Enantiomer-selective Living Polymerization of rac-Phenyl Isocyanide Using Chiral Palladium Catalyst
- Corresponding author: Na Liu, liuna@hfut.edu.cn
Citation:
Jian Huang, Ling Shen, Hui Zou, Na Liu. Enantiomer-selective Living Polymerization of rac-Phenyl Isocyanide Using Chiral Palladium Catalyst[J]. Chinese Journal of Polymer Science,
;2018, 36(7): 799-804.
doi:
10.1007/s10118-018-2136-5
Okamoto, Y.; Suzuki, K.; Ohta, K.; Hatada, K.; Yuki, H. Optically active poly(triphenylmethyl methacrylate) with one-handed helical conformation. J. Am. Chem. Soc. 1979, 101(16), 4763-4765.
doi: 10.1021/ja00510a072
Miyake, G. M.; Mariott, W. R.; Chen, E. Y. X. Asymmetric coordination polymerization of acrylamides by enantiomeric metallocenium ester enolate catalysts. J. Am. Chem. Soc. 2007, 129(21), 6724-6725.
doi: 10.1021/ja072073p
Wang, R.; Li, X. F.; Bai, J. W.; Zhang, J.; Liu, A. H.; Wan, X. H. Chiroptical and thermotropic properties of helical styrenic polymers: effect of achiral group. Macromolecules 2014, 47(5), 1553-1562.
doi: 10.1021/ma500147z
Cui, J. X.; Zhang, J.; Wan, X. H. Unexpected stereomutation dependence on the chemical structure of helical vinyl glycopolymers. Chem. Commun. 2012, 48(36), 4341-4343.
doi: 10.1039/c2cc00036a
Zhu, Y. Y.; Yin, T. T.; Li, X. L.; Su, M.; Xue, Y. X.; Yu, Z. P.; Liu, N.; Yin, J.; Wu, Z. Q. Synthesis and chiroptical properties of helical polyallenes bearing chiral amide pendants. Macromolecules 2014, 47(20), 7021-7029.
doi: 10.1021/ma5019022
Wu, Z. Q.; Radcliffe, J. D.; Ono, R. J.; Chen, Z.; Li, Z. C.; Bielawski, C. W. Synthesis of conjugated diblock copolymers: two mechanistically distinct, sequential living polymerizations using a single catalyst. Polym. Chem. 2012, 3(4), 874-881.
doi: 10.1039/c2py00566b
Zhang, W. M.; Zhang, J.; Qiao, Z.; Yin, J. Functionally oriented tumor microenvironment responsive polymeric nanoassembly: engineering and applications. Chinese J. Polym. Sci. 2018, 36(3), 273-287.
doi: 10.1007/s10118-018-2035-9
Makiguchi, W.; Kobayashi, S.; Furusho, Y.; Yashima, E. Formation of a homo double helix of a conjugated polymer with carboxy groups and amplification of the macromolecular helicity by chiral amines sandwiched between the strands. Angew. Chem. Int. Ed. 2013, 52(20), 5275-5279.
doi: 10.1002/anie.201301005
Zhou, L.; Jiang, Z. Q.; Xu, N.; Liu, N.; Wu, Z. Q. Polythiophene-block-poly(phenyl isocyanide) copolymers: one-pot synthesis, properties and applications. Chinese J. Polym. Sci. 2017, 35(12), 1447-1456.
doi: 10.1007/s10118-017-2003-9
Zhou, L.; Shen, L.; Huang, J.; Liu, N.; Zhu, Y. Y.; Wu, Z. Q. Optically active helical polyisocyanides bearing chiral phosphine pendants: facile synthesis and application in enantioselective Rauhut-currier reaction. Chinese J. Polym. Sci. 2018, 36(2), 163-170.
doi: 10.1007/s10118-018-2044-8
Green, M. M.; Peterson, N. C.; Sato, T.; Teramoto, A.; Cook, R.; Lifson, S. A helical polymer with a cooperative response to chiral information. Science 1995, 268(5219), 1860-1866.
doi: 10.1126/science.268.5219.1860
Li, J.; Schuster, G. B.; Cheon, K. S.; Green, M. M.; Selinger, J. V. Switching a helical polymer between mirror images using circularly polarized light. J. Am. Chem. Soc. 2000, 122(11), 2603-2612.
doi: 10.1021/ja993290w
Maeda, K.; Wakasone, S.; Shimomura, K.; Ikai, T.; Kanoh, S. Helical polymer brushes with a preferred-handed helix-sense triggered by a terminal optically active group in the pendant. Chem. Commun. 2012, 48(27), 3342-3344.
doi: 10.1039/c2cc00024e
Sakai, N.; Satoh, T.; Kakuchi, T. Rod-like amphiphile of diblock polyisocyanate leading to cylindrical micelle and spherical vesicle in water. Macromolecules 2014, 47(5), 1699-1704.
doi: 10.1021/ma500097t
Reuther, J. F.; DeSousa, J. D.; Novak, B. M. Direct probing of regioregularity for polycarbodiimide systems via 15N NMR analysis. Macromolecules 2012, 45(19), 7719-7728.
doi: 10.1021/ma301448b
Reuther, J. F.; Novak, B. M. Evidence of entropy-driven bistability through 15N NMR analysis of a temperature- and solvent-induced, chiroptical switching polycarbodiimide. J. Am. Chem. Soc. 2013, 135(51), 19292-19303.
doi: 10.1021/ja4098803
Budhathoki-Uprety, J.; Jena, P. V.; Roxbury, D.; Heller, D. A. Helical polycarbodiimide cloaking of carbon nanotubes enables inter-nanotube exciton energy transfer modulation. J. Am. Chem. Soc. 2014, 136(44), 15545-15550.
doi: 10.1021/ja505529n
Reuther, J. F.; Siriwardane, D. A.; Kulikov, O. V.; Batchelor, B. L.; Campos, R.; Novak, B. M. Facile synthesis of rod-coil block copolymers with chiral, helical polycarbodiimide segments via postpolymerization CuAAC " click” coupling of functional end groups. Macromolecules 2015, 48(10), 3207-3216.
doi: 10.1021/acs.macromol.5b00453
Liu, X.; Song, C.; Luo, X. F.; Yang, W. T.; Deng, J. P. " Sergeants and soldiers rule” in helical substitutedacetylene copolymer emulsions. Chinese J. Polym. Sci. 2013, 31(1), 179-186.
doi: 10.1007/s10118-013-1189-8
Akagi, K. Helical polyacetylene: asymmetric polymerization in a chiral liquid-crystal field. Chem. Rev. 2009, 109(11), 5354-5401.
doi: 10.1021/cr900198k
Matsushita, S.; Kyotani, M.; Akagi, K. Hierarchically controlled helical graphite films prepared from iodine-doped helical polyacetylene films using morphology-retaining carbonization. J. Am. Chem. Soc. 2011, 133(44), 17977-17992.
doi: 10.1021/ja2082922
Sakai, R.; Sakai, N.; Satoh, T.; Li, W.; Zhang, A. F.; Kakuchi, T. Strict size specificity in colorimetric anion detection based on poly(phenylacetylene) receptor bearing second generation lysine dendrons. Macromolecules 2011, 44(11), 4249-4257.
doi: 10.1021/ma200710r
Li, S.; Liu, K.; Kuang, G. C.; Masuda, T.; Zhang, A. F. Thermoresponsive helical poly(phenylacetylene)s. Macromolecules 2014, 47(10), 3288-3296.
doi: 10.1021/ma5003529
Song, C.; Liu, X.; Liu, D.; Ren, C. L.; Yang, W. T.; Deng, J. P. Optically active particles of chiral polymers. Macromol. Rapid Commun. 2013, 34(18), 1426-1445.
doi: 10.1002/marc.v34.18
Rodríguez, R.; Quiñoá, E.; Riguera, R.; Freire, F. Architecture of chiral poly(phenylacetylene)s: from compressed/highly dynamic to stretched/quasi-static helices. J. Am. Chem. Soc. 2016, 138(30), 9620-9628.
doi: 10.1021/jacs.6b04834
Zhao, Z. Y.; Wang, S.; Ye, X. C.; Zhang, J.; Wan, X. H. Planar-to-axial chirality transfer in the polymerization of phenylacetylenes. ACS Macro Lett. 2017, 6(3), 205-209.
doi: 10.1021/acsmacrolett.6b00901
Wang, S.; Chen, J. X.; Feng, X. Y.; Shi, G.; Zhang, J.; Wan, X. H. Conformation shift switches the chiral amplification of helical copoly(phenylacetylene)s from abnormal to normal " sergeants- and-soldiers” effect. Macromolecules 2017, 50(12), 4610-4615.
doi: 10.1021/acs.macromol.7b01028
Yoshio, O.; Koji, O.; Heimei, Y. Highly asymmetric selective polymerization of (RS)-α-methylbenzyl methacrylate by grignard reagent-(-)-sparteine catalyst systems. Chem. Lett. 1977, 6(6), 617-620.
doi: 10.1246/cl.1977.617
Okamoto, Y.; Urakawa, K.; Ohta, K.; Yuki, H. Asymmetric- selective polymerization of (RS)-α-methylbenzyl methacrylate. Macromolecules 1978, 11(4), 719-723.
doi: 10.1021/ma60064a020
Okamoto, Y.; Suzuki, K.; Kitayama, T.; Yuki, H.; Kageyama, H.; Miki, K.; Tanaka, N.; Kasai, N. Kinetic resolution of racemic alpha-methylbenzyl methacrylate: asymmetric selective polymeri- zation catalyzed by Grignard reagent-(-)-sparteine derivative complexes. J. Am. Chem. Soc. 1982, 104(17), 4618-4624.
doi: 10.1021/ja00381a019
Spassky, N.; Wisniewski, M.; Pluta, C.; Le Borgne, A. Highly stereoelective polymerization of rac-(D,L)-lactide with a chiral schiff's base/aluminium alkoxide initiator. Macromol. Chem. Phys. 1996, 197(9), 2627-2637.
doi: 10.1002/macp.1996.021970902
Boucard, V.; Dumas, P.; Sigwalt, P.; Guérin, P.; Fadel, A. Living stereospecific and enantioasymmetric polymerization of methylthiirane initiated by various bis(alkyl-S-cysteinato) cadmium. Eur. Polym. J. 1996, 32(4), 481-485.
doi: 10.1016/0014-3057(95)00155-7
Imai, T.; Hayakawa, K.; Satoh, T.; Kaga, H.; Kakuchi, T. Enantiomer-selective polymerization of (RS)-(phenoxymethyl) thiirane with diethylzinc/L-amino acid. J. Polym. Sci., Part A: Polym. Chem. 2002, 40(20), 3443-3448.
doi: 10.1002/(ISSN)1099-0518
Tsuji, M.; Aoki, T.; Sakai, R.; Satoh, T.; Kaga, H.; Kakuchi, T. Enantiomer-selective radical cyclopolymerization of rac-2,4- pentanediyl dimethacrylate using a ruthenium-mediated chiral atom transfer radical polymerization initiating system. J. Polym. Sci., Part A: Polym. Chem. 2004, 42(18), 4563-4569.
doi: 10.1002/(ISSN)1099-0518
Hirahata, W.; Thomas, R. M.; Lobkovsky, E. B.; Coates, G. W. Enantioselective polymerization of epoxides: a highly active and selective catalyst for the preparation of stereoregular polyethers and enantiopure epoxides. J. Am. Chem. Soc. 2008, 130(52), 17658-17659.
doi: 10.1021/ja807709j
Thomas, R. M.; Widger, P. C. B.; Ahmed, S. M.; Jeske, R. C.; Hirahata, W.; Lobkovsky, E. B.; Coates, G. W. Enantioselective epoxide polymerization using a bimetallic cobalt catalyst. J. Am. Chem. Soc. 2010, 132(46), 16520-16525.
doi: 10.1021/ja1058422
Zhu, H.; Luo, S. Z.; Wu, Z. Q. Living and enantiomer-selective polymerization of allene initiated by Ni complex containing chiral phosphine. Chin. Chem. Lett. 2018, DOI: 10.1016/j.cclet.2018.03.002.
doi: 10.1016/j.cclet.2018.03.002
Makiguchi, K.; Yamanaka, T.; Kakuchi, T.; Terada, M.; Satoh, T. Binaphthol-derived phosphoric acids as efficient chiral organocatalysts for the enantiomer-selective polymerization of rac-lactide. Chem. Commun. 2014, 50(22), 2883-2885.
doi: 10.1039/C4CC00215F
Li, H.; Ai, B. R.; Hong, M. Stereoselective ring-opening poly- merization of rac-lactide by bulky chiral and achiral N-hetero- cyclic carbenes. Chinese J. Polym. Sci. 2017, 36(2), 231-236.
Zhao, W.; Li, C. Y.; Wu, C. J.; Liu, X. L.; Mou, Z. H.; Yao, C. G.; Cui, D. M. Synthesis of ultraviolet absorption polylactide via immortal polymerization of rac-lactide initiated by a Salan- yttrium catalyst. Chinese J. Polym. Sci. 2017, 36(2), 202-206.
Zhong, Z. Y.; Dijkstra, P. J.; Feijen, J. Controlled and stereo- selective polymerization of lactide: kinetics, selectivity, and micro- structures. J. Am. Chem. Soc. 2003, 125(37), 11291-11298.
doi: 10.1021/ja0347585
Ahmed, S. M.; Poater, A.; Childers, M. I.; Widger, P. C. B.; LaPointe, A. M.; Lobkovsky, E. B.; Coates, G. W.; Cavallo, L. Enantioselective polymerization of epoxides using biaryl-linked bimetallic cobalt catalysts: a mechanistic study. J. Am. Chem. Soc. 2013, 135(50), 18901-18911.
doi: 10.1021/ja409521z
Xue, Y. X.; Zhu, Y. Y.; Gao, L. M.; He, X. Y.; Liu, N.; Zhang, W. Y.; Yin, J.; Ding, Y. S.; Zhou, H. P.; Wu, Z. Q. Air-stable (phenylbuta-1,3-diynyl)palladium(II) complexes: highly active initiators for living polymerization of isocyanides. J. Am. Chem. Soc. 2014, 136(12), 4706-4713.
doi: 10.1021/ja5004747
Chen, J.-L.; Yang, L.; Wang, Q.; Jiang, Z. Q.; Liu, N.; Yin, J.; Ding, Y. S.; Wu, Z. Q. Helix-sense-selective and enantiomer- selective living polymerization of phenyl isocyanide induced by reusable chiral lactide using achiral palladium initiator. Macromolecules 2015, 48(21), 7737-7746.
doi: 10.1021/acs.macromol.5b02124
Zhou, W.; Su, X.; Tao, M. N.; Zhu, C. Z.; Zhao, Q. J.; Zhang, J. L. Chiral sulfinamide bisphosphine catalysts: design, synthesis, and application in highly enantioselective intermolecular cross- rauhut-currier reactions. Angew. Chem. Int. Ed. 2015, 54(49), 14853-14857.
doi: 10.1002/anie.201508108
Zhang, Z. M.; Chen, P.; Li, W. B.; Niu, Y. F.; Zhao, X. L.; Zhang, J. L. A new type of chiral sulfinamide monophosphine ligands: stereodivergent synthesis and application in enantio- selective gold(I)-catalyzed cycloaddition reactions. Angew. Chem. Int. Ed. 2014, 53(17), 4350-4354.
doi: 10.1002/anie.201401067
Kajitani, T.; Okoshi, K.; Sakurai, S. I.; Kumaki, J.; Yashima, E. Helix-sense controlled polymerization of a single phenyl isocyanide enantiomer leading to diastereomeric helical polyisocyanides with opposite helix-sense and cholesteric liquid crystals with opposite twist-sense. J. Am. Chem. Soc. 2006, 128(3), 708-709.
doi: 10.1021/ja0576536
Okamoto, Y.; Urakawa, K.; Yuki, H. Asymmetric selective polymerization of racemic methacrylates with the cyclo- hexylmagnesium bromide-(-)-sparteine system. J. Polym. Sci., Polym. Chem. Ed. 1981, 19(6), 1385-1395.
doi: 10.1002/pol.1981.170190611
Horeau, A. Interactions between enantiomers in solution; effect on the rotatory power. Optical purity and enantiomeric purity. Tetrahedron Lett. 1969, 36, 3121-3124.
Jun Zhang , Zhiyao Zheng , Can Zhu . Stereochemical editing: Catalytic racemization of secondary alcohols and amines. Chinese Chemical Letters, 2024, 35(5): 109160-. doi: 10.1016/j.cclet.2023.109160
Meng Shan , Yongmei Yu , Mengli Sun , Shuping Yang , Mengqi Wang , Bo Zhu , Junbiao Chang . Bifunctional organocatalyst-catalyzed dynamic kinetic resolution of hemiketals for synthesis of chiral ketals via hydrogen bonding control. Chinese Chemical Letters, 2025, 36(1): 109781-. doi: 10.1016/j.cclet.2024.109781
Yan Li , Xinze Wang , Xue Yao , Shouyun Yu . 基于激发态手性铜催化的烯烃E→Z异构的动力学拆分——推荐一个本科生综合化学实验. University Chemistry, 2024, 39(5): 1-10. doi: 10.3866/PKU.DXHX202309053
Hailong He , Wenbing Wang , Wenmin Pang , Chen Zou , Dan Peng . Double stimulus-responsive palladium catalysts for ethylene polymerization and copolymerization. Chinese Chemical Letters, 2024, 35(7): 109534-. doi: 10.1016/j.cclet.2024.109534
Bing Niu , Honggao Huang , Liwei Luo , Li Zhang , Jianbo Tan . Coating colloidal particles with a well-defined polymer layer by surface-initiated photoinduced polymerization-induced self-assembly and the subsequent seeded polymerization. Chinese Chemical Letters, 2025, 36(2): 110431-. doi: 10.1016/j.cclet.2024.110431
Xue Zhao , Mengshan Chen , Dan Wang , Haoran Zhang , Guangzhi Hu , Yingtang Zhou . Ultrafine nano-copper derived from dopamine polymerization & synchronous adsorption achieve electrochemical purification of nitrate to ammonia in complex water environments. Chinese Chemical Letters, 2024, 35(8): 109327-. doi: 10.1016/j.cclet.2023.109327
Jian Song , Shenghui Wang , Qiuge Liu , Xiao Wang , Shuo Yuan , Hongmin Liu , Saiyang Zhang . N-Benzyl arylamide derivatives as novel and potent tubulin polymerization inhibitors against gastric cancers: Design, structure–activity relationships and biological evaluations. Chinese Chemical Letters, 2025, 36(2): 109678-. doi: 10.1016/j.cclet.2024.109678
Ruixue Liu , Xiaobing Ding , Qiwei Lang , Gen-Qiang Chen , Xumu Zhang . Enantioselective and divergent construction of chiral amino alcohols and oxazolidin-2-ones via Ir-f-phamidol-catalyzed dynamic kinetic asymmetric hydrogenation. Chinese Chemical Letters, 2025, 36(3): 110037-. doi: 10.1016/j.cclet.2024.110037
Fei Yin , Erli Yang , Xue Ge , Qian Sun , Fan Mo , Guoqiu Wu , Yanfei Shen . Coupling WO3−x dots-encapsulated metal-organic frameworks and template-free branched polymerization for dual signal-amplified electrochemiluminescence biosensing. Chinese Chemical Letters, 2024, 35(4): 108753-. doi: 10.1016/j.cclet.2023.108753
Tao Yu , Vadim A. Soloshonok , Zhekai Xiao , Hong Liu , Jiang Wang . Probing the dynamic thermodynamic resolution and biological activity of Cu(Ⅱ) and Pd(Ⅱ) complexes with Schiff base ligand derived from proline. Chinese Chemical Letters, 2024, 35(4): 108901-. doi: 10.1016/j.cclet.2023.108901
Dan-Ying Xing , Xiao-Dan Zhao , Chuan-Shu He , Bo Lai . Kinetic study and DFT calculation on the tetracycline abatement by peracetic acid. Chinese Chemical Letters, 2024, 35(9): 109436-. doi: 10.1016/j.cclet.2023.109436
Wenyi Mei , Lijuan Xie , Xiaodong Zhang , Cunjian Shi , Fengzhi Wang , Qiqi Fu , Zhenjiang Zhao , Honglin Li , Yufang Xu , Zhuo Chen . Design, synthesis and biological evaluation of fluorescent derivatives of ursolic acid in living cells. Chinese Chemical Letters, 2024, 35(5): 108825-. doi: 10.1016/j.cclet.2023.108825
Ruilong Geng , Lingzi Peng , Chang Guo . Dynamic kinetic stereodivergent transformations of propargylic ammonium salts via dual nickel and copper catalysis. Chinese Chemical Letters, 2024, 35(8): 109433-. doi: 10.1016/j.cclet.2023.109433
Ling Tang , Yan Wan , Yangming Lin . Lowering the kinetic barrier via enhancing electrophilicity of surface oxygen to boost acidic oxygen evolution reaction. Chinese Journal of Structural Chemistry, 2024, 43(11): 100345-100345. doi: 10.1016/j.cjsc.2024.100345
Lilin Song , Mengru Sun , Yuqing Song , Feng Zhang , Bei Zhao , Hairong Zeng , Jinhui Shi , Huixin Liu , Shanshan Zhao , Tian Tian , Heng Yin , Guangbo Ge . Rationally engineered IR-783 octanoate as an enzyme-activatable fluorogenic tool for functional imaging of hNotum in living systems. Chinese Chemical Letters, 2024, 35(11): 109601-. doi: 10.1016/j.cclet.2024.109601
Hui Zhang , Rong Feng , Wanyi Yu , Hongbei Wei , Tianhong Wu , Peng Zhang , Wenhai Bian , Xin Li , Di Gao , Guojun Weng , Zhe Yang , Tony D. James , Xiaolong Sun . Evaluating the global thiols redox state in living cells using a reducing sulfur species responsive fluorescence switching platform. Chinese Chemical Letters, 2025, 36(4): 110528-. doi: 10.1016/j.cclet.2024.110528
Zhixiao Xiong , Shanni Qiu , Yuyu Wang , Houna Duan , Yi Xiao , Yufang Xu , Weiping Zhu , Xuhong Qian . Photocalibrated NO release from the zinc ion fluorescent probe based on naphthalimide and its application in living cells. Chinese Chemical Letters, 2025, 36(4): 110002-. doi: 10.1016/j.cclet.2024.110002
Yongheng Ren , Yang Chen , Hongwei Chen , Lu Zhang , Jiangfeng Yang , Qi Shi , Lin-Bing Sun , Jinping Li , Libo Li . Electrostatically driven kinetic Inverse CO2/C2H2 separation in LTA-type zeolites. Chinese Journal of Structural Chemistry, 2024, 43(10): 100394-100394. doi: 10.1016/j.cjsc.2024.100394
Yudi Cheng , Xiao Wang , Jiao Chen , Zihan Zhang , Jiadong Ou , Mengyao She , Fulin Chen , Jianli Li . A near-infrared fluorescent probe for visualizing transformation pathway of Cys/Hcy and H2S and its applications in living system. Chinese Chemical Letters, 2024, 35(5): 109156-. doi: 10.1016/j.cclet.2023.109156
Han-Min Wang , Yan-Chen Li , Lu-Lu Sun , Ming-Ye Tang , Jia Liu , Jiahao Cai , Lei Dong , Jia Li , Yi Zang , Hai-Hao Han , Xiao-Peng He . Protein-encapsulated long-wavelength fluorescent probe hybrid for imaging lipid droplets in living cells and mice with non-alcoholic fatty liver. Chinese Chemical Letters, 2024, 35(11): 109603-. doi: 10.1016/j.cclet.2024.109603