Progress in Electrochemical Reactions of[60]Fullerene-Fused Heterocycles

  • Niu Chuang ,
  • Wang Guanwu
Expand
  • School of Chemistry and Material Science, University of Science and Technology of China, Hefei 230026

Received date: 2020-06-30

  Revised date: 2020-08-13

  Online published: 2020-08-19

Supported by

Project supported by the National Natural Science Foundation of China (No. 21572211).

Abstract

Due to the potential applications of fullerene derivatives in materials science and biological science, chemists have been devoted to their synthesis over the past 30 years, and have reported a great diversity of synthetic protocols to fun-ctionalize fullerenes. Among the numerous methods, electrochemical synthesis has been considered to be a novel and efficient strategy due to its mild reaction conditions, good regioselectivity and relatively high yield. The electrochemical functionalizations of [60]fullerene-fused heterocycles have recently attracted wide interest, because electroreduction results in the carbon-heteroatom bond breaking and rearrangement of the heterocyclic moieties on the fullerene skeleton, consequently providing new addition patterns of fullerene derivatives. The electrochemical reactions of [60]fullerene-fused heterocycles since 2011 are reviewed.

Cite this article

Niu Chuang , Wang Guanwu . Progress in Electrochemical Reactions of[60]Fullerene-Fused Heterocycles[J]. Chinese Journal of Organic Chemistry, 2020 , 40(11) : 3633 -3645 . DOI: 10.6023/cjoc202006081

References

[1] Osawa, E. Kagaku (Kyoto) 1970, 25, 854.
[2] Kroto, H. W.; Heath, J. R.; O'brien, S. O.; Curl, R. F.; Smalley, R. E. Nature 1985, 318, 162.
[3] Krätschmer, W.; Lamb, L. D.; Fostiropoulos, K.; Huffman, D. R. Nature 1990, 347, 354.
[4] Ceulemans, A.; Fowler, P. W. Nature 1991, 353, 52.
[5] Liu, S.; Lu, Y. J.; Kappes, M. M.; Ibers, J. A. Science 1991, 254, 408.
[6] For selected reviews, see:(a) Murata, M.; Murata, Y.; Komatsu, K. Chem. Commun. 2008, 6083.
(b) Vougioukalakis, G. C.; Roubelakis, M. M.; Orfanopoulos, M. Chem. Soc. Rev. 2010, 39, 817.
(c) Itami, K.; Chem. Rec. 2011, 11, 226.
(d) Wang, G.-W.; Li, F.-B. Curr. Org. Chem. 2012, 16, 1109.
(e) Maroto, E. E.; Izquierdo, M.; Reboredo, S.; Marco-Martínez, J.; Filippone, S.; Martín, N. Acc. Chem. Res. 2014, 47, 2660.
(f) Gan, L. Chin. J. Chem. 2018, 36, 991.
(g) Lin, H.-S.; Matsuo, Y. Chem. Commun. 2018, 54, 11244.
[7] For selected reviews, see:(a) Nakamura, E.; Isobe, H. Acc. Chem. Res. 2003, 36, 807.
(b) Giacalone, F.; Martín, N. Chem. Rev. 2006, 106, 5136.
(c) Thompson, B. C.; Fréchet, J. M. J. Angew. Chem., Int. Ed. 2008, 47, 58.
(d) Guldi, D. M.; Illescas, B. M.; Atienza, C. M.; Wielopolski, M.; Martín, N. Chem. Soc. Rev. 2009, 38, 1587.
(e) Balch, A. L.; Winkler, K. Chem. Rev. 2016, 116, 3812.
(f) Illescas, B. M.; Rojo, J.; Delgado, R.; Martín, N. J. Am. Chem. Soc. 2017, 139, 6018.
(g) Wang, Y.; Zheng, L.; Li, J.; Liu, C.; Yao, J. Chin. J. Org. Chem. 2018, 38, 3143(in Chinese). (王宇飞, 郑丽萍, 李靖靖, 刘超, 姚建华, 有机化学, 2018, 38, 3143.)
(h) Umeyama, T.; Imahori, H. Acc. Chem. Res. 2019, 52, 2046. For recent examples, see:
(i) Sun, Y.; Gao, H.; Zhang, Y.; Wang, Y.; Kan, B.;Wan, X.; Zhang, H.; Chen, Y. Chin. J. Org. Chem. 2018, 38, 228(in Chinese). (孙延娜, 高欢欢, 张雅敏, 王云闯, 阚斌, 万相见, 张洪涛, 陈永胜, 有机化学, 2018, 38, 228.)
(j) Li, W.; Yan, D.; Liu, F.; Russell, T.; Zhan C.; Yao, J. Sci. China:Chem. 2018, 61, 1609.
(k) Sun, W.; Ye, L.; Liu, J.; Zheng, L.; Guo, W.; Han, S.; Shao, C.; Jiang, H. Chin. J. Org. Chem. 2019, 39, 2867(in Chinese). (孙卫东, 叶琳, 刘佳, 郑璐, 郭文彩, 韩森凯, 邵成园, 江华, 有机化学, 2019, 39, 2867.)
[8] (a) Haddon, R. C. Acc. Chem. Res. 1992, 25, 127.
(b) Johnson, R. D.; Bethune, D. S.; Yannoni, C. S. Acc. Chem. Res. 1992, 25, 169.
[9] Haddon, R. C.; Brus, L. E.; Raghavachari, K. Chem. Phys. Lett. 1986, 131, 165.
[10] Echegoyen, L.; Echegoyen, L. E. Acc. Chem. Res. 1998, 31, 593.
[11] Nakamura, Y.; O-kawa, K.; Nishimura, J. Bull. Chem. Soc. Jpn. 2003, 76, 865.
[12] Hirsch, A.; Brettreich, M. Fullerenes:Chemistry and Reactions, Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, 2005.
[13] (a) Jensen, A. W.; Khong, A.; Saunders, M.; Wilson, S. R.; Schuster, D. I. J. Am. Chem. Soc. 1997, 119, 7303.
(b) Yamada, M.; Schweizer, W. B.; Schoenebeck, F.; Diederich, F. Chem. Commun. 2010, 46, 5334.
(c) He, C.-L.; Liu, R.; Li, D.-D.; Zhu, S.-E.; Wang, G.-W. Org. Lett. 2013, 15, 1532.
(d) Chen, M.; Bao, L.; Peng, P.; Zheng, S.; Xie, Y.; Lu, X. Angew. Chem., Int. Ed. 2016, 55, 11887.
(e) Jiang, S.-P.; Zhang, M.; Wang, C.-Y.; Yang, S.; Wang, G.-W. Org. Lett. 2017, 19, 5110.
[14] (a) Yang, W.-W.; Li, Z.-J.; Li, F.-F.; Gao, X. J. Org. Chem. 2011, 76, 1384.
(b) Xiao Y.; Wang, G. Chin. J. Chem. 2014, 32, 699.
(c) Majid, H.; Niu, C.; Wang, G.-W. Org. Chem. Front. 2020, 7, 1249.
[15] (a) Schick, G.; Kampe, K.-D.; Hirsch, A. J. Chem. Soc., Chem. Commun. 1995, 2023.
(b) Murata, Y.; Shiro, M.; Komatsu, K. J. Am. Chem. Soc. 1997, 119, 8117.
(c) Deng, L.-L.; Xie, S.-L.; Yuan, C.; Liu, R.-F.; Feng, J.; Sun, L.-C.; Lu, X.; Xie, S.-Y.; Huang, R.-B.; Zheng, L.-S. Sol. Energy Mater. Sol. Cells 2013, 111, 193.
(d) Clikeman, T. T.; Deng, S. H. M.; Avdoshenko, S.; Wang, X.-B.; Popov, A. A.; Strauss, S. H.; Boltalina, O. V. Chem.-Eur. J. 2013, 19, 15404.
[16] (a) Kadish, K. M.; Gao, X.; Caemelbecke, E. V.; Suenobu, T.; Fukuzumi, S. J. Am. Chem. Soc. 2000, 122, 563.
(b) Matsuo, Y.; Iwashita, A.; Abe, Y.; Li, C.-Z.; Matsuo, K.; Hashiguchi, M.; Nakamura, E. J. Am. Chem. Soc. 2008, 130, 15429.
(c) Nambo, M.; Wakamiya, A.; Yamaguchi, S.; Itami, K. J. Am. Chem. Soc. 2009, 131, 15112.
(d) Kuvychko, I. V.; Streletskii, A. V.; Shustova, N. B.; Seppelt, K.; Drewello, T.; Popov, A. A.; Strauss, S. H.; Boltalina, O. V. J. Am. Chem. Soc. 2010, 132, 6443.
(e) Chang, W.-W.; Li, Z.-J.; Yang, W.-W.; Gao, X. Org. Lett. 2012, 14, 2386.
[17] Rubin, Y.; Ganapathi, P. S.; Franz, A.; An, Y.-Z.; Qian, W.; Neier, R. Chem.-Eur. J. 1999, 5, 3162.
[18] (a) Xiao, Y.; Zhu, S.-E.; Liu, D.-J.; Suzuki, M.; Lu, X.; Wang, G.-W. Angew. Chem., Int. Ed. 2014, 53, 3006.
(b) Hou, H.-L.; Li, Z.-J.; Gao, X. Org. Lett. 2014, 16, 712.
(c) Li, Z.-J.; Li, S.-H.; Sun, T.; Hou, H.-L.; Gao, X. J. Org. Chem. 2015, 80, 3566.
(d) Lin, H.-S.; Matsuo, Y.; Wang, J.-J.; Wang, G.-W. Org. Chem. Front. 2017, 4, 603.
(e) Li, F.; Wang, J.-J.; Wang, G.-W. Chem. Commun. 2017, 53, 1852.
[19] (a) Liu, K.-Q.; Wang, J.-J.; Yan, X.-X.; Niu, C.; Wang, G.-W. Chem. Sci. 2020, 11, 384.
(b) Yan, X.-X.; Li, B.; Lin, H.-S.; Jin, F.; Niu, C.; Liu, K.-Q.; Wang, G.-W.; Yang, S. Research 2020, 2020, 2059190.
[20] (a) Hsu, H.-F.; Shapley, J. R. J. Am. Chem. Soc. 1996, 118, 9192.
(b) Tajima, Y.; Takeuchi, K. J. Org. Chem. 2002, 67, 1696.
(c) Chuang, S.-C.; Clemente, F. R.; Khan, S. I.; Houk, K. N.; Rubin, Y. Org. Lett. 2006, 8, 4525.
[21] (a) Birkett, P. R.; Hitchcock, P. B.; Kroto, H. W.; Taylor, R.; Walton, D. R. M. Nature 1992, 357, 479.
(b) Gan, L.; Huang, S.; Zhang, X.; Zhang, A.; Cheng, B.; Cheng, H.; Li, X.; Shang, G. J. Am. Chem. Soc. 2002, 124, 13384.
[22] Hou, H.-L.; Li, Z.-J.; Wang, Y.; Gao, X. J. Org. Chem. 2014, 79, 8865.
[23] Majid, H.; Chen, M.; Yang, S.; Wang, G.-W. Org. Lett. 2019, 21, 8568.
[24] Chen, S.; Li, Z.-J.; Li, S.-H.; Gao, X. Org. Lett. 2015, 17, 5192.
[25] Yang, Y.; Niu, C.; Chen, M.; Yang, S.; Wang, G.-W. Org. Biomol. Chem. 2020, 18, 4783.
[26] Liu, R.; Li, F.; Xiao, Y.; Li, D.-D.; He, C.-L.; Yang, W.-W.; Gao, X.; Wang, G.-W. J. Org. Chem. 2013, 78, 7093.
[27] Wang, J.-J.; Lin, H.-S.; Niu, C.; Wang, G.-W. Org. Biomol. Chem. 2017, 15, 3248.
[28] Niu, C.; Zhou, D.-B.; Yang, Y.; Yin, Z.-C.; Wang, G.-W. Chem. Sci. 2019, 10, 3012.
[29] Niu, C.; Li, B.; Yin, Z.-C.; Yang S.; Wang, G.-W. Org. Lett. 2019, 21, 7346.
Outlines

/