[4+4] Photodimerization of Anthracene Derivatives: Recent Synthetic Advances and Applications

doi:10.6023/cjoc20161101

Chin. J. Org. Chem. ›› 2017, Vol. 37 ›› Issue (3): 543-554.DOI: 10.6023/cjoc20161101 Previous Articles Next Articles

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蒽衍生物的光化学[4+4]二聚反应:近期合成进展与应用

刘伟刚^a,b, 郭利峰^a,b, 范洋洋^a,b, 黄泽傲^a,b, 丛欢^a,b

a 中国科学院理化技术研究所光化学转换与功能材料院重点实验室北京 100190;
b 中国科学院大学未来技术学院北京 100190

收稿日期:2016-11-02 修回日期:2016-12-06 发布日期:2016-12-12
通讯作者: 丛欢,E-mail:hcong@mail.ipc.ac.cn;Tel.:86-10-82543492 E-mail:hcong@mail.ipc.ac.cn
基金资助:
中组部“青年千人计划”、国家自然科学基金（No.21672227）、中国科学院（No.XDB17030200）及中国博士后科学基金（No.2016M601140）资助项目.

[4+4] Photodimerization of Anthracene Derivatives: Recent Synthetic Advances and Applications

Liu Weigang^a,b, Guo Lifeng^a,b, Fan Yangyang^a,b, Huang Zeao^a,b, Cong Huan^a,b

a CAS Key Laboratory of Photochemical Conversion and Optoelectronic Materials, Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Beijing 100190;
b School of Future Technology, University of Chinese Academy of Sciences, Beijing 100190

Received:2016-11-02 Revised:2016-12-06 Published:2016-12-12
Contact: 10.6023/cjoc201611001 E-mail:hcong@mail.ipc.ac.cn
Supported by:
Project supported by the "Thousand Youth Talents Plan", the National Natural Science Foundation of China (No. 21672227), the Chinese Academy of Sciences (No. XDB17030200) and the China Postdoctoral Science Foundation (No. 2016M601140).

The[4+4] photodimerizations of anthracene and its derivatives have been extensively studied for over a century. This classic photochemical reaction features broad substrate scope, user-friendly operation, and controllable reversibility. However, the synthetic applications of anthracene photodimerizations have been underdeveloped thus far, largely because of stereoisomer separation and solubility problems of the dianthracene products. Considering that the dianthracene products display unique molecular rigidity and geometry, further studies to improve the synthetic utility of anthracene photodimerizations should be warranted. This review summarizes the representative works of anthracene photodimerizations since the beginning of the 21st century, highlighting the synthetic advances to improve the reaction regio- and enantio-selectivity, as well as the synthetic applications toward functional organic molecules and molecular machines.

Key words: anthracene, photochemistry, dimerization, [4+4] cycloaddition, synthetic applications

Cite this article

Liu Weigang, Guo Lifeng, Fan Yangyang, Huang Zeao, Cong Huan. [4+4] Photodimerization of Anthracene Derivatives: Recent Synthetic Advances and Applications[J]. Chin. J. Org. Chem., 2017, 37(3): 543-554.

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References

[1] Becker, H.-D. Chem. Rev. 1993, 93, 145.
[2] Bouas-Laurent, H.; Castellan, A.; Desvergne,J.-P.; Lapouyade, R. Chem. Soc. Rev. 2000, 29, 43.
[3] Bouas-Laurent, H.; Castellan, A.; Desvergne, J.-P.; Lapouyade, R. Chem. Soc. Rev. 2001, 30, 248.
[4] For selected examples on photodimerizations of heteroaromatics:(a) Zhang, Y.; Wang, L.; Zhang, M.; Fun, H.-K.; Xu, J.-H. Org. Lett. 2004, 6, 4893;
(b) Wang, R.; Yuan, L.; Macartney, D. H. J. Org. Chem. 2006, 71, 1237;
(c) Ihmels, H.; Luo, J. J. Photochem. Photobiol., A 2008, 200, 3.
[5] For selected examples on photodimerizations of naphthalene derivatives:
(a) Tung, C.-H.; Wang, Y.-M. J. Am. Chem. Soc. 1990, 112, 6322.
(b) Lei, L.; Wu, L.-Z.; Wu, X.-L.; Liao, G.-H.; Luo, L.; Zhang, L.-P.; Tung, C.-H.; Ding, K.-L. Tetrahedron Lett. 2006, 47, 4725.
(c) Luo, L.; Cheng, S.-F.; Chen, B.; Tung, C.-H.; Wu, L.-Z; Langmuir 2010, 26, 782.
(d) Xu, H.-X.; Cheng, S.-F.; Yang, X.-J.; Chen, B.; Chen, Y.; Zhang, L.-P.; Wu, L.-Z.; Fang, W.; Tung, C.-H.; Weiss, R. G. J. Org. Chem. 2012, 77, 1685.
[6] For selected examples on photodimerizations of tetracene and pentacene:
(a) Reichwagen, J.; Hopf, H.; Del Guerzo, A.; Desvergne, J.-P.; Bouas-Laurent, H. Org. Lett. 2004, 6, 1899.
(b) Benard, C. P.; 'Geng, Z.; Heuft, M. A.; VanCrey, K.; Fallis, A. G. J. Org. Chem. 2007, 72, 7229.
[7] Takaguchi, Y.; Tajima, T.; Ohta, K.; Motoyoshiya, J.; Aoyama, H. Chem. Lett. 2000, 29, 1388.
[8] Cao, D.; Meier, H. Angew. Chem., Int. Ed. 2001, 40, 186.
[9] Benard, C. P.; Geng, Z.; Heuft, M. A.; VanCrey, K.; Fallis, A. G. J. Org. Chem. 2007, 72, 7229.
[10] Liang, C.-K.; Desvergne, J.-P.; Bassani, D. M. Photochem. Photobiol. Sci. 2014, 13, 316.
[11] Fukuhara, G.; Iida, K.; Kawanami, Y.; Tanaka, H.; Mori, T.; Inoue, Y. J. Am. Chem. Soc. 2015, 137, 15007.
[12] Li, P.; Wong, B. M.; Zakharov, L. N.; Jasti, R. Org. Lett. 2016, 18, 1574.
[13] Tung, C.-H.; Wu, L.-Z.; Zhang, L.-P.; Chen, B. Acc. Chem. Res. 2003, 36, 39.
[14] Schmidt, G. M. J. Pure Appl. Chem. 1971, 27, 647.
[15] Ito, Y.; Fujita, H. J. Org. Chem. 1996, 61, 567.
[16] Ihmels, H.; Leusser, D.; Pfeiffer, M.; Stalke, D. Tetrahedron 2000, 56, 6867.
[17] Horiguchi, M.; Ito, Y. J. Org. Chem. 2006, 71, 3608.
[18] Yamada, S.; Kawamura, C. Org. Lett. 2012, 14, 1572.
[19] Tung, C. H.; Wu, L. Z.; Yuan, Z. Y.; Su, N. J. Am. Chem. Soc. 1998, 120, 11594.
[20] Tung, C.-H., Guang, J.-Q. J. Org. Chem. 1998, 63, 5857.
[21] Wu, D.-Y.; Zhang, L.-P.; Wu, L.-Z.; Wang, B.-J.; Tung, C.-H. Tetrahedron Lett. 2002, 43, 1281.
[22] Wu, D.-Y.; Chen, B.; Fu, X.-G.; Wu, L.-Z.; Zhang, L.-P.; Tung, C.-H. Org. Lett. 2003, 5, 1075.
[23] Gui, J.-C.; Yan, Z.-Q.; Peng, Y.; Yi, J.-G.; Zhou, D.-Y.; Su, D.; Zhong, Z.-H.; Gao, G.-W.; Wu, W.-H.; Yang, C. Chin. Chem. Lett. 2016, 27, 1017.
[24] Marquis, D.; Desvergne, J.-P.; Bouas-Laurent, H. J. Org. Chem. 1995, 60, 7984.
[25] Hiraga, H.; Morozumi, T.; Nakamura, H. Tetrahedron Lett. 2002, 43, 9093.
[26] Rau, H. Chem. Rev. 1983, 83, 535.
[27] Inoue, Y. Chem. Rev. 1992, 92, 741.
[28] Yang, C.; Inoue, Y. Chem. Soc. Rev. 2014, 43, 4123.
[29] Yang, C.; Mori, T.; Origane, Y.; Ko, H. Y.; Selvapalam, N.; Kim, K.; Inoue, Y. J. Am. Chem. Soc. 2008, 130, 8574.
[30] Yang, C.; Ke, C.-F.; Liang, W.; Fukuhara, G.; Mori, T.; Liu, Y.; Inoue, Y. J. Am. Chem. Soc. 2011, 133, 13786.
[31] Yao, J.; Yan, Z.; Ji, J.; Wu, W.; Yang, C.; Nishijima, M.; Fukuhara, G.; Mori, T.; Inoue, Y. J. Am. Chem. Soc. 2014, 136, 6916.
[32] Nishijima, M.; Wada, T.; Mori, T.; Pace, T. C. S.; Bohne, C.; Inoue, Y. J. Am. Chem. Soc. 2007, 129, 3478.
[33] Nishijima, M.; Kato, H.; Fukuhara, G.; Yang, C.; Mori, T.; Maruyama, T.; Otagiri, M.; Inoue, Y. Chem. Commun. 2013, 49, 7433.
[34] Nishijima, M.; Goto, M.; Fujikawa, M.; Yang, C.; Mori, T.; Wada, T.; Inoue, Y. Chem. Commun. 2014, 50, 14082.
[35] Kawanami, Y.; Katsumata, S.-Y.; Nishijima, M.; Fukuhara, G.; Asano, K.; Suzuki, T.; Yang, T.; Nakamura, A.; Mori, T.; Inoue, Y. J. Am. Chem. Soc. 2016, 138, 12187.
[36] Fukuhara, G.; Nakamura, T.; Kawanami, Y.; Yang, C.; Mori, T.; Hiramatsu, H.; Dan-oh, Y.;Tsujimoto, K.; Inoue, Y. Chem. Commun. 2012, 48, 9156.
[37] Fukuhara, G.; Nakamura, T.; Kawanami, Y.; Yang, C.; Mori, T.; Hiramatsu, H.; Dan-oh, Y.; Nishimoto, T.; Tsujimoto, K.; Inoue, Y. J. Org. Chem. 2013, 78, 10996.
[38] Fukuhara, G.; Iida, K.; Kawanami, Y.; Tanaka, H.; Mori, T.; Inoue, Y. J. Am. Chem. Soc. 2015, 137, 15007.
[39] Kohmoto, S.; Ono, Y.; Masu, H.; Yamaguchi, C.; Kishikaw, K.; Yamamoto, M. Org. Lett. 2001, 3, 4153.
[40] Sakamoto, M.; Unosawa, A.; Kobaru, S.; Saito, A.; Mino, T.; Fujita, T. Angew. Chem., Int. Ed. 2005, 44, 5523.
[41] Sakamoto, M.; Unosawa, A.; Kobaru, S.; Hasegawa, Y.; Mino, T.; Kasashima, Y.; Fujita, T.; Chem. Commun. 2007, 1632.
[42] Barth, J. V.; Costantini, G.; Kern, K. Nature 2005, 437, 671.
[43] Kissel, P.; Heijst, J.; Enning, R.; Stemmer, A.; Schlüter, A. D.; Sakamoto, J. Org. Lett. 2010, 12, 2778.
[44] Li, M.; Schlüter, A. D.; Sakamoto, J. J. Am. Chem. Soc. 2012, 134, 11721.
[45] Kissel, P.; Erni, R.; Schweizer, W. B.; Rossell, M. D.; King, B. T.; Bauer, T.; Götzinger, S.; Schlüter, A. D.; Sakamoto, J. Nat. Chem. 2012, 4, 287.
[46] Murray, D. J.; Patterson, D. D.; Payamyar, P.; Bhola, R.; Song, W.; Lackinger, M.; Schlüter, A. D.; King, B. T. J. Am. Chem. Soc. 2015, 137, 3450.
[47] Huang, Z.-A.; Chen, C.; Yang, X.-D.; Fan, X.-B.; Zhou, W.; Tung, C.-H.; Wu, L.-Z.; Cong, H. J. Am. Chem. Soc. 2016, 138, 11144.
[48] Schäfer, C.; Mattay, J. Photochem. Photobiol. Sci. 2004, 3, 331.
[49] Hao, W.; Fang, L.; Helgeson, R. C.; Houk, K. N. Angew. Chem., Int. Ed. 2013, 52, 655.
[50] Molard, Y.; Bassani, D. M.; Desvergne, J.-P.; Horton, P. N.; Hursthouse, M. B.; Tucker, J. H. R. Angew. Chem., Int. Ed. 2005, 44, 1072.
[51] Molard, Y.; Bassani, D. M.; Desvergne, J.-P.; Moran, N.; Tucker, J. H. R. J. Org. Chem. 2006, 71, 8523.
[52] Chih-Kai, L.; Dubacheva, G. V.; Buffeteau, T.; Cavagnat, D.; Hapiot, P.; Fabre, B.; Tucker, J. H. R.; Bassani, D. M. Chem. Eur. J. 2013, 19, 12748.
[53] Hirose, K.; Shiba, Y.; Ishibashi, K.; Doi, Y.; Tobe, Y. Chem. Eur. J. 2008, 14, 3427.
[54] Tron, A.; Thornton, P. J.; Lincheneau, C.; Desvergne, J.-P.; Spencer, N.; Tucker, J. H. R.; McClenaghan, N. D. J. Org. Chem. 2015, 80, 988.
[55] Tron, A.; Jacquot de Rouville, H.-P.; Ducrot, A.;Tucker, J. H. R.; Baroncini, M.; Credi, A.; McClenaghan, N. D. Chem. Commun. 2015, 51, 2810.
[56] Castellano, M.; Ferrando-Soria, J.; Pardo, E.; Julve, M.; Lloret, F.; Mathoniere, C.; Pasan, J.; Ruiz-Perez, C.; Canadillas-Delgado, L.; Ruiz-Garcia, R.; Cano, J. Chem. Commun. 2011, 47, 11035.
[57] Carvalho, C. P.; Dominguez, Z.; Silva, J. P. D.; Pischel, U. Chem. Commun. 2015, 51, 2698.
[58] For selected reviews:
(a) Sieburth, S. M.; Cunard, N. T. Tetrahedron 1996, 52, 6251.
(b) Hoffmann, N. Chem. Rev. 2008, 108, 1052.
(c) Meier, H.; Cao, D. Chem. Soc. Rev. 2013, 42, 143.

蒽衍生物的光化学[4+4]二聚反应:近期合成进展与应用

[4+4] Photodimerization of Anthracene Derivatives: Recent Synthetic Advances and Applications

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