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

doi:10.6023/cjoc202006081

Chinese Journal of Organic Chemistry ›› 2020, Vol. 40 ›› Issue (11): 3633-3645.DOI: 10.6023/cjoc202006081 Previous Articles Next Articles

Special Issue: 创刊四十周年专辑

[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

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 发布日期:2020-08-19
通讯作者: 王官武 E-mail:gwang@ustc.edu.cn
基金资助:
国家自然科学基金（No.21572211）资助项目.

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

Niu Chuang, Wang Guanwu

School of Chemistry and Material Science, University of Science and Technology of China, Hefei 230026

Received:2020-06-30 Revised:2020-08-13 Published:2020-08-19
Supported by:
Project supported by the National Natural Science Foundation of China (No. 21572211).

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

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

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[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.

[60]富勒烯稠合杂环化合物的电化学反应研究进展

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

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[1]	Nana Wang, Jingcheng Xu, Haibo Mei, Hiroki Moriwaki, Kunisuke Izawa, Vadim A. Soloshonok, Jianlin Han. Electrochemical Approaches for Preparation of Tailor-Made Amino Acids [J]. Chinese Journal of Organic Chemistry, 2021, 41(8): 3034-3049.
[2]	SHEN XUEMING;HU CHANGMING. Recent advances in electrochemical fluorination [J]. Chin. J. Org. Chem., 1993, 13(2): 122-128.
[3]	CHEN LIBEI;WANG YUTING;HUANG ZAIFU. Synthesis of thiacrown ethers [J]. Chin. J. Org. Chem., 1990, 10(6): 546-549.
[4]	WANG ZHIQIN;ZHOU WENJUAN. Electrochlorination of diphenylsulfide and diphenyloxide with methylene chloride [J]. Chin. J. Org. Chem., 1988, 8(5): 462-465.
[5]	CAO WENJUAN;GE WENZHENG;HUANG WEIYUAN. Studies on electrochemical fluorination 1. Electrochemical fluorination of tripropylamine [J]. Chin. J. Org. Chem., 1987, 7(2): 133-137.
[6]	PING GUOLIANG;LI HUILI. Potentionstat in electro-organic synthesis [J]. Chin. J. Org. Chem., 1983, 3(3): 213-216.