Chinese Journal of Organic Chemistry >
Base-Promoted Ring Expansion Reactions for the Construction of Cycloheptanones through C—C Bond Cleavage
Received date: 2021-01-18
Revised date: 2021-04-08
Online published: 2021-04-25
Supported by
Hainan Provincial Natural Science Youth Foundation of China(820QN264); High-level Talents Fund of Basic and Applied Basic Research Program (Natural Science) of Hainan Province in 2019(2019RC214); Talent Introduction Start-up Fund of Hainan Medical University(XRC180009)
An efficient ring expansion strategy has been developed for the construction of cycloheptanones through C—C bond cleavage. The reactions take place with easily accessible starting materials, good functional group tolerance, and mild reaction conditions in the presence of Cs2CO3 without any metal or oxidant reagent. The transition-metal free insertions of alkynes into carbon-carbon σ-bonds of acenaphthenone initialized through intramolecular nucleophilic addition/ring-opening to furnish multifarious cycloheptanones, which has the potential to be widely utilized in organic synthetic chemistry.
Key words： C—C bond cleavage; ring expansion; base-promoted; cycloheptanone compounds
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 . DOI: 10.6023/cjoc202101031
| [1] | For selected reviews on C—C bond cleavage, see: (a) Chen,P. -H.; Billett,B. A.; Tsukamoto, T.; Dong,, G. ACS Catal. 2017, 7,1340. |
| [1] | (b) Wang, T.; Jiao, N. Acc. Chem. Res. 2014, 47,1137. |
| [1] | (c) Murakami, M.; Matsuda, T. Chem. Commun. 2011, 47,1100. |
| [1] | (d) Jun,C. H. Chem. Soc. Rev. 2004, 33,610. |
| [2] | For selected reviews, see: (a) Souillart, L.; Cramer,, N. Chem. Rev. 2015, 115,9410. |
| [2] | (b) Dermenci, A.; Coe,J. W.; Dong, G. Org. Chem. Front. 2014, 1,567. |
| [2] | (c) Mack,D. J.; Njardarson,J. T. ACS Catal. 2013, 3,272. |
| [2] | (d) Murakami, M.; Amii, H.; Ito, Y. Nature 1994, 370,540. |
| [3] | For selected examples, see: (e) Zhang, H.; Wu,, G.; Yi,, H.; Sun,, T.; Wang,, B.; Zhang,, y.; Dong,, G.; Wang,, J. Angew. Chem. Int. Ed. 2017, 56,3945. |
| [3] | (f) Banik,S. M.; Mennie,,K. M..; Jacobsen,,E. N. J. Am. Chem. Soc. 2017, 139,9152. |
| [3] | (g) Zhao, B.; Shi,, Z. Angew. Chem. Int. Ed. 2017, 56,12727. |
| [4] | (a) Yamamoto,S. -I.; Okamoto, K.; Murakoso, M.; Kuninobu, Y.; Takai, K. Org. Lett. 2012, 14,3182. |
| [4] | (b) Kuninobu, Y.; Matsuzaki, H.; Nishi, M.; Takai, K. Org. Lett. 2011, 13,2959. |
| [4] | (c) Kuninobu, Y.; Takata, H.; Kawata, A.; Takai, K. Org. Lett. 2008, 10,3133. |
| [4] | (d) Kuninobu, Y.; Kawata, A.; Takai, K. J. Am. Chem. Soc. 2006, 128,11368. |
| [4] | (e) Hirata, Y.; Yada, A.; Morita, E.; Nakao, Y.; Hiyama, T.; Ohashi, M.; Ogoshi, S. J. Am. Chem. Soc. 2010, 132,10070. |
| [4] | (f) Hirata, Y.; Inui, T.; Nakao, Y.; Hiyama, T. J. Am. Chem. Soc. 2009, 131,6624. |
| [4] | (g) Nishihara, Y.; Inoue, Y.; Itazaki, M.; Takagi, K. Org. Lett. 2005, 7,2639. |
| [4] | (h) Miura, T.; Shimada, M.; Murakami, M. Angew. Chem. Int. Ed. 2005, 44,7598. |
| [4] | (i) Zhao, J.; Liu, J.; Xie, X.; Li, S.; Liu, Y. Org. Lett. 2015, 17,5926. |
| [5] | (a) Yu,X. -Y.; Chen,J. -R.; Xiao,W. -J. Chem. Rev. 2021, 121,506. |
| [5] | (b) Pirenne, V.; Muriel, B.; Waser, J. Chem. Rev. 2021, 121,227. |
| [5] | (c) Vicente, R. Chem. Rev. 2021, 121,162. |
| [5] | (d) Lu, H.; Yu,T. -Y.; Xu,P. -F.; Wei, H. Chem. Rev. 2021, 121,365. |
| [5] | (e) Nogi, K.; Yorimitsu, H. Chem. Rev. 2021, 121,345. |
| [5] | (f) Cohen, Y.; Cohen, A.; Marek, I. Chem. Rev. 2021, 121,140. |
| [5] | (g) Murakami, M.; Ishida, N. Chem. Rev. 2021, 121,264. |
| [5] | (h) Souillart, L.; Cramer, N. Chem. Rev. 2015, 115,9410. |
| [5] | (i) Lutz,M. D.R.; Morandi, B. Chem. Rev. 2021, 121,300. |
| [5] | (j) Wang, J.; Li, F.; Yu, X.; Liu, L.; Ding, J.; Xie, P.; Wang, J. Chin. J. Org. Chem. 2018, 38,1638 (in Chinese). |
| [5] | ( 王晶晶, 李峰, 于晓波, 刘澜涛, 丁俊汝, 谢佩瑶, 王建辉, 有机化学, 2018, 38,1638.) |
| [5] | (k) Kou, X.; Fan, J.; Tong, X.; Shen, Z. Chin. J. Org. Chem. 2013, 33,1407 (in Chinese). |
| [5] | ( 寇学振, 范佳骏, 童晓峰, 沈增明, 有机化学, 2013, 33,1407.) |
| [5] | (l) Dai, H.; Wu, F.; Bai, D. Chin. J. Org. Chem. 2020, 40,1423 (in Chinese). |
| [5] | ( 代洪雪, 吴芬, 白大昌, 有机化学, 2020, 40,1423.) |
| [6] | (a) Tambar,U. K.; Stoltz,B. M. J. Am. Chem. Soc. 2005, 127,5340. |
| [6] | (b) Yoshida, H.; Shirakawa, E.; Honda, Y.; Hiyama, T. Angew. Chem. Int. Ed. 2002, 41,3247. |
| [6] | (c) Yoshida, H.; Watanabe, M.; Ohshita, J.; Kunai, A. Chem. Commun. 2005,3292. |
| [6] | (d) Yoshida, H.; Watanabe, M.; Morishita, T.; Ohshita, J.; Kunai, A. Chem. Commun. 2007,1505. |
| [6] | (e) Yoshida, H.; Kishida, T.; Watanabe, M.; Ohshita, J. Chem. Commun. 2008,5963. |
| [6] | (f) Li, R.; Tang, H.; Fu, H.; Ren, H.; Wang, X.; Wu, C.; Wu, C.; Shi, F. J. Org. Chem. 2014, 79,1344. |
| [6] | (g) Okuma, K.; Itoyama, R.; Sou, A.; Nagahora, N.; Shioj, K. Chem. Commun. 2012, 48,11145. |
| [6] | (h) Ziadi, A.; Martin, R. Org. Lett. 2012, 14,1266. |
| [6] | (i) Masarwa, A.; Weber, M.; Sarpong, R. J. Am. Chem. Soc. 2015, 137,6327. |
| [6] | (j) Xia, Y.; Liu, Z.; Liu, Z.; Ge, R.; Ye, F.; Hossain, M.; Zhang, Y.; Wang, J. J. Am. Chem. Soc. 2014, 136,3013. |
| [6] | (k) Souillart, L.; Cramer, N. Chem. Sci. 2014, 5,837. |
| [6] | (l) JuliaHernandez, F.; Ziadi, A.; Nishimura, A.; Martin, R. Angew. Chem. Int. Ed. 2015, 54,9537. |
| [6] | (m) Wright,A. C.; Haley,C. K.; Lapointe, G.; Stoltz,B. M. Org. Lett. 2016, 18,2793. |
| [6] | (n) Samineni, R.; Srihari, P.; Mehta, G. Org. Lett. 2016, 18,2832. |
| [7] | Gampe,C. M.; Boulos, S.; Carreira,E. M. Angew. Chem. Int. Ed. 2010, 49,4092. |
| [8] | Yao, Q.; Kong, L.; Wang, M.; Yuan, Y.; Sun, R.; Li, Y. Org. Lett. 2018, 20,1744. |
| [9] | Wang, M.; Yang, Y.; Song, B.; Yin, L.; Yan, S.; Li, Y. Org. Lett. 2020, 22,155. |
| [10] | Yao, Q.; Kong, L.; Zhang, F.; Tao, X.; Li, Y. Adv. Synth. Catal. 2017, 359,3079. |
| [11] | Zhang, F.; Yao, Q.; Yuan, Y.; Xu, M.; Kong, L.; Li, Y. Org. Biomol. Chem. 2017, 15,2497. |
| [12] | (a) Cheng, X.; Zhou, Y.; Zhang, F.; Zhu, K.; Liu, Y.; Li, Y. Chem.-Eur. J. 2016, 22,12655. |
| [12] | (b) Zhou, Y.; Tao, X.; Yao, Q.; Zhao, Y.; Li, Y. Chem.-Eur. J. 2016, 22,17936. |
| [13] | (a) Gill, M.; Steglich, W. Prog. Chem. Org. Nat. Prod. 1987, 51,1. |
| [13] | (b) Hafeman,N. J.; Loskot,S. A.; Reimann,C. E.; Pritchett,B. P.; Virgil,S. C.; Stoltz,B. M. J. Am. Chem. Soc. 2020, 142,8585. |
| [13] | (c) Zhang,P. P.; Yan,Z. M.; Li,Y. H.; Gong,J. X.; Yang, Z. J. Am. Chem. Soc. 2017, 139,13989. |
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