后过渡金属配合物催化烯烃-极性单体共聚
收稿日期: 2020-09-03
修回日期: 2020-10-30
网络出版日期: 2020-11-19
基金资助
上海市聚烯烃合成技术及过程控制专业技术服务平台基金(19DZ2290900)
Late Transition Metal Complexes for Olefin Copolymerization with Polar Monomers
Received date: 2020-09-03
Revised date: 2020-10-30
Online published: 2020-11-19
Supported by
Shanghai Professional and Technical Service Platform of Polyolefin Synthesis and Process Control(19DZ2290900)
李永清 , 王凡 , 曹育才 . 后过渡金属配合物催化烯烃-极性单体共聚[J]. 有机化学, 2021 , 41(4) : 1396 -1433 . DOI: 10.6023/cjoc202009008
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
| [1] | (a) Hlatky, G.G. Coord. Chem. Rev. 2000, 199,235. |
| [1] | (b) Severn, J.R.; Chadwick, J.C.; Duchateau, R.; Friederichs, N. Chem. Rev. 2005, 105,4073. |
| [1] | (c) Hlatky, G.G. Chem. Rev. 2000, 100,1347. |
| [1] | (d) Chen, E.Y. X. Chem. Rev. 2009, 109,5157. |
| [2] | Coates, G.W. Chem. Rev. 2000, 100,1223. |
| [3] | Gibson, V.C.; Spitzmesser, S.K. Chem. Rev. 2003, 103,283. |
| [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. |
| [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) |
| [6] | ( 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.) |
| [6] | (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) |
| [6] | ( 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.) |
| [6] | (c) Li, B.G.; Zhang, M.X.; Liu, W.F.; Wang, W.J. Chem. Ind. Eng. Prog. 2017, 36,3135. (in Chinese) |
| [6] | ( 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. |
| [7] | (b) Na, Y.; Chen, C. Angew. Chem., Int. Ed. 2020, 59,7953. |
| [7] | (c) Gao, J.X.; Cai, W.; Hu, Y.; Chen, C.L. Polym. Chem. 2019, 10,1416. |
| [7] | (d) Takano, S.; Takeuchi, D.; Osakada, K.; Akamatsu, N.; Shishido, A. Angew. Chem., Int. Ed. 2014, 53,9246. |
| [7] | (e) Yao, H.L.; He, X.H.; Chen, L.; Chen, Y.W.; Chen, D.F. J. Appl. Polym. Sci. 2013, 128,3540. |
| [7] | (f) Rünzi, T.; Mecking, S. Adv. Funct. Mater. 2014, 24,387. |
| [8] | (a) Novák, I.; Borsig, E.; Hr?ková, L.U.; Fiedlerová, A.; Kleinová, A.; Pollák, V. Polym. Eng. Sci. 2007, 47,1207. |
| [8] | (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. |
| [9] | (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) |
| [10] | ( 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. |
| [12] | (b) Parkatzidis, K.; Wang, H.S.; Truong, N.P.; Anastasaki, A. Chem 2020, 6,1575. |
| [12] | (c) Tasdelen, M.A.; Kahveci, M.U.; Yagci, Y. Prog. Polym. Sci. 2011, 36,455. |
| [12] | (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) |
| [12] | ( 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. |
| [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) |
| [19] | ( 陈瑞芳, 钱长涛, 李杨, 邹丰楼, 有机化学, 2000, 20,712.) |
| [19] | (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) |
| [19] | ( 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. |
| [20] | (b) Chen, C.L. Nat. Rev. Chem. 2018, 2,6. |
| [20] | (c) Mitchell, N.E.; Long, B.K. Polym. Int. 2019, 68,14. |
| [20] | (d) Tan, C.; Chen, C.L. Angew. Chem., Int. Ed. 2019, 58,7192. |
| [20] | (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) |
| [27] | ( 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) |
| [28] | ( 陈敏, 陈昶乐, 高分子学报, 2018,1372.) |
| [29] | Jian, Z.B. Acta Polym. Sin. 2018,1359. (in Chinese) |
| [29] | ( 简忠保, 高分子学报, 2018,1359.) |
| [30] | Cui, D.M. Acta Polym. Sin. 2020,1. (in Chinese) |
| [30] | ( 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. |
| [36] | (a) Chen, M.; Yang, B.P.; Chen, C.L. Synlett 2016, 27,1297. |
| [36] | (b) Chen, C.L. ACS Catal. 2018, 8,5506. |
| [36] | (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. |
| [37] | (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. |
| [40] | (b) Nomura, K. J. Synth. Org. Chem. Jpn. 2010, 68,1150. |
| [40] | (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. |
| [41] | (b) Runzi, T.; Frohlich, D.; Mecking, S. J. Am. Chem. Soc. 2010, 132,17690. |
| [41] | (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. |
| [47] | (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. |
| [48] | (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. |
| [48] | (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. |
| [52] | (b) Chen, Z.; Liu, W.J.; Daugulis, O.; Brookhart, M. J. Am. Chem. Soc. 2016, 138,16120. |
| [53] | Chen, Z.; Leatherman, M.D.; Daugulis, O.; Brookhart, M. J. Am. Chem. Soc. 2017, 139,16013. |
| [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. |
| [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. |
| [88] | Zhu, L.; Fu, Z.S.; Pan, H.J.; Feng, W.; Chen, C.L.; Fan, Z.Q. Dalton Trans. 2014, 43,2900. |
| [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. |
| [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. |
| [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) |
| [108] | ( 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) |
| [115] | ( 穆红亮, 李彦国, 李悦生, 应用化学, 2012, 29,1381.) |
| [115] | (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. |
| [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. |
| [127] | Kochi, T.; Noda, S.; Yoshimura, K.; Nozaki, K. J. Am. Chem. Soc. 2007, 129,8948. |
| [128] | Weng, W.; Shen, Z.; Jordan, R.F. J. Am. Chem. Soc. 2007, 129,15450. |
| [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. |
| [132] | Kryuchkov, V.A.; Daigle, J.-C.; Skupov, K.M.; Claverie, J.P.; Winnik, F.M. J. Am. Chem. Soc. 2010, 132,15573. |
| [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.; G?ttker-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. |
| [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. |
| [144] | ?lscher, F.; G?ttker-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. |
| [145] | (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. |
| [145] | (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. |
| [159] | Leicht, H.; G?ttker-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. |
| [162] | Ota, Y.; Ito, S.; Kuroda, J.-I.; Okumura, Y.; Nozaki, K. J. Am. Chem. Soc. 2014, 136,11898. |
| [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. |
| [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. |
| [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. |
| [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. |
| [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. |
| [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. |
| [198] | Franssen, N.M. G.; Reek, J.N. H.; De Bruin, B. Dalton Trans. 2013, 42,9058. |
| [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. |
/
| 〈 |
|
〉 |
