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

doi:10.6023/cjoc202005033

Chinese Journal of Organic Chemistry ›› 2020, Vol. 40 ›› Issue (10): 3347-3353.DOI: 10.6023/cjoc202005033 Previous Articles Next Articles

Special Issue: 黄乃正院士七十华诞专辑

利用扩环反应策略向稠环芳烃引入八元环

潘世豪, 缪谦

香港中文大学化学系香港

收稿日期:2020-05-14 修回日期:2020-06-26 发布日期:2020-07-17
通讯作者: 缪谦 E-mail:miaoqian@cuhk.edu.hk
基金资助:
香港研究资助局优配研究金（No.GRF14300919）资助项目.

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

Received:2020-05-14 Revised:2020-06-26 Published:2020-07-17
Supported by:
Project supported by the Research Grants Council of Hong Kong (No. GRF 14300919).

1. cjoc202005033.pdf(2833KB)

Cite this article

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.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

[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] 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.
[3] Barth, W. E.; Lawton, R. G. J. Am. Chem. Soc. 1966, 88, 380.
[4] Luo, J.; Xu, X.; Mao, R.; Miao, Q. J. Am. Chem. Soc. 2012, 134, 13796.
[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] Pun, S. H.; Chan, C. K.; Luo, J.; Liu, Z.; Miao, Q. Angew. Chem., Int. Ed. 2018, 57, 1581.
[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] Mackay, A. L.; Terrones, H. Nature 1991, 352, 762.
[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.
[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.
[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] Christoph, H.; Grunenberg, J.; Hopf, H.; Dix, I.; Jones, P. G.; Scholtissek, M.; Maier, G. Chem. Eur. J. 2008, 14, 5604.
[13] (a) Wong, H. N. C.; Sondheimer, F. Tetrahedron 1981, 37, 99.
(b) Wong, H. N. C. Acc. Chem. Res. 1989, 22, 145.
[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] Cheung, K. Y.; Xu, X.; Miao, Q. J. Am. Chem. Soc. 2015, 137, 3910.
[16] Resendiz, M. J. E.; Garcia-Garibay, M. A. Org. Lett. 2005, 7, 371.
[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] (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] Zhai, L.; Shukla, R.; Rathore, R. Org. Lett. 2009, 11, 3474.
[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] (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] (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] 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.
[24] CCDC2003773 contains the crystallographic data for 9. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre.
[25] Anslyn, E. V.; Dougherty, D. A. Modern Physical Organic Chemistry, University Science Books, Sausalito, 2004, Chapter 1, p. 22.
[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] (a) Wu, J.; Pisula, W.; Müllen, K. Chem. Rev. 2007, 107, 718.
(b) Zhi, L.; Müllen, K. J. Mater. Chem. 2008, 18, 1472.

利用扩环反应策略向稠环芳烃引入八元环

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

PDF

Supporting Info.

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 7

Recommended Articles

Metrics

Comments

[1]	Xiaoting Qin, Ning Zou, Caimei Nong, Dongliang Mo. Recent Advances on the Synthesis of Nine-Membered N-Heterocycles [J]. Chinese Journal of Organic Chemistry, 2023, 43(1): 130-155.
[2]	Wei Wang, Xue Cui, Jianting Ma, Youbin Li, Xuesong Wang. Base-Promoted Ring Expansion Reactions for the Construction of Cycloheptanones through C—C Bond Cleavage [J]. Chinese Journal of Organic Chemistry, 2021, 41(7): 2715-2722.
[3]	Lulu Yu, Qunshan Ding, Chuanjun Song, Junbiao Chang. Enantioselective Total Synthesis of (–)-Angustureine [J]. Chinese Journal of Organic Chemistry, 2021, 41(6): 2507-2510.
[4]	Xinyuan Zhang, Li Lin, Jing Li, Shiyu Duan, Yuhang Long, Jiahong Li. Recent Progress in the Synthesis of Medium-Sized Ring and Macrocyclic Compounds [J]. Chinese Journal of Organic Chemistry, 2021, 41(5): 1878-1887.
[5]	Wenhao Yuan, Jiaxi Xu. Ring Expansions of Oxetanes [J]. Chinese Journal of Organic Chemistry, 2021, 41(3): 947-958.
[6]	Hu Hui, Hu Xiaoping, Chen Ming, Sun Ning, Liu Yuanhong. Gold-Catalyzed Ring Expansion Reaction: Highly Efficient Synthesis of Functionalized 2, 3-Benzodiazepine Scaffolds [J]. Chin. J. Org. Chem., 2018, 38(1): 190-199.
[7]	Liu Wu, Xiao Fenfen, Hu Xiangdong. Concise Synthesis of Lucidone and Methyl Lucidone [J]. Chin. J. Org. Chem., 2013, 33(07): 1587-1590.