Advances in the Synthetic Methods of Terphenyls

doi:10.6023/cjoc201409007

Abstract

Terphenyl derivatives possess various biological activities, such as immunosuppressants, antioxidants, neuroprotective activity, cytotoxic activity, and antithrombotic activity, and they are also widely used in liquid crystal materials. Significant effort has been devoted to the synthesis of such compounds. Classified into coupling reaction, cycloaddition, dehydrogenation and other methods, this review provides a summary of recently developed methods for the preparation of terphenyls.

Key words: terphenyls, coupling reaction, cycloaddition reaction, synthesis

Cite this article

Shi Wei, Yu Tingting, Cui Dongmei. Advances in the Synthetic Methods of Terphenyls[J]. Chin. J. Org. Chem., 2015, 35(2): 362-372.

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References

[1] Liu, J. K. Chem. Rev. 2006, 106, 2209.
[2] Kamigauchi, T.; Sakazaki, R.; Nagashima, K.; Kawamura, Y.; Yasuda, Y.; Matsushima, K.; Tani, H.; Takahashi, Y.; Ishii, K.; Suzuki, R.; Koizumi, K.; Nakai, H.; Ikenishi, Y.; Terui, Y. J. Antibiot. 1998, 51, 445.
[3] (a) Yun, B. S.; Lee, I. K.; Kim, J. P.; Yoo, I. D. J. Antibiot. 2000, 53, 114.
(b) Quang, D. N.; Hashimoto, T.; Nukada, M.; Yamamoto, I.; Tanaka, M.; Asakawa, Y. Planta Med. 2003, 69, 1063.
[4] Holzapfel, M.; Kilpert, C.; Steglich, W. Liebigs Ann. Chem. 1989, 797.
[5] Stead, P.; Affleck, K.; Sidebottom, P. J.; Taylor, N. L.; Drake, C.; Todd, M.; Jowett, A.; Webb, G. J. Antibiot. 1999, 52, 89.
[6] (a) Miyamae, T.; Hashizume, H.; Ogawa, T.; Okayama, T.; Nukui, E.; Oshima, K.; Morikawa, T.; Hagiwara, M. Arzneim. Forsch.1997, 47, 13.
(b) Hongou, K.; Miyamae, T.; Hashizume, H.; Oshima, K.; Ogawa, T.; Hongou, T.; Morikawa, T.; Hagiwara, M. Arzneim. Forsch.1997, 47, 1104.
[7] Hu, G.; Tang, H.; Xu, S.-Y. Funct. Mater. 1999, 30, 665 (in Chinese). (胡刚, 唐洪, 徐寿颐, 功能材料, 1999, 30, 665.)
[8] Li, W.-Y.; Zhao, D.-M.; Xiong, X.-Q.; Ma, Q.-Q.; Cheng, M.-S., Chin. J. Org. Chem. 2011, 31, 784 (in Chinese). (李文燕, 赵冬梅, 熊绪琼, 马倩倩, 程卯生, 有机化学, 2011, 31, 784.)
[9] (a) Liang, Y.; Li, J.-H. Chin. J. Org. Chem. 2005, 25, 147 (in Chinese). (梁云, 李金恒, 有机化学, 2005, 25, 147.)
(b) Li, Z.-K.; Wu, Z.-Q.; Deng, H.; Zhou, X.-G. Chin. J. Org. Chem. 2013, 33, 760 (in Chinese). (李正凯, 吴之清, 邓杭, 周向葛, 有机化学, 2013, 33, 760.)
[10] Hassan, J.; Hathroubi, C.; Gozzi, C.; Lemaire, M. Tetrahedron 2001, 57, 7845.
[11] Liu, N.; Liu, C.; Jin, Z.-L., Chin. J. Org. Chem. 2012, 32, 860 (in Chinese). (刘宁, 刘春, 金子林, 有机化学, 2012, 32, 860.)
[12] Zhang, Z.; Zhang, G.-X.; Li, S.-H.; Liu, C.-Y.; Bai, X.-F.; Zhao, Y.-L.; Wang, J.-Y. Chem. Adhesion 2014, 36, 132 (in Chinese). (张智, 张广鑫, 李淑辉, 刘传玉, 白雪峰, 赵毅磊, 王洁莹, 化学与黏合, 2014, 36, 132.)
[13] Li, Z. H.; Wong, M. S.; Tao, Y. Tetrahedron 2005, 61, 5277.
[14] Bolligera, J. L.; Frecha, C. M. Adv. Synth. Catal. 2010, 352, 1075.
[15] Liu, H. Y.; Liu, H. L.; Li, R. X.; Chen, H. Tetrahedron Lett. 2014, 55, 415.
[16] Borhade, S. R.; Waghmode, S. B. Beilstein J. Org. Chem. 2011, 7, 310.
[17] Mandali, P. K.; Chand, D. K. Catal. Commun. 2013, 31, 16.
[18] Ali, I.; Siyo, B.; Hassan, Z.; Malik, I.; Ullah, I.; Ali, A.; Nawaz, M.; Iqbal, J.; Patonay, T.; Villinger, A.; Langer, P. J. Fluorine Chem. 2013, 145, 18.
[19] Yajima, A.; Urao, S.; Yoshioka, Y.; Abe, N.; Katsuta, R.; Nukada, T. Tetrahedron Lett. 2013, 54, 4986.
[20] Peters, M.; Trobe, M.; Tan, H.; Kleineweischede, R.; Breinbauer, R. Chem. Eur. J. 2013, 19, 2442.
[21] Wang, D.-P.; Zhang, X.-D.; Liang, Y.; Li, J.-H., Chin. J. Org. Chem. 2006, 26, 19 (in Chinese). (王德平, 张旭东, 梁云, 李金恒, 有机化学, 2006, 26, 19.)
[22] Corsico, E. F.; Rossi, R. A. Synlet 2000, 230.
[23] Li, J. H.; Liang, Y.; Wang, D. P.; Liu, W. J.; Xie, Y. X.; Yin, D. L. J. Org. Chem. 2005, 70, 2832.
[24] (a) Qiu, D.; Meng, H.; Jin, L.; Wang, S.; Tang, S. B.; Wang, X.; Mo, F. Y.; Zhang, Y.; Wang, J. B. Angew. Chem., Int. Ed. 2013, 52, 11581.
(b) Qiu, D.; Wang, S.; Tang, S. B.; Meng, H.; Jin, L.; Mo, F. Y.; Zhang Y.; Wang, J. B. J. Org. Chem. 2014, 79, 1979.
[25] Yoshikai, N.; Matsuda, H.; Nakamura, E. J. Am. Chem. Soc. 2009, 131, 9590.
[26] Jin, Z.; Li, Y. J.; Ma, Y. Q.; Qiu, L. L.; Fang, J. X. Chem. Eur. J. 2012, 18, 446.
[27] (a) Styring, P.; Grindon, C.; Fisher, C. M. Catal. Lett. 2001, 77, 219.
(b) Tsai, F. Y.; Lin, B. N.; Chen, M. J.; Mou, C. Y.; Liu, S. T. Tetrahedron 2007, 63, 4304.
[28] Ju, J. H.; Nam, H.; Jung, H. M.; Lee, S. Tetrahedron Lett. 2006, 47, 8673.
[29] Shi, S. Y.; Zhang, Y. H. J. Org. Chem. 2007, 72, 5927.
[30] Ranu, B. C.; Dey, R.; Chattopadhyay, K. Tetrahedron Lett. 2008, 9, 3430.
[31] Shao, Z.-Q.; Li, X.; Chang, H.-H.; Wei, W.-L. Chem. Online 2013, 76, 704 (in Chinese). (邵忠奇, 李兴, 常宏宏, 魏文珑, 化学通报, 2013, 76, 704.)
[32] Dai, C. Y.; Fu, G. C. J. Am. Chem. Soc. 2001, 123, 2719.
[33] Xi, Z. X.; Zhou, Y. B.; Chen, W. Z. J. Org. Chem. 2008, 73, 8497.
[34] Liu, N.; Wang, L.; Wang, Z. X. Chem. Commun. 2011, 47, 1598.
[35] Hussain, I.; Singh, T. Adv. Synth. Catal. 2014, 356, 1661.
[36] (a) Hong, W. K.; Qiu, Y. T.; Yao, Z. Y.; Wang, Z. Y.; Jiang, S. Tetrahedron Lett. 2011, 52, 4916.
(b) Liu, W.; Cao, H.; Lei, A. Angew. Chem., Int. Ed. 2010, 49, 2004.
(c) Liu, W.; Cao, H.; Xin, J.; Jin, L. Q.; Lei, A. Chem. Eur. J. 2011, 17, 3588.
[37] Zhao, H. Q.; Shen, J.; Guo, J. J.; Ye, R. J.; Zeng, H. Q. Chem. Commun. 2013, 49, 2323.
[38] Shirakawa, E.; Itoh, K.; Higashino, T.; Hayashi, T. J. Am. Chem. Soc. 2010, 132, 15537.
[39] Dewanji, A.; Murarka, S.; Curran, D. P.; Studer, A. Org. Lett. 2013, 15, 6102.
[40] Li, H. Y.; Wu, Y. Z.; Xu, X. G. J. Inorg. Organomet. Polym. 2011, 21, 827.
[41] Jasti, R.; Bhattacharjee, J.; Neaton, J. B.; Bertozzi, C. R. J. Am. Chem. Soc. 2008, 130, 17646.
[42] Lewis, F. D.; Kurth, T. L.; Hattan, C. M.; Reiter, R. C.; Stevenson, C. D. Org. Lett. 2004, 6, 1605.
[43] (a) Chopade, P. R.; Louie, J. Adv. Synth. Catal. 2006, 348, 2307.
(b) Yang, J. S.; Huang, H. H.; Lin, S. H. J. Org. Chem. 2009, 74, 3974.
(c) Gandon, V.; Aubert, C.; Malacria, M. Chem. Commun. 2006, 2209.
(d) Kotha, S.; Brahmachary, E.; Lahiri, K. Eur. J. Org. Chem. 2005, 4741.
(e) Varela, J. A.; Saa, C. Chem. Rev. 2003, 103, 3787.
(f) Rubin, S. G.; Varela, J. A.; Castedo, L.; Saa, C. Chem. Eur. J. 2008, 14, 9772.
(g) Dominguez, G.; Castells, J. P. Chem. Soc. Rev. 2011, 40, 3430.
[44] (a) Shibata, T.; Fujimoto, T.; Yokota, K.; Takagi, K. J. Am. Chem. Soc. 2004, 126, 8382.
(b) Takechi, R.; Nakaya, Y. Org. Lett. 2003, 5, 3659.
[45] (a) McDonald, F. E.; Smolentsev, V. Org. Lett. 2002, 4, 745.
(b) Tanaka, K.; Shirasaka, K. Org. Lett. 2003, 5, 4697.
(c) Tanaka, K.; Hara, H.; Nishida, G.; Hirano, M. Org. Lett. 2007, 9, 1907.
[46] (a) Deaton, K. R.; Gin, M. S. Org. Lett. 2003, 5, 2477.
(b) Bennett, M. A.; Wenger, E. Organometallics 1996, 15, 5536.
[47] Yamamoto, Y.; Arakawa, T.; Ogawa, R.; Itoh, K. J. Am. Chem. Soc. 2003, 125, 12143.
[48] (a) Gevorgyan, V.; Radhakrishnan, U.; Takeda, A.; Rubina, M.; Rubin, M.; Yamamoto, Y. J. Org. Chem. 2001, 66, 2835.
(b) Davisa, M. C.; Guenthner, A. J.; Sahagun, C. M.; Lamison, K. R.; Reams, J. T.; Mabry, J. M. Polymer 2013, 54, 6902.
[49] (a) Tsuji, H.; Yamagata, K.; Fujimoto, T.; Nakamura, E. J. Am. Chem. Soc. 2008, 130, 7792.
(b) Yoshikai, N.; Zhang, S. L.; Yamagata, K.; Tsuji, H.; Nakamura, E. J. Am. Chem. Soc. 2009, 131, 4099.
[50] Ozerov, O. V.; Ladipo, F. T.; Patrick, B. O. J. Am. Chem. Soc. 1999, 121, 7941.
[51] Wang, C.-X.; Li, X.-C.; Xu, F.; Wan, B.-S. Prog. Chem. 2010, 22, 610 (in Chinese). (王春翔, 李新成, 徐粉, 万伯顺, 化学进展, 2010, 22, 610.)
[52] Murakami, M.; Ubukata, M.; Itami, K.; Ito, Y. Angew. Chem., Int. Ed. 1998, 37, 2248.
[53] Ho, J. H.; Lin, Y. C.; Chou, L. T.; Chen, Y. N.; Liu, W. Q.; Chuang, C. L. Tetrahedron Lett. 2013, 54, 1991.
[54] Asao, N.; Aikawa, H. J. Org. Chem. 2006, 71, 5249.
[55] Zhang, L.; Liang, F. S.; Cheng, X.; Liu, Q. J. Org. Chem. 2009, 74, 899.
[56] Chang, M. Y.; Chan, C. K.; Lin, S. Y.; Wu, M. H. Tetrahedron 2013, 69, 9616.
[57] Petrova, O. V.; Mikhaleva, A. I.; Sobenina, L. N.; Trofimov, B. A. Russ. J. Org. Chem. 2010, 46, 452.
[58] Lim, C. H.; Kim, S. H.; Kim, K. H.; Kim, J. N. Tetrahedron Lett. 2013, 54, 2476.
[59] Jiang, M.; Liu, L. P.; Shi, M.; Li, Y. X. Org. Lett. 2010, 12, 116.
[60] Woods, G. F.; Oppelt, J. C.; Isaacson, R. B. J. Am. Chem. Soc. 1960, 82, 5232.
[61] Callot, H. J.; Chevrier, B.; Weiss, R. J. Am. Chem. Soc. 1979, 101, 7730.
[62] Ames, G. R.; Davey, W. J. Chem. Soc. 1957, 3480.
[63] Hoogesteger, F. J.; Havenith, R. W. A.; Zwikker, J. W. J. Org. Chem. 1995, 60, 4375.
[64] Ikeda, H.; Minegishi, T.; Miyash, T. J. Chem. Soc. 1994, 297.
[65] Adam, W.; Grabowski, S.; Miranda, M. A.; Rubenacker, M. J. Chem. Soc. 1988, 142.
[66] Fieser, L. F.; Haddadin, M. J. J. Am. Chem. Soc. 1964, 86, 2392.
[67] Ajaz, A.; McLaughlin, E. C.; Skraba, S. L.; Thamatam, R.; Johnson, R. P. J. Org. Chem. 2012, 77, 9487.

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