Late Transition Metal Complexes for Olefin Copolymerization with Polar Monomers

doi:10.6023/cjoc202009008

Abstract

Incorporation of small amounts of polar functional groups into non-polar polyolefins can dramatically improve properties of polyolefins. The development of late transition metal complexes for olefin copolymerization with polar monomers according to different types of complexes in the last decade is reviewed. With regard to α-diimine, phosphino-phenolate, salicylaldimine, ketoamine, phosphine-sulfonate, bisphospnine monoxide, N-heterocyclic carbene complexes and more emerging catalysts, fine modulation of key copolymerization parameters (activity, molecular weight, polar monemer incorporation, etc.) and material properties of polyolefins in a controlled way are described in detail. Despite many recent advances and enticing characteristics of these catalysts, there still remains challenges for industrial and commercial application due to a variety of limitations. To overcome some of these challenges, a brief outlook on the future of issues should be focused on is provided.

Key words: catalyst, polymerization, complex, olefin, polar monomer, late transition metal

Cite this article

Yongqing Li, Fan Wang, Yucai Cao. Late Transition Metal Complexes for Olefin Copolymerization with Polar Monomers[J]. Chinese Journal of Organic Chemistry, 2021, 41(4): 1396-1433.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

Fig. & Tab. 20

Scheme 1. Approaches for synthesis of polyolefins containing polar group

Scheme 2. General mechanism for late transition metal catalyzed ethylene copolymerization with polar monomer and “chain walking”

Figure 1. Late transition metal catalysts with various backbones for olefin copolymerization with polar monomers

Scheme 3. Polar monomer problem

Figure 2. Polar vinyl monomers

Figure 3. Polar allyl monomers and monomers with methylene spacers

Figure 4. Polar norbornyl monomers

Scheme 4. Mechanism for copolymerization catalyzed by 7

Scheme 5. Possibile mechanism for copolymerization of ethylene and allyl acrylate

Scheme 6. Possibile mechanism for copolymerization of ethylene and acrylic anhydride

Figure 5. Commercial polar copolymers

Figure 6. Copolymers of ethylene and polar monomers with different microstructures

Scheme 7. Polar-substituted polyethylene elastomers from ethylene copolymerization with polar monomers

Figure 7. Plots of hysteresis experiments of ten cycles at a strain of 300% for copolymer samples Reprinted (adapted) with permission from Ref. [200]. Copyright (2020) American Chemical Society

Figure 8. Stress vs strain curves for the polymer and copolymer products generated using 52 and 241 (a~c)241, (d) 52. Reprinted (adapted) with permission from Ref. [65]. Copyright (2018) American Chemical Society

Figure 9. Water contact angles of the polyethylene and copolymer products generated using 52 and 241 (a) 52, (b) 241. Reprinted (adapted) with permission from Ref. [65]. Copyright (2018) American Chemical Society

Scheme 8. Comonomers used in the copolymerization of ethylene

Figure 10. Thermal gravimetric analysis (TGA) curves and heat release rate (HRR) curves TGA curves of the copolymers (a) and terpolymers (b), HRR curves of copolymers (c) and terpolymers (d). Reproduced from Ref. [7c] with permission from The Royal Society of Chemistry.

Figure 11. Scanning electron microscope (SEM) images (a) PE/APP (m∶m=70∶30) and (b) PE/poly(E-co-O1)/APP (m∶m∶m=60∶10∶30) composites. Reproduced from Ref. [7c] with permission from The Royal Society of Chemistry.

Figure 12. Modulation of material properties through ENB incorporation, hydrogen bonding, Fe3+-induced crosslinking and sulfur-induced vulcanization

References 201

[1]	(a) Hlatky, G.G. Coord. Chem. Rev. 2000, 199,235. pmid: 11749267
	(b) Severn, J.R.; Chadwick, J.C.; Duchateau, R.; Friederichs, N. Chem. Rev. 2005, 105,4073. doi: 10.1021/cr040670d pmid: 11749267
	(c) Hlatky, G.G. Chem. Rev. 2000, 100,1347. pmid: 11749267
	(d) Chen, E.Y. X. Chem. Rev. 2009, 109,5157. pmid: 11749267
[2]	Coates, G.W. Chem. Rev. 2000, 100,1223.
[3]	Gibson, V.C.; Spitzmesser, S.K. Chem. Rev. 2003, 103,283. pmid: 12517186
[4]	Makio, H.; Terao, H.; Iwashita, A.; Fujita, T. Chem. Rev. 2011, 111,2363.
[5]	Ittel, S.D.; Johnson, L.K.; Brookhart, M. Chem. Rev. 2000, 100,1169. pmid: 11749263
[6]	(a) Chen, Z.K.; Mao, Y.H.; Cao, Y.C.; Liang, S.B.; Song, S.; Ni, C.; Liu, Z.Y.; Ye, X.F.; Shen, A.; Zhu, H.P. Chin. J. Org. Chem. 2018, 38,2937. (in Chinese)
	( 陈志康, 毛远洪, 曹育才, 梁胜彪, 宋莎, 倪晨, 刘振宇, 叶晓峰, 沈安, 朱红平, 有机化学, 2018, 38,2937.)
	(b) Liu, R.; Xiao, S.M.; Zhong, X.H.; Cao, Y.C.; Liang, S.B.; Liu, Z.Y.; Ye, X.F.; Shen, A.; Zhu, H.P. Chin. J. Org. Chem. 2015, 35,1861. (in Chinese)
	( 刘睿, 肖树萌, 钟向宏, 曹育才, 梁胜彪, 刘振宇, 叶晓峰, 沈安, 朱红平, 有机化学, 2015, 35,1861.)
	(c) Li, B.G.; Zhang, M.X.; Liu, W.F.; Wang, W.J. Chem. Ind. Eng. Prog. 2017, 36,3135. (in Chinese)
	( 李伯耿, 张明轩, 刘伟峰, 王文俊, 化工进展, 2017, 36,3135.)
[7]	(a) Zou, C.; Chen, C. Angew. Chem., Int. Ed. 2020, 59,395.
	(b) Na, Y.; Chen, C. Angew. Chem., Int. Ed. 2020, 59,7953.
	(c) Gao, J.X.; Cai, W.; Hu, Y.; Chen, C.L. Polym. Chem. 2019, 10,1416.
	(d) Takano, S.; Takeuchi, D.; Osakada, K.; Akamatsu, N.; Shishido, A. Angew. Chem., Int. Ed. 2014, 53,9246.
	(e) Yao, H.L.; He, X.H.; Chen, L.; Chen, Y.W.; Chen, D.F. J. Appl. Polym. Sci. 2013, 128,3540.
	(f) Rünzi, T.; Mecking, S. Adv. Funct. Mater. 2014, 24,387.
[8]	(a) Novák, I.; Borsig, E.; Hrčková, L.U.; Fiedlerová, A.; Kleinová, A.; Pollák, V. Polym. Eng. Sci. 2007, 47,1207.
	(b) Dai, S.Y.; Zhou, S.X.; Zhang, W.; Chen, C.L. Macromolecules 2016, 49,8855.
[9]	(a) Mazzolini, J.; Boyron, O.; Monteil, V.; Gigmes, D.; Bertin, D.; D’agosto, F.; Boisson, C. Macromolecules 2011, 44,3381.
	(b) Boaen, N.K.; Hillmyer, M.A. Chem. Soc. Rev. 2005, 34,267.
[10]	Wu, H.T.; Lv, C.; Jiang, T.; Cui, K.; Ma, Z. Chem. Ind. Eng. Prog. 2015, 34,1699. (in Chinese)
	( 吴昊天, 吕弛, 姜涛, 崔崑, 马志, 化工进展, 2015, 34,1699.)
[11]	Franssen, N.M. G.; Reek, J.N. H.; De Bruin, B. Chem. Soc. Rev. 2013, 42,5809.
[12]	(a) Shanmugam, S.; Boyer, C. Science 2016, 352,1053.
	(b) Parkatzidis, K.; Wang, H.S.; Truong, N.P.; Anastasaki, A. Chem 2020, 6,1575.
	(c) Tasdelen, M.A.; Kahveci, M.U.; Yagci, Y. Prog. Polym. Sci. 2011, 36,455.
	(d) Zhang, H.C.; Liu, Z.N.; Xi, F.F.; Li, Y.M.; Kong, L.; Hao, A.Y. Chin. J. Org. Chem. 2011, 31,1761. (in Chinese)
	( 张华承, 刘召娜, 辛飞飞, 李月明, 孔丽, 郝爱友, 有机化学, 2011, 31,1761.)
[13]	Zhang, W.; Waddell, P.M.; Tiedemann, M.A.; Padilla, C.E.; Mei, J.J.; Chen, L.Y.; Carrow, B.P. J. Am. Chem. Soc. 2018, 140,8841. pmid: 29944349
[14]	Chen, G.H.; Ma, X.S.; Guan, Z.B. J. Am. Chem. Soc. 2003, 125,6697.
[15]	Marks, T.J.; Chen, J.; Gao, Y. Angew. Chem., Int. Ed. 2020, 59,14726.
[16]	Zhu, Y.Q.; Li, S.H.; Liang, H.Q.; Xie, X.L.; Zhu, F.M. RSC Adv. 2019, 9,26582.
[17]	Hong, M.; Wang, Y.X.; Mu, H.L.; Li, Y.S. Organometallics 2011, 30,4678.
[18]	Chen, Z.; Li, J.F.; Tao, W.J.; Sun, X.L.; Yang, X.H.; Tang, Y. Macromolecules 2013, 46,2870.
[19]	(a) Chen, R.F.; Qian, C.T.; Li, Y.; Zou, F.L. Chin. J. Org. Chem. 2000, 20,712. (in Chinese)
	( 陈瑞芳, 钱长涛, 李杨, 邹丰楼, 有机化学, 2000, 20,712.)
	(b) Su, B.Y.; Jia, P.Y.; Wang, Y.Z.; Li, Y.N.; Huang, H.; Li, Q.D. Chin. J. Org. Chem. 2016, 36,2344. (in Chinese)
	( 苏碧云, 郏佩瑜, 王彦昭, 李亚宁, 黄鹤, 李谦定, 有机化学, 2016, 36,2344.)
[20]	(a) Nakamura, A.; Anselment, T.M. J.; Claverie, J.; Goodall, B.; Jordan, R.F.; Mecking, S.; Rieger, B.; Sen, A.; Van Leeuwen, P. W., N.M.; Nozaki, K. Acc. Chem. Res. 2013, 46,1438.
	(b) Chen, C.L. Nat. Rev. Chem. 2018, 2,6.
	(c) Mitchell, N.E.; Long, B.K. Polym. Int. 2019, 68,14.
	(d) Tan, C.; Chen, C.L. Angew. Chem., Int. Ed. 2019, 58,7192.
	(e) Wang, F.Z.; Chen, C.L. Polym. Chem. 2019, 10,2354.
[21]	Klabunde, U.; Itten, S.D. J. Mol. Catal. 1987, 41,123.
[22]	Johnson, L.K.; Mecking, S.; Brookhart, M. J. Am. Chem. Soc. 1996, 118,267.
[23]	Younkin, T.R.; Connor, E.F.; Henderson, J.I.; Friedrich, S.K.; Grubbs, R.H.; Bansleben, D.A. Science 2000, 287,460.
[24]	Carrow, B.P.; Nozaki, K. J. Am. Chem. Soc. 2012, 134,8802.
[25]	Drent, E.; Van Dijk, R.; Van Ginkel, R.; Van Oort, B.; Pugh, R.I. Chem. Commun. 2002,744.
[26]	Friedberger, T.; Wucher, P.; Mecking, S. J. Am. Chem. Soc. 2012, 134,1010.
[27]	Zhao, Y.; Gao, H.Y.; Zhang, L.; Wu, Q. Chin. Polym. Bull. 2009,27. (in Chinese)
	( 赵烨, 高海洋, 张玲, 伍青, 高分子通报, 2009,27.)
[28]	Chen, M.; Chen, C.L. Acta Polym. Sin. 2018,1372. (in Chinese)
	( 陈敏, 陈昶乐, 高分子学报, 2018,1372.)
[29]	Jian, Z.B. Acta Polym. Sin. 2018,1359. (in Chinese)
	( 简忠保, 高分子学报, 2018,1359.)
[30]	Cui, D.M. Acta Polym. Sin. 2020,1. (in Chinese)
	( 崔冬梅, 高分子学报, 2020,1.)
[31]	Mu, H.; Pan, L.; Song, D.; Li, Y. Chem. Rev. 2015, 115,12091.
[32]	Yuan, S.-F.; Yan, Y.; Solan, G.A.; Ma, Y.; Sun, W.-H. Coord. Chem. Rev. 2020, 411,213254.
[33]	Dai, S.; Li, S. Polymer 2020, 200,122607.
[34]	Li, M.Y.; Cai, Z.G.; Eisen, M.S. Organometallics 2018, 37,4753.
[35]	Chen, Z.; Brookhart, M. Acc. Chem. Res. 2018, 51,1831. pmid: 30028122
[36]	(a) Chen, M.; Yang, B.P.; Chen, C.L. Synlett 2016, 27,1297.
	(b) Chen, C.L. ACS Catal. 2018, 8,5506.
	(c) Kaiser, J.M.; Long, B.K. Coord. Chem. Rev. 2018, 372,141.
[37]	(a) Guo, L.H.; Dai, S.Y.; Sui, X.L.; Chen, C.L. ACS Catal. 2016, 6,428.
	(b) Flisak, Z.; Sun, W.-H. ACS Catal. 2015, 5,4713.
[38]	Nakamura, A.; Ito, S.; Nozaki, K. Chem. Rev. 2009, 109,5215.
[39]	Camacho, D.H.; Guan, Z. Chem. Commun. 2010, 46,7879.
[40]	(a) Zhang, Y.P.; Mu, H.L.; Pan, L.; Wang, X.L.; Li, Y.S. ACS Catal. 2018, 8,5963.
	(b) Nomura, K. J. Synth. Org. Chem. Jpn. 2010, 68,1150.
	(c) Gaikwad, S.R.; Deshmukh, S.S.; Koshti, V.S.; Poddar, S.; Gonnade, R.G.; Rajamohanan, P.R.; Chikkali, S.H. Macromolecules 2017, 50,5748.
[41]	(a) Radlauer, M.R.; Day, M.W.; Agapie, T. J. Am. Chem. Soc. 2012, 134,1478.
	(b) Runzi, T.; Frohlich, D.; Mecking, S. J. Am. Chem. Soc. 2010, 132,17690.
	(c) Keyes, A.; Alhan, H.E. B.; Ordonez, E.; Ha, U.; Beezer, D.B.; Dau, H.; Liu, Y.-S.; Tsogtgerel, E.; Jones, G.R.; Harth, E. Angew. Chem., Int. Ed. 2019, 58,12370.
[42]	Schuster, N.; Runzi, T.; Mecking, S. Macromolecules 2016, 49,1172.
[43]	Huo, P.; Liu, W.Y.; He, X.H.; Wang, H.M.; Chen, Y.W. Organometallics 2013, 32,2291.
[44]	Mecking, S.; Johnson, L.K.; Wang, L.; Brookhart, M. J. Am. Chem. Soc. 1998, 120,888.
[45]	Park, S.; Takeuchi, D.; Osakada, K. J. Am. Chem. Soc. 2006, 128,3510.
[46]	Luo, S.; Jordan, R.F. J. Am. Chem. Soc. 2006, 128,12072.
[47]	(a) Guo, L.H.; Zou, C.; Dai, S.Y.; Chen, C.L. Polymers 2017, 9,122.
	(b) Li, M.; Wang, X.B.; Luo, Y.; Chen, C.L. Angew. Chem., Int. Ed. 2017, 56,11604.
[48]	(a) Popeney, C.S.; Camacho, D.H.; Guan, Z.B. J. Am. Chem. Soc. 2007, 129,10062.
	(b) Liu, F.-S.; Hu, H.-B.; Xu, Y.; Guo, L.-H.; Zai, S.-B.; Song, K.-M.; Gao, H.-Y.; Zhang, L.; Zhu, F.-M.; Wu, Q. Macromolecules 2009, 42,7789.
	(c) Guo, L.H.; Gao, H.Y.; Guan, Q.R.; Hu, H.B.; Deng, J.A.; Liu, J.; Liu, F.S.; Wu, Q. Organometallics 2012, 31,6054.
[49]	Avar, S.; Mortazavi, S.M. M.; Ahmadjo, S.; Zohuri, G.H. Appl. Organomet. Chem. 2018, 32,e4238.
[50]	Takeuchi, D.; Yamada, T.; Nakamaru, Y.; Osakada, K.; Aratani, I.; Suzuki, Y. Organometallics 2019, 38,2323.
[51]	Rosar, V.; Meduri, A.; Montini, T.; Fini, F.; Carfagna, C.; Fornasiero, P.; Balducci, G.; Zangrando, E.; Milani, B. ChemCatChem 2014, 6,2403.
[52]	(a) Allen, K.E.; Campos, J.; Daugulis, O.; Brookhart, M. ACS Catal. 2015, 5,456. pmid: 27960299
	(b) Chen, Z.; Liu, W.J.; Daugulis, O.; Brookhart, M. J. Am. Chem. Soc. 2016, 138,16120. pmid: 27960299
[53]	Chen, Z.; Leatherman, M.D.; Daugulis, O.; Brookhart, M. J. Am. Chem. Soc. 2017, 139,16013. pmid: 29083899
[54]	Matos, I.; Fernandes, S.N.; Liu, H.R.; Tevtia, A.K.; Singh, R.P.; Manda, L.; Lemos, F.; Marques, M.M. J. Appl. Polym. Sci. 2013, 129,1820.
[55]	Meduri, A.; Montini, T.; Ragaini, F.; Fornasiero, P.; Zangrando, E.; Milani, B. ChemCatChem 2013, 5,1170.
[56]	Rosar, V.; Meduri, A.; Montini, T.; Fornasiero, P.; Zangrando, E.; Milani, B. Dalton Trans. 2018, 47,2778.
[57]	Pan, H.J.; Zhu, L.; Li, J.W.; Zang, D.D.; Fu, Z.S.; Fan, Z.Q. J. Mol. Catal. A: Chem.2014, 390,76.
[58]	Popeney, C.S.; Guan, Z.B. J. Am. Chem. Soc. 2009, 131,12384.
[59]	Rhinehart, J.L.; Brown, L.A.; Long, B.K. J. Am. Chem. Soc. 2013, 135,16316. pmid: 24164257
[60]	Dai, S.Y.; Sui, X.L.; Chen, C.L. Angew. Chem., Int. Ed. 2015, 54,9948.
[61]	Dai, S.Y.; Chen, C.L. Angew. Chem., Int. Ed. 2016, 55,13281.
[62]	Dai, S.Y.; Chen, C.L. Macromolecules 2018, 51,6818.
[63]	Gong, Y.; Li, S.; Gong, Q.; Zhang, S.; Liu, B.; Dai, S. Organometallics 2019, 38,2919.
[64]	Muhammad, Q.; Tan, C.; Chen, C. Sci. Bull. 2020, 65,300.
[65]	Na, Y.N.; Dai, S.Y.; Chen, C.L. Macromolecules 2018, 51,4040.
[66]	Sui, X.L.; Hong, C.W.; Pang, W.M.; Chen, C.L. Mat. Chem. Front. 2017, 1,967.
[67]	Na, Y.N.; Zhang, D.; Chen, C.L. Polym. Chem. 2017, 8,2405.
[68]	Fang, J.; Sui, X.L.; Li, Y.G.; Chen, C.L. Polym. Chem. 2018, 9,4143.
[69]	Guo, L.H.; Liu, Y.L.; Sun, W.T.; Du, Q.; Yang, Y.L.; Kong, W.Y.; Liu, Z.; Chen, D.R. J. Organomet. Chem. 2018, 877,12.
[70]	Liao, Y.; Zhang, Y.; Cui, L.; Mu, H.; Jian, Z. Organometallics 2019, 38,2075.
[71]	Kanai, Y.; Foro, S.; Plenio, H. Organometallics 2019, 38,544.
[72]	Hu, X.; Zhang, Y.; Zhang, Y.; Jian, Z. ChemCatChem 2020, 12,2497.
[73]	Wang, R.K.; Zhao, M.H.; Chen, C.L. Polym. Chem. 2016, 7,3933.
[74]	Zhai, F.; Solomon, J.B.; Jordan, R.F. Organometallics 2017, 36,1873.
[75]	Zou, W.P.; Chen, C.L. Organometallics 2016, 35,1794.
[76]	Dall'anese, A.; Rosar, V.; Cusin, L.; Montini, T.; Balducci, G.; D'auria, I.; Pellecchia, C.; Fornasiero, P.; Felluga, F.; Milani, B. Organometallics 2019, 38,3498.
[77]	Zhong, S.H.; Tan, Y.X.; Zhong, L.; Gao, J.; Liao, H.; Jiang, L.; Gao, H.Y.; Wu, Q. Macromolecules 2017, 50,5661.
[78]	Du, C.; Zhong, L.; Gao, J.; Zhong, S.H.; Liao, H.; Gao, H.Y.; Wu, Q. Polym. Chem. 2019, 10,2029.
[79]	Zhong, L.; Li, G.L.; Liang, G.D.; Gao, H.Y.; Wu, Q. Macromolecules 2017, 50,2675.
[80]	Huo, P.; Li, J.; Liu, W.; Mei, G.; He, X. RSC Adv. 2017, 7,51858.
[81]	He, X.; Deng, Y.; Jiang, X.; Wang, Z.; Yang, Y.; Han, Z.; Chen, D. Polym. Chem. 2017, 8,2390.
[82]	Huo, P.; Liu, W.Y.; He, X.H.; Wei, Z.H.; Chen, Y.W. Polym. Chem. 2014, 5,1210.
[83]	Tian, J.; He, X.; Liu, J.; Deng, X.; Chen, D. RSC Adv. 2016, 6,22908.
[84]	Long, B.K.; Eagan, J.M.; Mulzer, M.; Coates, G.W. Angew. Chem., Int. Ed. 2016, 55,7106.
[85]	Hu, H.; Chen, D.; Gao, H.; Zhong, L.; Wu, Q. Polym. Chem. 2016, 7,529.
[86]	Zheng, T.; Liao, H.; Gao, J.; Zhong, L.; Gao, H.Y.; Wu, Q. Polym. Chem. 2018, 9,3088.
[87]	Kawakami, T.; Ito, S.; Nozaki, K. Dalton Trans. 2015, 44,20745. doi: 10.1039/C5DT03551A
[88]	Zhu, L.; Fu, Z.S.; Pan, H.J.; Feng, W.; Chen, C.L.; Fan, Z.Q. Dalton Trans. 2014, 43,2900. pmid: 24343297
[89]	Na, Y.N.; Wang, X.B.; Lian, K.B.; Yun, Z.; Li, W.M.; Yi, L.; Chen, C.L. ChemCatChem 2017, 9,1062.
[90]	Huo, P.; Liu, W.Y.; He, X.H.; Chen, Y.W. J. Polym. Sci., Part A: Polym. Chem. 2014, 52,3213.
[91]	Tafazolian, H.; Culver, D.B.; Conley, M.P. Organometallics 2017, 36,2385.
[92]	Culver, D.B.; Tafazolian, H.; Conley, M.P. Organometallics 2018, 37,1001.
[93]	Radlauer, M.R.; Buckley, A.K.; Henling, L.M.; Agapie, T. J. Am. Chem. Soc. 2013, 135,3784. pmid: 23425209
[94]	Cheng, H.L.; Wang, H.J.; Li, Y.Q.; Hu, Y.M.; Zhang, X.Q.; Cai, Z.G. J. Catal. 2018, 368,291.
[95]	Takeuchi, D.; Chiba, Y.; Takano, S.; Osakada, K. Angew. Chem., Int. Ed. 2013, 52,12536.
[96]	Chen, Z.T.; Yao, E.D.; Wang, J.C.; Gong, X.Y.; Ma, Y.G. Macromolecules 2016, 49,8848. doi: 10.1021/acs.macromol.6b02078
[97]	Chen, Y.; Mandal, S.; Sen, A. Organometallics 2010, 29,3160.
[98]	He, F.; Chen, Y.; He, X.; Chen, M.; Zhou, W.; Wu, Q. J. Polym. Sci., Part A: Polym. Chem. 2009, 47,3990.
[99]	Huang, R.; He, X.H.; Chen, Y.W.; Nie, H.R.; Zhou, W.H. Polym. Adv. Technol. 2012, 23,483.
[100]	Xing, Y.; Chen, Y.; He, X. J. Polym. Sci., Part A: Polym. Chem. 2011, 49,4425.
[101]	Tian, J.W.; Zhu, H.Y.; Liu, J.Y.; Chen, D.F.; He, X.H. Appl. Organomet. Chem. 2014, 28,702.
[102]	Xing, Y.P.; He, X.H.; Chen, Y.W.; Nie, H.R.; Wu, Q. Polym. Bull. 2011, 66,1149.
[103]	Zhou, W.; He, X.; Chen, Y.; Chen, M.; Shi, L.; Wu, Q. J. Appl. Polym. Sci. 2011, 120,2008.
[104]	Wang, K.; Chen, Y.; He, X.; Liu, Y.; Zhou, W. J. Polym. Sci., Part A: Polym. Chem. 2011, 49,3304.
[105]	He, X.; Liu, Y.; Chen, L.; Chen, Y.; Chen, D. J. Polym. Sci., Part A: Polym. Chem. 2012, 50,4695.
[106]	Wang, X.F.; He, X.H.; Chen, D.F.; Chen, Y.W. J. Polym. Eng. 2012, 32,415.
[107]	Chen, L.; Zhong, Z.C.; Chen, C.; He, X.H.; Chen, Y.W. J. Organomet. Chem. 2014, 752,100.
[108]	He, X.H.; Liu, J.Y.; Chen, L.; Zhu, H.Y.; Wang, J. Chem. J. Chin. Univ. 2015, 36,575. (in Chinese)
	( 贺晓慧, 刘菁胤, 陈璐, 朱宏宇, 王娟, 高等学校化学学报, 2015, 36,575.)
[109]	He, X.H.; Yang, Y.P.; Wang, S.L.; Han, Z.L.; Tu, G.S.; Zhang, F.; Huang, S.M.; Wang, Z.J.; Chen, D.F. RSC Adv. 2017, 7,48745.
[110]	Tian, J.W.; He, X.H.; Liu, J.Y.; Deng, X.D.; Chen, D.F. RSC Adv. 2015, 5,61851.
[111]	Fu, X.; Zhang, L.J.; Tanaka, R.; Shiono, T.; Cai, Z.G. Macromolecules 2017, 50,9216.
[112]	Ding, L.; Cheng, H.L.; Li, Y.Q.; Tanaka, R.; Shiono, T.; Cai, Z.G. Polym. Chem. 2018, 9,5476.
[113]	Cheng, H.L.; Su, Y.; Hu, Y.M.; Zhang, X.Q.; Cai, Z.G. Polymers 2018, 10,10.
[114]	Zou, C.; Dai, S.Y.; Chen, C.L. Macromolecules 2018, 51,49.
[115]	(a) Mu, H.L.; Li, Y.G.; Li, Y.S. Chin. J. Appl. Chem. 2012, 29,1381. (in Chinese)
	( 穆红亮, 李彦国, 李悦生, 应用化学, 2012, 29,1381.)
	(b) Gibson, V.C.; Tomov, A. Chem. Commun. 2001,1964.
[116]	Guo, C.-Y.; Peulecke, N.; Basvani, K.R.; Kinderman, M.K.; Heinicke, J. Macromolecules 2010, 43,1416.
[117]	Konishi, Y.; Tao, W.J.; Yasuda, H.; Ito, S.; Oishi, Y.; Ohtaki, H.; Tanna, A.; Tayano, T.; Nozaki, K. ACS Macro Lett. 2018, 7,213.
[118]	Xin, B.S.; Sato, N.; Tanna, A.; Oishi, Y.; Konishi, Y.; Shimizu, F. J. Am. Chem. Soc. 2017, 139,3611. pmid: 28218852
[119]	Zhang, Y.P.; Mu, H.L.; Wang, X.L.; Pan, L.; Li, Y.S. ChemCatChem 2019, 11,2329.
[120]	Zhang, Y.-P.; Li, W.-W.; Li, B.-X.; Mu, H.-L.; Li, Y.-S. Dalton Trans. 2015, 44,7382.
[121]	Zhang, Y.P.; Mu, H.L.; Li, Y.G.; Li, Y.S. Appl. Organomet. Chem. 2018, 32,9.
[122]	Zhang, Y.; Zhang, Y.; Chi, Y.; Jian, Z. Dalton Trans. 2020, 49,2636.
[123]	Zhang, Y.; Jian, Z. Polymer 2020, 194,122410.
[124]	Skupov, K.M.; Marella, P.R.; Simard, M.; Yap, G.P. A.; Allen, N.; Conner, D.; Goodall, B.L.; Claverie, J.P. Macromol. Rapid Commun. 2007, 28,2033.
[125]	Luo, S.; Vela, J.; Lief, G.R.; Jordan, R.F. J. Am. Chem. Soc. 2007, 129,8946.
[126]	Ito, S.; Munakata, K.; Nakamura, A.; Nozaki, K. J. Am. Chem. Soc. 2009, 131,14606. pmid: 19785406
[127]	Kochi, T.; Noda, S.; Yoshimura, K.; Nozaki, K. J. Am. Chem. Soc. 2007, 129,8948. pmid: 17595086
[128]	Weng, W.; Shen, Z.; Jordan, R.F. J. Am. Chem. Soc. 2007, 129,15450. doi: 10.1021/ja0774717 pmid: 18027953
[129]	Neuwald, B.; Oelscher, F.; Goettker-Schnetmann, I.; Mecking, S. Organometallics 2012, 31,3128.
[130]	Jian, Z.B.; Wucher, P.; Mecking, S. Organometallics 2014, 33,2879.
[131]	Piche, L.; Daigle, J.-C.; Rehse, G.; Claverie, J.P. Chem.-Eur. J. 2012, 18,3277. pmid: 22331790
[132]	Kryuchkov, V.A.; Daigle, J.-C.; Skupov, K.M.; Claverie, J.P.; Winnik, F.M. J. Am. Chem. Soc. 2010, 132,15573. pmid: 20945896
[133]	Daigle, J.-C.; Piche, L.; Claverie, J.P. Macromolecules 2011, 44,1760.
[134]	Neuwald, B.; Falivene, L.; Caporaso, L.; Cavallo, L.; Mecking, S. Chem.-Eur. J. 2013, 19,17773.
[135]	Wucher, P.; Goldbach, V.; Mecking, S. Organometallics 2013, 32,4516.
[136]	Guironnet, D.; Roesle, P.; Rünzi, T.; Göttker-Schnetmann, I.; Mecking, S. J. Am. Chem. Soc. 2009, 131,422.
[137]	Zhang, D.; Chen, C.L. Angew. Chem., Int. Ed. 2017, 56,14672.
[138]	Daigle, J.-C.; Piche, L.; Arnold, A.; Claverie, J.P. ACS Macro Lett. 2012, 1,343.
[139]	Jian, Z.; Baier, M.C.; Mecking, S. J. Am. Chem. Soc. 2015, 137,2836. pmid: 25675331
[140]	Jian, Z.; Mecking, S. Angew. Chem., Int. Ed. 2015, 54,15845.
[141]	Jian, Z.; Mecking, S. Macromolecules 2016, 49,4395.
[142]	Gaikwad, S.R.; Deshmukh, S.J. S.; Gonnade, R.G.; Rajamohanan, P.R.; Chikkali, S.H. ACS Macro Lett. 2015, 4,933.
[143]	Yasuda, H.; Nakano, R.; Ito, S.; Nozaki, K. J. Am. Chem. Soc. 2018, 140,1876. doi: 10.1021/jacs.7b12593 pmid: 29307177
[144]	Ölscher, F.; Göttker-Schnetmann, I.; Monteil, V.; Mecking, S. J. Am. Chem. Soc. 2015, 137,14819.
[145]	(a) Li, S.; Liu, D.; Wang, Z.; Cui, D. ACS Catal. 2018, 8,6086.
	(b) Liu, B.; Qiao, K.; Fang, J.; Wang, T.; Wang, Z.; Liu, D.; Xie, Z.; Maron, L.; Cui, D. Angew. Chem., Int. Ed. 2018, 57,14896.
	(c) Wang, T.T.; Liu, D.T.; Cui, D.M. Macromolecules 2019, 52,9555.
[146]	Borkar, S.; Newsham, D.K.; Sen, A. Organometallics 2008, 27,3331.
[147]	Cui, L.; Chen, M.; Chen, C.L.; Liu, D.T.; Jian, Z.B. Macromolecules 2019, 52,7197.
[148]	Shen, Z.; Jordan, R.F. Macromolecules 2010, 43,8706.
[149]	Lanzinger, D.; Giuman, M.M.; Anselment, T.M. J.; Rieger, B. ACS Macro Lett. 2014, 3,931.
[150]	Bouilhac, C.; Rünzi, T.; Mecking, S. Macromolecules 2010, 43,3589.
[151]	Ravasio, A.; Boggioni, L.; Tritto, I. Macromolecules 2011, 44,4180.
[152]	Jian, Z.B.; Leicht, H.; Mecking, S. Macromol. Rapid Commun. 2016, 37,934.
[153]	Chen, M.; Chen, C.L. Angew. Chem., Int. Ed. 2020, 59,1206.
[154]	Jian, Z.B.; Mecking, S. Macromolecules 2016, 49,4057.
[155]	Liang, T.; Chen, C.L. Organometallics 2017, 36,2338.
[156]	Yang, B.P.; Xiong, S.Y.; Chen, C.L. Polym. Chem. 2017, 8,6272.
[157]	Tan, C.; Qasim, M.; Pang, W.; Chen, C. Polym. Chem. 2020, 11,411.
[158]	Anselment, T.M. J.; Anderson, C.E.; Rieger, B.; Boeddinghaus, M.B.; Fassler, T.F. Dalton Trans. 2011, 40,8304. pmid: 21677979
[159]	Leicht, H.; Göttker-Schnetmann, I.; Mecking, S. Angew. Chem., Int. Ed. 2013, 52,3963.
[160]	Wucher, P.; Schwaderer, J.B.; Mecking, S. ACS Catal. 2014, 4,2672.
[161]	Ito, S.; Kanazawa, M.; Munakata, K.; Kuroda, J.-I.; Okumura, Y.; Nozaki, K. J. Am. Chem. Soc. 2011, 133,1232. doi: 10.1021/ja1092216 pmid: 21204540
[162]	Ota, Y.; Ito, S.; Kuroda, J.-I.; Okumura, Y.; Nozaki, K. J. Am. Chem. Soc. 2014, 136,11898. pmid: 25116272
[163]	Ota, Y.; Ito, S.; Kobayashi, M.; Kitade, S.; Sakata, K.; Tayano, T.; Nozaki, K. Angew. Chem., Int. Ed. 2016, 55,7505.
[164]	Xia, J.; Zhang, Y.X.; Hu, X.Q.; Ma, X.; Cui, L.; Zhang, J.F.; Jian, Z.B. Polym. Chem. 2019, 10,546.
[165]	Wu, Z.X.; Chen, M.; Chen, C.L. Organometallics 2016, 35,1472.
[166]	Wu, Z.X.; Hong, C.W.; Du, H.X.; Pang, W.M.; Chen, C.L. Polymers 2017, 9,168.
[167]	Zou, C.; Pang, W.M.; Chen, C.L. Sci. China: Chem. 2018, 61, 1175.
[168]	Black, R.E.; Jordan, R.F. Organometallics 2017, 36,3415.
[169]	Wada, S.; Jordan, R.F. Angew. Chem., Int. Ed. 2017, 56,1820.
[170]	Ito, S.; Ota, Y.; Nozaki, K. Dalton Trans. 2012, 41,13807. doi: 10.1039/c2dt31771k pmid: 23059906
[171]	Chen, M.; Chen, C. ACS Catal. 2017, 7,1308.
[172]	Song, G.Z.; Pang, W.M.; Li, W.M.; Chen, M.; Chen, C.L. Polym. Chem. 2017, 8,7400.
[173]	Liang, T.; Chen, C.L. Inorg. Chem. 2018, 57,14913. doi: 10.1021/acs.inorgchem.8b02687 pmid: 30411610
[174]	Xia, J.; Zhang, Y.X.; Zhang, J.F.; Jian, Z.B. Organometallics 2019, 38,1118.
[175]	Nakano, R.; Nozaki, K. J. Am. Chem. Soc. 2015, 137,10934. doi: 10.1021/jacs.5b06948 pmid: 26259109
[176]	Tao, W.J.; Nakano, R.; Ito, S.; Nozaki, K. Angew. Chem., Int. Ed. 2016, 55,2835.
[177]	Tao, W.; Akita, S.; Nakano, R.; Ito, S.; Hoshimoto, Y.; Ogoshi, S.; Nozaki, K. Chem. Commun. 2017, 53,2630.
[178]	Tao, W.; Wang, X.; Ito, S.; Nozaki, K. J. Polym. Sci., Part A: Polym. Chem. 2019, 57,474.
[179]	Carrow, B.P.; Nozaki, K. Macromolecules 2014, 47,2541.
[180]	Mitsushige, Y.; Carrow, B.P.; Ito, S.; Nozaki, K. Chem. Sci. 2016, 7,737. pmid: 29896357
[181]	Cai, Z.Z.; Do, L.H. Organometallics 2018, 37,3874.
[182]	Contrella, N.D.; Sampson, J.R.; Jordan, R.F. Organometallics 2014, 33,3546.
[183]	Sui, X.L.; Dai, S.Y.; Chen, C.L. ACS Catal. 2015, 5,5932.
[184]	Hong, C.W.; Sui, X.L.; Li, Z.Q.; Pang, W.M.; Chen, M. Dalton Trans. 2018, 47,8264. doi: 10.1039/c8dt01018h pmid: 29888779
[185]	Ye, J.H.; Mu, H.L.; Wang, Z.; Jian, Z.B. Organometallics 2019, 38,2990.
[186]	Mu, H.-L.; Ye, J.-H.; Zhou, G.-L.; Li, K.-K.; Jian, Z.-B. Chin. J. Polym. Sci. 2019, 38,579.
[187]	Zhou, G.; Mu, H.; Jian, Z. J. Catal. 2020, 383,215.
[188]	Li, K.; Ye, J.; Wang, Z.; Mu, H.; Jian, Z. Polym. Chem. 2020, 11,2740.
[189]	Mitsushige, Y.; Yasuda, H.; Carrow, B.P.; Ito, S.; Kobayashi, M.; Tayano, T.; Watanabe, Y.; Okuno, Y.; Hayashi, S.; Kuroda, J.; Okumura, Y.; Nozaki, K. ACS Macro Lett. 2018, 7,305.
[190]	Jung, J.; Yasuda, H.; Nozaki, K. Macromolecules 2020, 53,2547.
[191]	Chen, M.; Chen, C.L. Angew. Chem., Int. Ed. 2018, 57,3094.
[192]	Sun, J.J.; Chen, M.; Luo, G.; Chen, C.L.; Luo, Y. Organometallics 2019, 38,638.
[193]	Si, G.F.; Na, Y.N.; Chen, C.L. ChemCatChem 2018, 10,5135.
[194]	Gao, J.X.; Yang, B.P.; Chen, C.L. J. Catal. 2019, 369,233.
[195]	Zou, C.; Tan, C.; Pang, W.M.; Chen, C.L. ChemCatChem 2019, 11,5339.
[196]	Brookhart, M.; Kunitsky, K.; Malinoski, J.; Wang, L, Wang, Y.; Liu, W.; Johnson, L.; Kreutzer, K.; Ittel, S. WO 2002059165, 2002.
[197]	Liang, T.; Goudari, S.B.; Chen, C. Nat. Commun. 2020, 11,372. pmid: 31953416
[198]	Franssen, N.M. G.; Reek, J.N. H.; De Bruin, B. Dalton Trans. 2013, 42,9058. doi: 10.1039/c3dt32941k pmid: 23361412
[199]	Walsh, D.J.; Hyatt, M.G.; Miller, S.A.; Guironnet, D. ACS Catal. 2019, 9,11153.
[200]	Dai, S.; Li, S.; Xu, G.; Chen, C. Macromolecules 2020, 53,2539.
[201]	Parisi, L.R.; Scheibel, D.; Lin, S.; Bennett, E.M.; Lodge, J.M.; Miri, M. Polymer 2017, 114,319.

后过渡金属配合物催化烯烃-极性单体共聚