SIOC 中文
CJOG
Adv search

Chinese Journal of Organic Chemistry >

2022 , Vol. 42 >Issue 8: 2390 - 2405

DOI: https://doi.org/10.6023/cjoc202202039

REVIEW

Progress in the Synthesis and Derivatization of Norcorrole

  • Sha Li ,
  • Yahan Sun ,
  • Yankui Meng ,
  • Xiaofang Li ,
  • Shaowei Zhang
Expand
  • Key Laboratory of Theoretical Organic Chemistry and Functional Molecules, Ministry of Education, School of Chemistry and Chemical Engineering, Hunan University of Science and Technology, Xiangtan, Hunan 411201
* E-mail: ;

Received date: 2022-02-28

  Revised date: 2022-04-13

  Online published: 2022-04-29

Supported by

National Natural Science Foundation of China(22171076); Science and Technology Innovation Program of Hunan Province(2021RC5028)

Fold

Abstract

In recent years, norcorrole has attracted extensive attention of scientific researchers, owing to its distinct paratropic ring current, high single molecule conductivity, narrow HOMO-LUMO gap, stable redox performance and unique chemical reactivity. The different synthetic methods of norcorrole in recent years are reviewed, with emphasis on the derivatization reactions in four aspects: insertion, substitution, redox and extension of π conjugated system, and the development of norcorrole is prospected.

Key words： norcorrole; synthesis; derivatization; antiaromaticity

Cite this article

Sha Li , Yahan Sun , Yankui Meng , Xiaofang Li , Shaowei Zhang . Progress in the Synthesis and Derivatization of Norcorrole[J]. Chinese Journal of Organic Chemistry, 2022 , 42(8) : 2390 -2405 . DOI: 10.6023/cjoc202202039

References

[1]
Proft, F. D.; Geerlings, P. Chem. Rev. 2001, 101, 1451.
[2]
Krygowski, T. M.; Cyrański, M. K. Chem. Rev. 2001, 101, 1385.
[3]
Schleyer, P. R.; Manoharan, M.; Wang, Z. X.; Kiran, B.; Jiao, H.; Puchta, R.; Hommes, N. E. Org. Lett. 2001, 3, 2465.
[4]
Liu, J.; Ma, J.; Zhang, K.; Ravat, P.; Machta, P.; Avdoshenko, S.; Hennersdorf, F.; Komber, H.; Pisula, W.; Weigand, J. J.; Popov, A. A.; Berger, R.; Müllen, K.; Feng, X. J. Am. Chem. Soc. 2017, 139, 7513.
[5]
Breslow, R.; Foss, F. W. J. Phys.: Condens. Matter. 2008, 20, 374104.
[6]
Nishinaga, T.; Uto, T.; Inoue, R.; Matsuura, A.; Treitel, N.; Rabinovitz, M.; Komatsu, K. Chem.-Eur. J. 2008, 14, 2067.
[7]
Fan, C.; Mercier, L. G.; Piers, W. E.; Tuononen, H. M.; Parvez, M. J. Am. Chem. Soc. 2010, 132, 9604.
[8]
Breslow, R.; Schneebeli, S. T. Tetrahedron. 2011, 67, 10171.
[9]
Ghosh, A.; Wasbotten, I. H.; Davis, W.; Swarts, J. C. Eur. J. Inorg. Chem. 2005, 22, 4479.
[10]
Sessler, J. L.; Tomat, E. Acc. Chem. Res. 2007, 40, 371.
[11]
Aviv-Harel, I.; Gross, Z. Chem.-Eur. J. 2009, 15, 8382.
[12]
Nozawa, R.; Yamamoto, K.; Shin, J. Y.; Hiroto, S.; Shinokubo, H. Angew. Chem., Int. Ed. 2015, 54, 8454.
[13]
Liu, B.; Yoshida, T.; Li, X.; Stępień, M.; Shinokubo, H.; Chmielewski, P. J. Angew. Chem., Int. Ed. 2016, 55, 13142.
[14]
Tu, X. M.; Xie, Q. J.; Jiang, S. Y.; Yao, S. Z. Biosens. Bioelectron. 2007, 22, 2819.
[15]
Suga, T.; Sugita, S.; Ohshiro, H.; Oyaizu, K.; Nishide. H. Adv. Mater. 2011, 23, 751.
[16]
Shin, J. Y.; Yamada, T.; Yoshikawa, H.; Awaga, K.; Shinokubo, H. Angew. Chem., Int. Ed. 2014, 53, 3096.
[17]
Deng, K.; Li, X.; Huang, H. Electrochim. Acta 2016, 204, 84.
[18]
Fujii, S.; Marqués-González, S.; Shin, J. Y.; Shinokubo, H.; Masuda, T.; Nishino, T.; Arasu, N. P.; Vázquez, H.; Kiguchi, M. Nat. Commun. 2017, 8, 15984.
[19]
Ukai, S.; Koo, Y. H.; Fukui, N.; Seki, S.; Shinokubo, H. Dalton Trans. 2020, 49, 14383.
[20]
Bröring, M.; Köhler, S.; Kleeberg, C. Angew. Chem., Int. Ed. 2008, 47, 5658.
[21]
Ito, T.; Hayashi, Y.; Shimizu, S.; Shin, J. Y.; Kobayashi, N.; Shinokubo, H. Angew. Chem., Int. Ed. 2012, 51, 8542.
[22]
Yoshida, T.; Sakamaki, D.; Seki, S.; Shinokubo, H. Chem. Commun. 2017, 53, 1112.
[23]
Liu, S.; Tanaka, H.; Nozawa, R.; Fukui, N.; Shinokubo, H. Chem.-Eur. J. 2019, 25, 7618.
[24]
Yoshida, T.; Takahashi, K.; Ide, Y.; Kishi, R.; Fujiyoshi, J.; Lee, S.; Hiraoka, Y.; Kim, D.; Nakano, M.; Ikeue, T.; Yamada, H.; Shinokubo, H. Angew. Chem., Int. Ed. 2018, 57, 2209.
[25]
Murakami, K.; Yamamoto, Y.; Yorimitsu, H.; Osuka, A. Chem.-Eur. J. 2013, 19, 9123.
[26]
Yonezawa, T.; Shafie, S. A.; Hiroto, S.; Shinokubo, H. Angew. Chem., Int. Ed. 2017, 56, 11822.
[27]
Zhang, S.; Zhang, D.; Liebeskind, L. S. J. Org. Chem. 1997, 62, 2312.
[28]
Yoshida, T.; Shafie, S. A.; Kawashima, H.; Fukui, N.; Shinokubo, H. Org. Lett. 2021, 23, 2826.
[29]
Kido, H.; Shin, J. Y.; Shinokubo, H. Angew. Chem., Int. Ed. 2013, 52, 13727.
[30]
Kira, M.; Ishida, S.; Iwamoto, T.; Kabuto, C. J. Am. Chem. Soc. 1999, 121, 9722.
[31]
Fukuoka, T.; Uchida, K.; Sung, Y. M.; Shin, J. Y.; Ishida, S.; Lim, J. M.; Hiroto, S.; Furukawa, K.; Kim, D.; Iwamoto, T.; Shinokubo, H. Angew. Chem., Int. Ed. 2014, 53, 1506.
[32]
Liu, S. Y.; Fukuoka, T.; Fukui, N.; Shin, J. Y.; Shinokubo, H. Org. Lett. 2020, 22, 4400.
[33]
Ren, D.; Smaga, O.; Fu, X.; Li, X.; Pawlicki, M.; Koniarz, S.; Chmielewski, P. J. Org. Lett. 2021, 23, 1032.
[34]
Horie, M.; Hayashi, Y.; Yamaguchi, S.; Shinokubo, H. Chem.-Eur. J. 2012, 18, 5919.
[35]
Li, X.; Sun, Y. H.; Yu, X. Y.; Tan, J. X. CN 112174972, 2021.
[36]
Yoshida, T.; Shinokubo, H. Mater. Chem. Front. 2017, 1, 1853.
[37]
Li, X.; Liu, B.; Yi, P.; Yi, R.; Yu, X.; Chmielewski, P. J. J. Org. Chem. 2011, 76, 2345.
[38]
Liu, B.; Li, X.; Zhang, J.; Chmielewski, P. J. Org. Biomol. Chem. 2013, 11, 4831.
[39]
Ren, D.; Fu, X.; Li, X.; Koniarz, S.; Chmielewski, P. J. Org. Chem. Front. 2019, 6, 2924.
[40]
Koley, D.; Colón, O. C.; Savinov, S. N. Org. Lett. 2009, 11, 4172.
[41]
Deng, Z.; Li, X.; Stępień, M.; Chmielewski, P. J. Chem.-Eur. J. 2016, 22, 4231.
[42]
Kawashima, H.; Hiroto, S.; Shinokubo, H. J. Org. Chem. 2017, 82, 10425.
[43]
Li, S.; Smaga, O.; Sun, Y.; Li, X.; Pawlicki, M.; Sukniewiczb, M.; Chmielewski, P. J. Org. Chem. Front. 2021, 8, 3639.
[44]
Shafie, S. A.; Kawashima, H.; Miyake, Y.; Shinokubo, H. ChemPlusChem 2019, 84, 623.
[45]
Liu, B.; Li, X.; Stępień, M.; Chmielewski, P. J. Chem.-Eur. J. 2015, 21, 7790.
[46]
Nozawa, R.; Yamamoto, K.; Hisaki, I.; Shin, J. Y.; Shinokubo, H. Chem. Commun. 2016, 52, 7106.
[47]
Whitlock, H. W.; Hanauer, R.; Oester, M. Y.; Bower, B. K. J. Am. Chem. Soc. 1969, 91, 7485.
[48]
Ukai, S.; Fukui, N.; Ikeue, T.; Shinokubo, H. Chem. Lett. 2022, 51, 590.
[49]
Silva, A. M. G.; Tomé, A. C.; Neves, M. G. P. M. S.; Silva, A. M. S.; Cavaleiro, J. A. S. J. Org. Chem. 2005, 70, 2306.
[50]
Li, X.; Zhuang, J.; Li, Y.; Liu, H.; Wang, S.; Zhu, D. Tetrahedron Lett. 2005, 46, 1555.
[51]
Li, X.; Chmielewski, P. J.; Xiang, J.; Xu, J.; Jiang, L.; Li, Y.; Liu, H.; Zhu, D. J. Org. Chem. 2006, 71, 9739.
[52]
Fu, X.; Meng, Y.; Li, X.; Stępień, M.; Chmielewski, P. J. Chem. Commun. 2018, 54, 2510.
[53]
Yokoi, H.; Wachi, N.; Hiroto, S.; Shinokubo, H. Chem. Commun. 2014, 50, 2715.
[54]
Li, X.; Meng, Y.; Yi, P.; Stępień, M.; Chmielewski, P. J. Angew. Chem., Int. Ed. 2017, 56, 10810.
[55]
Tanaka, T.; Osuka, A. Chem. Soc. Rev. 2015, 44, 943.
[56]
Tanaka, T.; Osuka, A. Chem.-Eur. J. 2018, 24, 17188.
[57]
Liu, S. Y.; Kawashima, H.; Fukui, N.; Shinokubo, H. Chem. Commun. 2020, 56, 6846.
[58]
Nozawa, R.; Tanaka, H.; Cha, W. Y.; Hong, Y.; Hisaki, I.; Shimizu, S.; Shin, J. Y.; Kowalczyk, T.; Irle, S.; Kim, D.; Shinokubo, H. Nat. Commun. 2016, 7, 13620.
[59]
Nozawa, R.; Kim, J.; Oh, J.; Lamping, A.; Wang, Y.; Shimizu, S.; Hisaki, I.; Kowalczyk, T.; Fliegl, H.; Kim, D.; Shinokubo, H. Nat. Commun. 2019, 10, 3576.
[60]
Kawashima, H.; Ukai, S.; Nozawa, R.; Fukui, N.; Fitzsimmons, G.; Kowalczyk, T.; Fliegl, H.; Shinokubo, H. J. Am. Chem. Soc. 2021, 143, 10676.
[61]
Ukai, S.; Takamatsu, A.; Nobuoka, M.; Tsutsui, Y.; Fukui, N.; Ogi, S.; Seki, S.; Yamaguchi, S.; Shinokubo, H. Angew. Chem., Int. Ed. 2022, 61, e202114230.
Options
Outlines

/

〈 〉