Citation: Chonggang Wang, Shudan Chen, Hao Zhou, Jinlou Gu, Aiguo Hu. Palladium-catalyzed Cycloaromatization Polymerization of Enediynes[J]. Chinese Journal of Polymer Science, ;2018, 36(2): 237-243. doi: 10.1007/s10118-018-2088-9 shu

Palladium-catalyzed Cycloaromatization Polymerization of Enediynes

Shanghai Key Laboratory of Advanced Polymeric Materials, School of Materials Science and Engineering, East China University of Science and Technology, Shanghai 200237, China

Corresponding author: Aiguo Hu, hagmhsn@ecust.edu.cn
Received Date: 29 September 2017
Accepted Date: 6 November 2017
Available Online: 1 December 2017

Bergman cyclization has shown great promise in constructing conjugated polymers. However, the application of this reaction in polymer science is still limited due to the harsh reaction condition and ill-defined structure of the achieved polymers. To this end, the cycloaromatization polymerization of enediynes catalyzed by a series of transition metal catalysts is investigated in this work, by taking advantage of the coordination chemistry of the enediyne with the transition metal complexes. According to the nuclear magnetic resonance (NMR), Fourier transform infrared (FTIR), ultraviolet-visble (UV-Vis) spectroscopies and matrix-assisted laser desorption/ionization time-offlight mass spectrometry (MALDI-TOF MS) analysis, the cycloaromatization polymerization of enediynes proceeds under milder conditions and in a more controlled manner in the presence of palladium(Ⅱ) complexes, giving structurally regulated conjugated polymers in high yields.
- Transition metal catalysis,
- Enediyne,
- Polymerization,
- Cycloaromatization,
- Bergman cyclization
1. [1]
  Alabugin I. V., Manoharan M.. Radical-anionic cyclizations of enediynes:remarkable effects of benzannelation and remote substituents on cyclorearomatization reactions[J]. J. Am. Chem. Soc., 2003,125(15):4495-4509. doi: 10.1021/ja029664u
2. [2]
  Mohamed R. K., Peterson P. W., Alabugin I. V.. Concerted reactions that produce diradicals and zwitterions:electronic, steric, conformational, and kinetic control of cycloaromatization processes[J]. Chem. Rev., 2013,113(9):7089-7129. doi: 10.1021/cr4000682
3. [3]
  Xiao Y., Hu A.. Bergman cyclization in polymer chemistry and material science[J]. Macromol. Rapid Commun., 2011,32(21):1688-1698. doi: 10.1002/marc.201100378
4. [4]
  Chen S., Hu A.. Recent advances of the Bergman cyclization in polymer science[J]. Sci. China:Chem., 2015,58(11):1710-1723. doi: 10.1007/s11426-015-5460-4
5. [5]
  Sun Q., Zhang C., Li Z., Kong H., Tan Q., Hu A., Xu W.. On-surface formation of one-dimensional polyphenylene through Bergman cyclization[J]. J. Am. Chem. Soc., 2013,135(23):8448-8451. doi: 10.1021/ja404039t
6. [6]
  Biggins J. B., Onwueme K. C., Thorson J. S.. Resistance to enediyne antitumor antibiotics by calC self-sacrifice[J]. Science, 2003,301(5639):1537-1541. doi: 10.1126/science.1086695
7. [7]
  Kovalenko S. V., Peabody S., Manoharan M., Clark R. J., Alabugin I. V.. 5-Exo-dig radical cyclization of enediynes:the first synthesis of tin-substituted benzofulvenes[J]. Org. Lett., 2004,6(14):2457-2460. doi: 10.1021/ol049122c
8. [8]
  Byers P. M., Rashid J. I., Mohamed R. K., Alabugin I. V.. Polyaromatic ribbon/benzofuran fusion via consecutive endo cyclizations of enediynes[J]. Org. Lett., 2012,14(23):6032-6035. doi: 10.1021/ol302922t
9. [9]
  Alabugin I. V., Gilmore K., Patil S., Manoharan M., Kovalenko S. V., Clark R. J., Ghiviriga I.. Radical cascade transformations of tris(o-aryleneethynylenes) into substituted Benzo[J]. J. Am. Chem. Soc., 2008,130(34):11535-11545. doi: 10.1021/ja8038213
10. [10]
  Perrin C. L., Rodgers B. L., O'Connor J. M.. Nucleophilic addition to ap-benzyne derived from an enediyne:a new mechanism for halide incorporation into biomolecules[J]. J. Am. Chem. Soc., 2007,129(15):4795-4799. doi: 10.1021/ja070023e
11. [11]
  Gulevskaya A. V., Tyaglivy A. S.. Nucleophilic cyclizations of enediynes as a method for polynuclear heterocycle synthesis[J]. Chem. Heterocycl. Compd., 2012,48(1):82-94. doi: 10.1007/s10593-012-0972-8
12. [12]
  Perrin C. L., Reyes-Rodríguez G. J.. Selectivity and isotope effects in hydronation of a naked aryl anion[J]. J. Am. Chem. Soc., 2014,136(43):15263-15269. doi: 10.1021/ja507517g
13. [13]
  Gulevskaya A. V., Lazarevich R. Y., Pozharskii A. F.. Electrophilic cyclizations of 2, 3-dialkynylquinoxalines and 1, 2-dialkynylbenzenes:a comparative study[J]. Tetrahedron, 2013,69(2):910-917. doi: 10.1016/j.tet.2012.10.098
14. [14]
  Gulevskaya A. V., Lazarevich R. Y.. Cyclizations of enediynes under the action of electrophiles[J]. Chem. Heterocycl. Compd., 2013,49(1):116-139. doi: 10.1007/s10593-013-1234-0
15. [15]
  Chen S., Li Q., Sun S., Ding Y., Hu A.. A novel approach toward polyfulvene:cationic polymerization of enediynes[J]. Macromolecules, 2017,50(2):534-541. doi: 10.1021/acs.macromol.6b02321
16. [16]
  Wang Y., Finn M.. Organometallic diradical cycloaromatization reaction[J]. J. Am. Chem. Soc., 1995,117(30):8045-8046. doi: 10.1021/ja00135a035
17. [17]
  Taduri B. P., Ran Y. F., Huang C. W., Liu R. S.. Platinum-catalyzed aromatization of enediynes via a C-H bond insertion of tethered alkanes[J]. Org. Lett., 2006,8(5):883-886. doi: 10.1021/ol052962m
18. [18]
  O'Connor J. M., Friese S. J., Tichenor M.. Ruthenium-mediated cycloaromatization of acyclic enediynes and dienynes at ambient temperature[J]. J. Am. Chem. Soc., 2002,124(14):3506-3507. doi: 10.1021/ja017873t
19. [19]
  Larsen M. H., Houk K. N., Hashmi A. S. K.. Dual gold catalysis:stepwise catalyst transfer via dinuclear clusters[J]. J. Am. Chem. Soc., 2015,137(33):10668-10676. doi: 10.1021/jacs.5b05773
20. [20]
  Basak A., Mandal S., Bag S. S.. Chelation-controlled Bergman cyclization:synthesis and reactivity of enediynyl ligands[J]. Chem. Rev., 2003,103(10):4077-4094. doi: 10.1021/cr020069k
21. [21]
  O'Connor J. M., Friese S. J., Rodgers B. L.. A transition-metal-catalyzed enediyne cycloaromatization[J]. J. Am. Chem. Soc., 2005,127(47):16342-16343. doi: 10.1021/ja050060a
22. [22]
  Zhu B., Qian G., Xiao Y., Deng S., Wang M., Hu A.. A convergence of photo-Bergman cyclization and intramolecular chain collapse towards polymeric nanoparticles[J]. J. Polym. Sci., Part A:Polym. Chem., 2011,49(24):5330-5338. doi: 10.1002/pola.v49.24
23. [23]
  Manabe T., Yanagi S.-i., Ohe K., Uemura S.. New examples of 1, 6-and 1, 7-hydrogen transfer promoted by an α-silyl group in Rhodium(Ⅰ)-catalyzed radical reactions of acyclic enediynes[J]. Organometallics, 1998,17(14):2942-2944. doi: 10.1021/om980143i
24. [24]
  Odedra A., Wu C. J., Pratap T. B., Huang C. W., Ran Y. F., Liu R. S.. Ruthenium-catalyzed aromatization of enediynes via highly regioselective nucleophilic additions on a pi-alkyne functionality. A useful method for the synthesis of functionalized benzene derivatives[J]. J. Am. Chem. Soc., 2005,127(10):3406-3412.
25. [25]
  Naoe S., Suzuki Y., Hirano K., Inaba Y., Oishi S., Fujii N., Ohno H.. Gold(Ⅰ)-catalyzed regioselective inter-/intramolecular addition cascade of di-and triynes for direct construction of substituted naphthalenes[J]. J. Org. Chem., 2012,77(11):4907-4916. doi: 10.1021/jo300771f
26. [26]
  Nösel P., Müller V., Mader S., Moghimi S., Rudolph M., Braun I., Rominger F., Hashmi A. S. K.. Gold-catalyzed hydroarylating cyclization of 1, 2-bis(2-iodoethynyl)benzenes[J]. Adv. Synth. Catal., 2015,357(2-3):500-506. doi: 10.1002/adsc.201400749
27. [27]
  Hashmi A. S., Wieteck M., Braun I., Rudolph M., Rominger F.. Gold vinylidene complexes:intermolecular C(sp(3))H insertions and cyclopropanations pathways[J]. Angew. Chem. Int. Ed., 2012,51(42):10633-10637. doi: 10.1002/anie.201204015
28. [28]
  dos Passos Gomes G., Alabugin I. V.. Drawing catalytic power from charge separation:stereoelectronic and zwitterionic assistance in the Au(Ⅰ)-catalyzed Bergman cyclization[J]. J. Am. Chem. Soc., 2017,139(9):3406-3416. doi: 10.1021/jacs.6b11054
29. [29]
  Sun S., Dong L., Song D., Huang B., Hu A.. Synthesis of polyphenylenes through bergman cyclization of enediynes with long chain alkyl groups[J]. Chinese J. Polym. Sci., 2015,33(1):184-191. doi: 10.1007/s10118-015-1566-6
30. [30]
  Cheng X., Ma J., Zhi J., Yang X., Hu A.. Synthesis of novel "rod-coil" brush polymers with conjugated backbones through Bergman cyclization[J]. Macromolecules, 2010,43(2):909-913. doi: 10.1021/ma902176j
31. [31]
  Johnson J. P., Bringley D. A., Wilson E. E., Lewis K. D., Beck L. W., Matzger A. J.. Comparison of "polynaphthalenes" prepared by two mechanistically distinct routes[J]. J. Am. Chem. Soc., 2003,125(48):14708-14709. doi: 10.1021/ja035695t
32. [32]
  Warner B. P., Millar S. P., Broene R. D., Buchwald S. L.. Controlled acceleration and inhibition of Bergman cyclization by metal chlorides[J]. Science, 1995,269(5225):814-816. doi: 10.1126/science.269.5225.814
33. [33]
  Kaneko T., Takahashi M., Hirama M.. Benzannelation alters the rate limiting step in enediyne cycloaromatization[J]. Tetrahedron Lett., 1999,40(10):2015-2018. doi: 10.1016/S0040-4039(99)00105-7
34. [34]
  Grissom J. W., Calkins T. L., McMillen H. A., Jiang Y.. Determination of the activation parameters for the Bergman cyclization of aromatic enediynes[J]. J. Org. Chem., 1994,59(19):5833-5835. doi: 10.1021/jo00098a055
35. [35]
  Zeidan T. A., Kovalenko S. V., Manoharan M., Alabugin I. V.. Ortho effect in the Bergman cyclization:comparison of experimental approaches and dissection of cycloaromatization kinetics[J]. J. Org. Chem., 2006,71(3):962-975. doi: 10.1021/jo0520801
36. [36]
  Nicolau K. C., Zuccarello G., Ogawa Y., Schweiger E. J., Kumazawa T.. Cyclic conjugated enediynes related to calicheamicins and esperamicins:calculations, synthesis, and properties[J]. J. Am. Chem. Soc., 1988,110(14):4866-4868. doi: 10.1021/ja00222a077
1. [1]
  Kongchuan Wu , Dandan Lu , Jianbin Lin , Ting-Bin Wen , Wei Hao , Kai Tan , Hui-Jun Zhang . Elucidating ligand effects in rhodium(Ⅲ)-catalyzed arene–alkene coupling reactions. Chinese Chemical Letters, 2024, 35(5): 108906-. doi: 10.1016/j.cclet.2023.108906
2. [2]
  Daheng Wen , Weiwei Fang , Yongmei Liu , Tao Tu . Valorization of carbon dioxide with alcohols. Chinese Chemical Letters, 2024, 35(7): 109394-. doi: 10.1016/j.cclet.2023.109394
3. [3]
  Laiying Zhang , Yinghuan Wu , Yazi Yu , Yecheng Xu , Haojie Zhang , Weitai Wu . Innovation and Practice of Polymer Chemistry Experiment Teaching for Non-Polymer Major Students of Chemistry: Taking the Synthesis, Solution Property, Optical Performance and Application of Thermo-Sensitive Polymers as an Example. University Chemistry, 2024, 39(4): 213-220. doi: 10.3866/PKU.DXHX202310126
4. [4]
  Yan Li , Xinze Wang , Xue Yao , Shouyun Yu . Kinetic Resolution Enabled by Photoexcited Chiral Copper Complex-Mediated Alkene E→Z Isomerization: A Comprehensive Chemistry Experiment for Undergraduate Students. University Chemistry, 2024, 39(5): 1-10. doi: 10.3866/PKU.DXHX202309053
5. [5]
  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
6. [6]
  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
7. [7]
  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
8. [8]
  Yuhao Guo , Na Li , Tingjiang Yan . Tandem catalysis for photoreduction of CO2 into multi-carbon fuels on atomically thin dual-metal phosphochalcogenides. Chinese Journal of Structural Chemistry, 2024, 43(7): 100320-100320. doi: 10.1016/j.cjsc.2024.100320
9. [9]
  Yatian Deng , Dao Wang , Jinglan Cheng , Yunkun Zhao , Zongbao Li , Chunyan Zang , Jian Li , Lichao Jia . A new popular transition metal-based catalyst: SmMn₂O₅ mullite-type oxide. Chinese Chemical Letters, 2024, 35(8): 109141-. doi: 10.1016/j.cclet.2023.109141
10. [10]
  Boqiang Wang , Yongzhuo Xu , Jiajia Wang , Muyang Yang , Guo-Jun Deng , Wen Shao . Transition-metal free trifluoromethylimination of alkenes enabled by direct activation of N-unprotected ketimines. Chinese Chemical Letters, 2024, 35(9): 109502-. doi: 10.1016/j.cclet.2024.109502
11. [11]
  Shuanglin TIAN , Tinghong GAO , Yutao LIU , Qian CHEN , Quan XIE , Qingquan XIAO , Yongchao LIANG . First-principles study of adsorption of Cl₂ and CO gas molecules by transition metal-doped g-GaN. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1189-1200. doi: 10.11862/CJIC.20230482
12. [12]
  Pengfei Zhang , Qingxue Ma , Zhiwei Jiang , Xiaohua Xu , Zhong Jin . Transition-metal-catalyzed remote meta-C—H alkylation and alkynylation of aryl sulfonic acids enabled by an indolyl template. Chinese Chemical Letters, 2024, 35(8): 109361-. doi: 10.1016/j.cclet.2023.109361
13. [13]
  Yaping Zhang , Wei Zhou , Mingchun Gao , Tianqi Liu , Bingxin Liu , Chang-Hua Ding , Bin Xu . Oxidative cyclization of allyl compounds and isocyanide: A facile entry to polysubstituted 2-cyanopyrroles. Chinese Chemical Letters, 2024, 35(4): 108836-. doi: 10.1016/j.cclet.2023.108836
14. [14]
  Yi-Fan Wang , Hao-Yun Yu , Hao Xu , Ya-Jie Wang , Xiaodi Yang , Yu-Hui Wang , Ping Tian , Guo-Qiang Lin . Rhodium(Ⅲ)-catalyzed diastereo- and enantioselective hydrosilylation/cyclization reaction of cyclohexadienone-tethered α, β-unsaturated aldehydes. Chinese Chemical Letters, 2024, 35(9): 109520-. doi: 10.1016/j.cclet.2024.109520
15. [15]
  Conghui Wang , Lei Xu , Zhenhua Jia , Teck-Peng Loh . Recent applications of macrocycles in supramolecular catalysis. Chinese Chemical Letters, 2024, 35(4): 109075-. doi: 10.1016/j.cclet.2023.109075
16. [16]
  Wei Chen , Pieter Cnudde . A minireview to ketene chemistry in zeolite catalysis. Chinese Journal of Structural Chemistry, 2024, 43(11): 100412-100412. doi: 10.1016/j.cjsc.2024.100412
17. [17]
  Xinghui Yao , Zhouyu Wang , Da-Gang Yu . Sustainable electrosynthesis: Enantioselective electrochemical Rh(III)/chiral carboxylic acid-catalyzed oxidative CH cyclization coupled with hydrogen evolution reaction. Chinese Chemical Letters, 2024, 35(9): 109916-. doi: 10.1016/j.cclet.2024.109916
18. [18]
  Yu Mao , Yilin Liu , Xiaochen Wang , Shengyang Ni , Yi Pan , Yi Wang . Acylfluorination of enynes via phosphine and silver catalysis. Chinese Chemical Letters, 2024, 35(8): 109443-. doi: 10.1016/j.cclet.2023.109443
19. [19]
  Ke Zhang , Sheng Zuo , Pengyuan You , Tong Ru , Fen-Er Chen . Palladium-catalyzed stereoselective decarboxylative [4 + 2] cyclization of 2-methylidenetrimethylene carbonates with pyrrolidone-derived enones: Straightforward access to chiral tetrahydropyran-fused spiro-pyrrolidine-2,3-diones. Chinese Chemical Letters, 2024, 35(6): 109157-. doi: 10.1016/j.cclet.2023.109157
20. [20]
  Ning LI , Siyu DU , Xueyi WANG , Hui YANG , Tao ZHOU , Zhimin GUAN , Peng FEI , Hongfang MA , Shang JIANG . Preparation and efficient catalysis for olefins epoxidation of a polyoxovanadate-based hybrid. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 799-808. doi: 10.11862/CJIC.20230372

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(684)
HTML views(19)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142