Citation: Pun Sai Ho, Miao Qian. Introduction of Eight-Membered Rings to Polycyclic Arenes by Ring Expansion[J]. Chinese Journal of Organic Chemistry, ;2020, 40(10): 3347-3353. doi: 10.6023/cjoc202005033 shu

Introduction of Eight-Membered Rings to Polycyclic Arenes by Ring Expansion

Pun Sai Ho ,
Miao Qian ^,

Department of Chemistry, the Chinese University of Hong Kong, Hong Kong

Corresponding author: Miao Qian, miaoqian@cuhk.edu.hk
Received Date: 14 May 2020
Revised Date: 26 June 2020
Available Online: 15 July 2020
Fund Project: Project supported by the Research Grants Council of Hong Kong (No. GRF 14300919)the Research Grants Council of Hong Kong GRF14300919

Figures(5)

A synthetic strategy based on a ring expansion reaction to introduce eight-membered rings into polycyclic aromatic frameworks is reported. The octagon-embedded hexabenzocoronene synthesized with this strategy features a saddle-shaped polycyclic framework as revealed by the single crystal X-ray crystallography.
- eight-membered ring,
- polycyclic arenes,
- ring expansion
1. [1]
  (a) Narita, A.; Wang, X.-Y.; Feng, X.; Müllen, K. Chem. Soc. Rev. 2015, 44, 6616.
  (b) Segawa, Y.; Ito, H.; Itami, K. Nat. Rev. Mater. 2016, 1, 15002.
  (c) Rickhaus, M.; Mayor, M.; Juríček, M. Chem. Soc. Rev. 2017, 46, 1643.
  (d) Cruz, C. M.; Castro-Fernández, S.; Maçôas, E.; Millán, A.; Campaña, A. G. Synlett 2019, 30, 997.
2. [2]
  Bharat; Bhola, R.; Bally, T.; Valente, A.; Cyrański, M. K.; Dobrzycki, Ł.; Spain, S. M.; Rempała, P.; Chin, M. R.; King, B. T. Angew. Chem., Int. Ed. 2010, 49, 399. doi: 10.1002/anie.200905633
3. [3]
  Barth, W. E.; Lawton, R. G. J. Am. Chem. Soc. 1966, 88, 380. doi: 10.1021/ja00954a049
4. [4]
  Luo, J.; Xu, X.; Mao, R.; Miao, Q. J. Am. Chem. Soc. 2012, 134, 13796. doi: 10.1021/ja3054354
5. [5]
  (a) Kawasumi, K.; Zhang, Q.; Segawa, Y.; Scott, L. T.; Itami, K. Nat. Chem. 2013, 5, 739.
  (b) Márquez, I. R.; Fuentes, N.; Cruz, C. M.; Puente-Muñoz, V.; Sotorrios, L.; Marcos, M. L.; Choquesillo-Lazarte, D.; Biel, B.; Crovetto, L.; Gómez-Bengoa, E.; González, M. T.; Martin, R.; Cuerva, J. M.; Campaña, A. G. Chem. Sci. 2017, 8, 1068.
  (c) Fukui, N.; Kim, T.; Kim, D.; Osuka, A. J. Am. Chem. Soc. 2017, 139, 9075.
  (d) Gu, X.; Li, H.; Shan, B.; Liu, Z.; Miao, Q. Org. Lett. 2017, 19, 2246.
  (e) Oki, K.; Takase, M.; Mori, S.; Shiotari, A.; Sugimoto, Y.; Ohara, K.; Okujima, T.; Uno, H. J. Am. Chem. Soc. 2018, 140, 10430.
  (f) Fernández-García, J. M.; Evans, P. J.; Medina Rivero, S.; Fernández, I.; García-Fresnadillo, D.; Perles, J.; Casado, J.; Martín, N. J. Am. Chem. Soc. 2018, 140, 17188.
  (g) Farrell, J. M.; Grande, V.; Schmidt, D.; Würthner, F. Angew. Chem. 2019, 131, 16656.
6. [6]
  Pun, S. H.; Chan, C. K.; Luo, J.; Liu, Z.; Miao, Q. Angew. Chem., Int. Ed. 2018, 57, 1581. doi: 10.1002/anie.201711437
7. [7]
  (a) Feng, C.-N.; Kuo, M.-Y.; Wu, Y.-T. Angew. Chem., Int. Ed. 2013, 52, 7791.
  (b) Sakamoto, Y.; Suzuki, T. J. Am. Chem. Soc. 2013, 135, 14074.
  (c) Miller, R. W.; Duncan, A. K.; Schneebeli, S. T.; Gray, D. L.; Whalley, A. C. Chem. Eur. J. 2014, 20, 3705.
  (d) Chen, F.; Hong, Y. S.; Shimizu, S.; Kim, D.; Tanaka, T.; Osuka, A. Angew. Chem., Int. Ed. 2015, 54, 10639.
  (e) Miller, R. W.; Averill, S. E.; Van Wyck, S. J.; Whalley, A. C. J. Org. Chem. 2016, 81, 12001.
  (f) Cheung, K. Y.; Chan, C. K.; Liu, Z.; Miao, Q. Angew. Chem., Int. Ed. 2017, 56, 9003.
  (g) Pun, S. H.; Wang, Y.; Chu, M.; Chan, C. K.; Li, Y.; Liu, Z.; Miao, Q. J. Am. Chem. Soc. 2019, 141, 9680.
8. [8]
  Mackay, A. L.; Terrones, H. Nature 1991, 352, 762.
9. [9]
  Kim, K.; Lee, T.; Kwon, Y.; Seo, Y.; Song, J.; Park, J.; Lee, H.; Park, J. Y.; Ihee, H.; Cho, S. J.; Ryoo, R. Nature 2016, 535, 131. doi: 10.1038/nature18284
10. [10]
  Braun, E.; Lee, Y.; Moosavi, S. M.; Barthel, S.; Mercado, R.; Baburin, I. A.; Proserpio, D. M.; Smit, B. Proc. Natl. Acad. Sci. U. S. A. 2018, 115, E8116. doi: 10.1073/pnas.1805062115
11. [11]
  (a) Pun, S. H.; Miao, Q. Acc. Chem. Res. 2018, 51, 1630.
  (b) Márquez, I. R.; Castro-Fernández, S.; Millán, A.; Campaña, A. G. Chem. Commun. 2018, 54, 6705.
  (c) Stępień, M.; Majewski, M. A. Angew. Chem., Int. Ed. 2019, 58, 86.
12. [12]
  Christoph, H.; Grunenberg, J.; Hopf, H.; Dix, I.; Jones, P. G.; Scholtissek, M.; Maier, G. Chem. Eur. J. 2008, 14, 5604. doi: 10.1002/chem.200701837
13. [13]
  (a) Wong, H. N. C.; Sondheimer, F. Tetrahedron 1981, 37, 99.
  (b) Wong, H. N. C. Acc. Chem. Res. 1989, 22, 145.
14. [14]
  (a) Müller, M.; Iyer, V. S.; Kübel, C.; Enkelmann, V.; Müllen, K. Angew. Chem., Int. Ed. Engl. 1997, 36, 1607.
  (b) Nobusue, S.; Fujita, K.; Tobe, Y. Org. Lett. 2017, 19, 3227.
  (c) Tamoto, A.; Aratani, N.; Yamada, H. Chem. Eur. J. 2017, 23, 16388.
15. [15]
  Cheung, K. Y.; Xu, X.; Miao, Q. J. Am. Chem. Soc. 2015, 137, 3910. doi: 10.1021/jacs.5b00403
16. [16]
  Resendiz, M. J. E.; Garcia-Garibay, M. A. Org. Lett. 2005, 7, 371. doi: 10.1021/ol0480527
17. [17]
  (a) Grzybowski, M.; Skonieczny, K.; Butenschön, H.; Gryko, D. T. Angew. Chem. Int. Ed. 2013, 52, 9900.
  (b) Grzybowski, M.; Sadowski, B.; Butenschön, H.; Gryko, D. Angew. Chem., Int. Ed. 2019, 59, 2998.
18. [18]
  (a) Scholl, R.; Mansfeld, J. Ber. Dtsch. Chem. Ges. 1910, 43, 1734.
  (b) Scholl, R.; Seer, C.; Weitzenböck, R. Ber. Dtsch. Chem. Ges. 1910, 43, 2202.
19. [19]
  Zhai, L.; Shukla, R.; Rathore, R. Org. Lett. 2009, 11, 3474. doi: 10.1021/ol901331p
20. [20]
  (a) Plunkett, K. N.; Godula, K.; Nuckolls, C.; Tremblay, N.; Whalley, A. C.; Xiao, S. Org. Lett. 2009, 11, 2225.
  (b) Zhai, L.; Shukla, R.; Wadumethrige, S. H.; Rathore, R. J. Org. Chem. 2010, 75, 4748.
  (c) Ip, H.-W.; Ng, C.-F.; Chow, H.-F.; Kuck, D. J. Am. Chem. Soc. 2016, 138, 13778.
21. [21]
  (a) Hennig, R.; Metz, P. Angew. Chem. Int. Ed. 2009, 48, 1157.
  (b) Sakai, T.; Ito, S.; Furuta, H.; Kawahara, Y.; Mori, Y. Org. Lett. 2012, 14, 4564.
22. [22]
  (a) Chaffins, S.; Brettreich, M.; Wudl, F. Synthesis 2002, 9, 1191.
  (b) Sletten, E. M.; Nakamura, H.; Jewett, J. C.; Bertozzi, C. R. J. Am. Chem. Soc. 2010, 132, 11799.
23. [23]
  King, B. T.; Kroulik, J.; Robertson, C. R.; Rempala, P.; Hilton, C. L.; Korinek, J. D.; Gortari, L. M. J. Org. Chem. 2007, 72, 2279. doi: 10.1021/jo061515x
24. [24]
  CCDC2003773 contains the crystallographic data for 9. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre.
25. [25]
  Anslyn, E. V.; Dougherty, D. A. Modern Physical Organic Chemistry, University Science Books, Sausalito, 2004, Chapter 1, p. 22.
26. [26]
  The commonly used formal potential of the redox couple of ferrocenium/ferrocene (F_c⁺/F_c) in the Fermi scale is -5.1 eV, which is calculated on the basis of an approximation neglecting solvent effects using a work function of 4.46 eV for the normal hydrogen electrode (NHE) and an electrochemical potential of 0.64 V for (F_c⁺/F_c) versus NHE. See: Cardona, C. M.; Li, W.; Kaifer, A. E.; Stockdale, D.; Bazan, G. C. Adv. Mater. 2011, 23, 2367.
27. [27]
  (a) Wu, J.; Pisula, W.; Müllen, K. Chem. Rev. 2007, 107, 718.
  (b) Zhi, L.; Müllen, K. J. Mater. Chem. 2008, 18, 1472.
1. [1]
  Jing-Qi Tao , Shuai Liu , Tian-Yu Zhang , Hong Xin , Xu Yang , Xin-Hua Duan , Li-Na Guo . Photoinduced copper-catalyzed alkoxyl radical-triggered ring-expansion/aminocarbonylation cascade. Chinese Chemical Letters, 2024, 35(6): 109263-. doi: 10.1016/j.cclet.2023.109263
2. [2]
  Wenling Yuan , Fengli Li , Zhe Chen , Qiaoxin Xu , Zhenhua Guan , Nanyu Yao , Zhengxi Hu , Junjun Liu , Yuan Zhou , Ying Ye , Yonghui Zhang . AbnI: An α-ketoglutarate-dependent dioxygenase involved in brassicicene CH functionalization and ring system rearrangement. Chinese Chemical Letters, 2024, 35(5): 108788-. doi: 10.1016/j.cclet.2023.108788
3. [3]
  Yue Sun , Liming Yang , Yaohang Cheng , Guanghui An , Guangming Li . Pd(I)-catalyzed ring-opening arylation of cyclopropyl-α-aminoamides: Access to α-ketoamide peptidomimetics. Chinese Chemical Letters, 2024, 35(6): 109250-. doi: 10.1016/j.cclet.2023.109250
4. [4]
  Qiuyun Li , Yannan Zhu , Yining Wang , Gang Qi , Wen-Juan Hao , Kelu Yan , Bo Jiang . Catalytic CH activation-initiated transdiannulation: An oxygen transfer route to ring-fluorinated tricyclic γ-lactones. Chinese Chemical Letters, 2024, 35(9): 109494-. doi: 10.1016/j.cclet.2024.109494
5. [5]
  Wenyu Gao , Liming Zhang , Chuang Zhao , Lixiang Liu , Xingran Yang , Jinbo Zhao . Controlled semi-Pinacol rearrangement on a strained ring: Efficient access to multi-substituted cyclopropanes by group migration strategy. Chinese Chemical Letters, 2024, 35(9): 109447-. doi: 10.1016/j.cclet.2023.109447
6. [6]
  Rong-Nan Yi , Wei-Min He . Visible light/copper catalysis enabled radial type ring-opening of sulfonium salts. Chinese Chemical Letters, 2025, 36(4): 110787-. doi: 10.1016/j.cclet.2024.110787
7. [7]
  Qinghong Zhang , Qiao Zhao , Xiaodi Wu , Li Wang , Kairui Shen , Yuchen Hua , Cheng Gao , Yu Zhang , Mei Peng , Kai Zhao . Visible-light-induced ring-opening cross-coupling of cycloalcohols with vinylazaarenes and enones via β-C-C scission enabled by proton-coupled electron transfer. Chinese Chemical Letters, 2025, 36(2): 110167-. doi: 10.1016/j.cclet.2024.110167
8. [8]
  Peiyan Zhu , Yanyan Yang , Hui Li , Jinhua Wang , Shiqing Li . Rh(Ⅲ)‐Catalyzed sequential ring‐retentive/‐opening [4 + 2] annulations of 2H‐imidazoles towards full‐color emissive imidazo[5,1‐a]isoquinolinium salts and AIE‐active non‐symmetric 1,1′‐biisoquinolines. Chinese Chemical Letters, 2024, 35(10): 109533-. doi: 10.1016/j.cclet.2024.109533
9. [9]
  Juan Guo , Mingyuan Fang , Qingsong Liu , Xiao Ren , Yongqiang Qiao , Mingju Chao , Erjun Liang , Qilong Gao . Zero thermal expansion in Cs₂W₃O₁₀. Chinese Chemical Letters, 2024, 35(7): 108957-. doi: 10.1016/j.cclet.2023.108957
10. [10]
  Jingyuan Yang , Xinyu Tian , Liuzhong Yuan , Yu Liu , Yue Wang , Chuandong Dou . Enhancing stability of diradical polycyclic hydrocarbons via P=O-attaching. Chinese Chemical Letters, 2024, 35(8): 109745-. doi: 10.1016/j.cclet.2024.109745
11. [11]
  Jie Yang , Xin-Yue Lou , Dihua Dai , Jingwei Shi , Ying-Wei Yang . Desymmetrized pillar[8]arenes: High-yield synthesis, functionalization, and host-guest chemistry. Chinese Chemical Letters, 2025, 36(1): 109818-. doi: 10.1016/j.cclet.2024.109818
12. [12]
  Shuai Liang , Wen-Jing Jiang , Ji-Xiang Hu . Achieving colossal anisotropic thermal expansion via synergism of spin crossover and rhombus deformation. Chinese Journal of Structural Chemistry, 2025, 44(2): 100430-100430. doi: 10.1016/j.cjsc.2024.100430
13. [13]
  Xixian Sun , Shengke Li , Ruibing Wang , Leyong Wang . Functional macrocyclic arenes with active binding sites inside cavity for biomimetic molecular recognition. Chinese Chemical Letters, 2025, 36(4): 110806-. doi: 10.1016/j.cclet.2024.110806
14. [14]
  Xueru Zhao , Aopu Wang , Shimin Wang , Zhijie Song , Li Ma , Li Shao . Adsorption and visual detection of nitro explosives by pillar[n]arenes-based host–guest interactions. Chinese Chemical Letters, 2025, 36(4): 110205-. doi: 10.1016/j.cclet.2024.110205
15. [15]
  Zhengyi Shi , Jie Yin , Yang Xiao , Zhangrong Hou , Fei Song , Jianping Wang , Qingyi Tong , Changxing Qi , Yonghui Zhang . Unprecedented sesquiterpene-polycyclic polyprenylated acylphloroglucinol adduct against acute myeloid leukemia via inhibiting mitochondrial complex Ⅴ. Chinese Chemical Letters, 2024, 35(10): 109458-. doi: 10.1016/j.cclet.2023.109458
16. [16]
  Chunmao Yuan , Yanrong Zeng , Lei Huang , Yu Mou , Jun Jin , Ping Yi , Yanmei Li , Xiaojiang Hao . Hymoins A–C, three unusual polycyclic polyprenylated acylphloroglucinols with lipid-lowering activity from Hypericum monogynum. Chinese Chemical Letters, 2025, 36(3): 109859-. doi: 10.1016/j.cclet.2024.109859
17. [17]
  Tingting Huang , Zhuanlong Ding , Hao Liu , Ping-An Chen , Longfeng Zhao , Yuanyuan Hu , Yifan Yao , Kun Yang , Zebing Zeng . Electron-transporting boron-doped polycyclic aromatic hydrocarbons: Facile synthesis and heteroatom doping positions-modulated optoelectronic properties. Chinese Chemical Letters, 2024, 35(4): 109117-. doi: 10.1016/j.cclet.2023.109117
18. [18]
  Wu-Yang Liu , Xin-Xiang Lei , Wen-Ji Wang , Jun-Mian Tian , Yu-Qi Gao , Jin-Ming Gao . Hyperforatone A, the 1,8-seco rearranged polycyclic polyprenylated acylphloroglucinol with a unique bicyclo[5.4.0]undecane core from Hypericum perforatum. Chinese Chemical Letters, 2025, 36(4): 110478-. doi: 10.1016/j.cclet.2024.110478
19. [19]
  Peng Chen , Lijuan Liang , Yufei Zhu , Zhimin Xing , Zhenhua Jia , Teck-Peng Loh . Strategies for constructing seven-membered rings: Applications in natural product synthesis. Chinese Chemical Letters, 2024, 35(6): 109229-. doi: 10.1016/j.cclet.2023.109229
20. [20]
  Yan Luo , Yan-Jiao Lu , Mei-Mei Pan , Yu-Feng Liang , Wei-Min Shi , Chun-Hua Chen , Cui Liang , Gui-Fa Su , Dong-Liang Mo . Rapidly diastereoselective assembly of ten-membered N-heterocycles between two 1,3-dipoles and their diversity to access fused N-heterocycles. Chinese Chemical Letters, 2025, 36(5): 110207-. doi: 10.1016/j.cclet.2024.110207

Get Citation

PDF

XML

Metrics

PDF Downloads(13)
Abstract views(1461)
HTML views(234)

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