L. K.; Killian, C. M.; Brookhart, M. J. Am. Chem. Soc. 1995, 117, 6414.
9. [9]
  Contrella, N. D.; Sampson, J. R.; Jordan, R. F. Organometallics 2014, 33, 3546.
10. [10]
  Ittel, S. D.; Johnson, L. K.; Brookhart, M. Chem. Rev. 2000, 100, 1169.
11. [11]
  Mecking, S.; Johnson, L. K.; Wang, L.; Brookhart, M. J. Am. Chem. Soc. 1998, 120, 888.
12. [12]
  Hou, Z. M.; Luo, Y. J.; Li, X. F. J. Organomet. Chem. 2006, 691(14), 3114.
13. [13]
  Yamamoto, A.; Nishiura, M.; Oyamada, J.; Koshino, H.; Hou, Z. M. Macromolecules 2016, 49(7), 2458.
14. [14]
  Kang, X. H.; Zhou, G. L.; Wang, X. B.; Qu, J. P.; Hou, Z. M.; Luo, Y. Organometallics 2016, 35(6), 913.
15. [15]
  Soller, B. S.; Sun, Q.; Salzinger, S.; Jandl, C.; Pöthig, A.; Rieger, B. Macromolecules 2016, 49(5), 1582.
16. [16]
  Wang, Z. C.; Liu, D. T.; Cui, D. M. Macromolecules 2016, 49(3), 781.
17. [17]
  Kuhn, P.; Semeril, D.; Matt, D.; Chetcuti, M. J.; Lutz, P. Dalton. Trans. 2007, 515.
18. [18]
  Murray, R. E.; Charleston, W. V. US 4689437, 1987[Chem. Abstr. 1988, 108, 6646].
19. [19]
  Murray, R. E.; Wenzel, T. T. Am. Chem. Soc. Div. Pet. Chem. 1989, 34, 599.
20. [20]
  Drent, E.; Van, D. R.; Van, G. R.; Van, O. B.; Pugh, R. I. Chem. Commun. 2002, 744.
21. [21]
  Drent, E.; Van, D. R.; Van, G. R.; Van, O. B.; Pugh, R. I. Chem. Commun. 2002, 964.
22. [22]
  Hearley, A. K.; Nowack, R. J.; Rieger, B. Organometallics 2005, 24, 2755.
23. [23]
  Kochi, T.; Yoshimura, K.; Nozaki, K. Dalton. Trans. 2006, 25.
24. [24]
  Kryuchkov, V. A.; Daigle, J. C.; Skupov, K. M.; Winnik, F. M.; Claverie,J. P. J. Am. Chem. Soc. 2010, 132, 15573.
25. [25]
  Friedberger, T.; Wucher, P.; Mecking, S. J. Am. Chem. Soc. 2012, 134, 1010.
26. [26]
  Runzi, T.; Frohlich, D.; Mecking, S. J. Am. Chem. Soc. 2014, 132, 17690.
27. [27]
  Daigle, J. C.; Piche, L. C.; Claverie, J. P. Macromolecules 2011, 44, 1760.
28. [28]
  Shen, Z. L.; Jordan, R. F. Macromolecules 2010, 43, 8706.
29. [29]
  Luo, S. J.; Vela, J.; Lief, G. R.; Jordan, R. F. J. Am. Chem. Soc. 2007, 129, 8946.
30. [30]
  Skupov, K. M.; Piche, L.; Claverie, J. P. Macromolecules 2008, 41, 2309.
31. [31]
  Bouilhac, C.; Runzi, T.; Mecking, S. Macromolecules 2010, 43, 3589.
32. [32]
  Nakamura, A.; Anselment, T. M. J.; Claverie. J. P.; Goodall, B.; Jordan, R. F.; Mecking, S.; Rieger, B.; Sen, A.; Leeuwen, P. W. N. M.; Nozaki, K. Acc. Chem. Res. 2013, 46(7), 1438.
33. [33]
  Guironnet, D.; Roesle, P.; Rünzi, T.; Göttker-Schnetmann, I.; Mecking, S. J. Am. Chem. Soc. 2009, 131, 422.
34. [34]
  Berkefeld, A.; Guironnet, D.; Neuwald, B.; Roesle, P.; Rünzi, T.; Wucher, P.; Göttker-Schnetmann, I.; Dürr, C.; Mecking, S. Polym. Prepr. 2010, 51(2), 367.
35. [35]
  Matthew, P. C.; Richard, F. J. Angew. Chem., Int. Ed. 2011, 50, 3744.
36. [36]
  Albietz, P. J.; Cleary, B. P.; Paw, W.; Eisenberg, R. Inorg. Chem. 2002, 41, 2095.
37. [37]
  Casares, J. A.; Espinet, P. Inorg. Chem. 1997, 36, 5428.
38. [38]
  Carrow, B. P.; Nozaki, K. J. Am. Chem. Soc. 2012, 134, 8820.
39. [39]
  Wilkes, C. E.; Daniels, C. A.; Summers, J. W. PVC Handbook, Carl Hanser Verlag, Munich, 2005.
40. [40]
  Boone, H. W.; Athey, P. S.; Mullins, M. J.; Philipp, D.; Muller, R.; Goddard, W. A. J. Am. Chem. Soc. 2002, 124, 8790.
41. [41]
  Philipp, D. M.; Muller, R. P.; Goddard, W. A.; Storer, J.; McAdon, M.; Mullins, M. J. Am. Chem. Soc. 2002, 124, 10198.
42. [42]
  Foley, S. R.; Stockland, R. A.; Shen, H. J.; Jordan, R. F. J. Am. Chem. Soc. 2003, 125, 4350.
43. [43]
  Nozaki, K.; Carrow, B. P. J. Am. Chem. Soc. 2012, 134, 8802.
44. [44]
  Leicht, H.; Göttker-Schnetmann, I.; Mecking, S. Angew. Chem., Int. Ed. 2013, 52, 3963.
45. [45]
  Zhang, D.; Guironnet, D.; Göttker-Schnetmann, I.; Mecking, S. Organometallics 2009, 28, 4072.
46. [46]
  Perrotin, P.; McCahill, J. S. J.; Wu, G.; Scott, L. S. Chem. Commun. 2011, 47, 6948.
47. [47]
  Barder, T. E.; Walker, S. D.; Martinelli, J. R.; Buchwald, S. L. J. Am. Chem. Soc. 2005, 127, 4685.
48. [48]
  Surry, D. S.; Buchwald, S. L. Angew. Chem., Int. Ed. 2008, 47, 6338.
49. [49]
  Zhou, X. Y.; Bontemps, S.; Jordan, R. F. Organometallics 2008, 27(19), 4822.
50. [50]
  Nowack, J. R.; Hearley, K. A.; Rieger, B. Z. Anorg. Allg. Chem. 2005, 631, 2775.
51. [51]
  Guironnet, D.; Runzi, T.; Göttker-Schnetmann, I.; Mecking, S. Med. Chem. Commun. 2008, 4965.
52. [52]
  Contrella, N. D.; Sampson, J. R.; Jordan, R. F. Organometallics 2014, 33, 3546.
53. [53]
  Shen, Z,; Jordan, R. F. J. Am. Chem. Soc. 2010, 132, 52.
54. [54]
  Mecking, S.; Johnson, L. K.; Wang, L.; Brookhart, M. J. Am. Chem. Soc. 1998, 120, 888.
55. [55]
  Kuwabara, J.; Tekeuchi, D.; Osakada, K. Chem. Commun. 2006, 3815.
56. [56]
  Rodriguez, B. A.; Delferro, M.; Marks, T. J. J. Am. Chem. Soc. 2009, 131, 5902.
57. [57]
  Shen, Z. L.; Jordan, R. F. Macromolecules 2010, 43, 8706.
58. [58]
  Carrow, B. P.; Nozaki, K. Macromolecules 2014, 47(8), 2541.
59. [59]
  Friedberger, T.; Ziller, J. W.; Guan, Z. B. Organometallics 2014, 33, 1913.
60. [60]
  Neuwald, B.; Falivene, L.; Caporaso, L.; Cavallo, L.; Mecking, S. Chem. Eur. J. 2013, 19, 17773.
61. [61]
  Neuwald, B.; Caporaso, L.; Cavallo, L.; Mecking, S. J. Am. Chem. Soc. 2013, 135, 1026
62. [62]
  Anselment, T. M. J.; Wichmann, C.; Anderson, C. E.; Herdtweck, E.; Rieger, B. Organometallics 2011, 30, 6602.
63. [63]
  Wucher, P.; Goldbach, V.; Mecking, S. Organometallics 2013, 32, 4516.
64. [64]
  Rünzi, T.; Tritschler, U.; Roesle, P.; Göttker-Schnetmann, I.; Möller, H. M.; Caporaso, L.; Poater, A.; Cavallo, L.; Mecking, S. Organometallics 2012, 31, 8388.
65. [65]
  Guo, L. H.; Dai, S. Y.; Sui, X. L.; Chen, C. L. ACS Catal. 2016, 6(1), 428.
66. [66]
  Ito, S.; Wang, W. H.; Nozaki, K. Polym. J. 2015, 47, 474.
67. [67]
  Jian, Z. B.; Falivene, L.; Wucher, P.; Roesle, P.; Caporaso, L.; Cavallo, L.; Inigo G., S.; Mecking, S. J. Chem. Eur. 2015, 21, 2062.
68. [68]
  Labed, A.; Jiang, F.; Labed, I.; Lator, A.; Peters, M.; Achard, M.; Kabouche, A.; Kabouche, Z.; Sharma, G. V. M.; Bruneau, C. ChemCatChem 2015, 7, 1090.
69. [69]
  Li, M. L.; Song; H. B.; Wang, B. Q. Organometallics 2015, 34(10), 1969.
70. [70]
  Nakano, R.; Nozaki, K. J. Am. Chem. Soc. 2015, 137(34), 10934.
71. [71]
  Schuster, N.; Rünzi, T.; Mecking, S. Macromolecules 2016, 49(4), 1172.
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