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2020 , Vol. 40 >Issue 11: 3633 - 3645

DOI: https://doi.org/10.6023/cjoc202006081

综述与进展

[60]富勒烯稠合杂环化合物的电化学反应研究进展

  • 牛闯 ,
  • 王官武
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  • 中国科学技术大学化学与材料科学学院 合肥 230026

收稿日期: 2020-06-30

  修回日期: 2020-08-13

  网络出版日期: 2020-08-19

基金资助

国家自然科学基金（No.21572211）资助项目.

收起

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

  • Niu Chuang ,
  • Wang Guanwu
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  • 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).

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摘要

由于富勒烯衍生物在材料科学和生命科学等领域具有潜在的应用价值，化学家们在过去30年来一直致力于其合成，并且报道了众多功能化富勒烯的合成方法.在这些方法中，电化学合成因其反应条件温和、区域选择性良好和产率相对较高等优点，被认为是制备各种富勒烯衍生物的新颖且高效的策略.电化学还原会导致富勒烯衍生物中杂环结构单元在富勒烯骨架上的碳-杂原子键断裂和重排，为富勒烯衍生物的多官能化提供了新的模式，从而使[60]富勒烯稠合杂环化合物的电化学功能化近年来引起了更为广泛的关注.综述了2011年以来[60]富勒烯稠合杂环化合物的电化学反应研究进展.

关键词： [60]富勒烯; [60]富勒烯稠合杂环化合物; 电化学反应; 新加成模式

本文引用格式

牛闯 , 王官武 . [60]富勒烯稠合杂环化合物的电化学反应研究进展[J]. 有机化学, 2020 , 40(11) : 3633 -3645 . DOI: 10.6023/cjoc202006081

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.

Key words： [60]fullerene; [60]fullerene-fused heterocycle; electrochemical reaction; new addition pattern

参考文献

[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.
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