有机催化芳香化反应的研究进展

doi:10.6023/cjoc202001011

摘要/Abstract

芳香族化合物是一类具有特殊香味的化合物，其结构广泛存在于天然产物和药物分子中.在众多小分子药物结构中以苯环结构最为常见.因此，探究构建芳香结构化合物的方法也受到极大的关注并取得了重要的突破，其中以金属催化非环状炔烃或烯烃的环合为主.近年来，有机催化在构筑苯环及其衍生物的过程中得到充分应用.与金属催化相比，有机催化合成含苯环结构化合物的反应可以避免在苯环上引入定位基团或导向基团的步骤，且具有良好的底物适用性.同时，有机催化反应具有高效、操作简便、反应条件温和及原子经济性等优点，引起了合成化学工作者的广泛关注.综述了多类有机小分子催化的非环状前体化合物环化合成多取代苯环结构的反应特点和研究进展.

关键词: 有机催化, 芳香化, 成环反应, 研究进展

Aromatic compounds possess a particular fragrance and are widely present in natural products and pharmaceuticals. Among them, benzenes are the most abundant substructures of commercially available small-molecule drugs. Therefore, a variety of synthetic methodologies for the construction of aromatic compounds have been pursued vigorously and some significant progresses have been achieved. The dominant methods are transition metal-catalyzed benzannulation of enynes with alkynes to construct the functionalized benzenes. The synthesis of substituted benzene derivatives receives constant attentions since the formation and development of organocatalysis. Compared to metal catalysis, the organocatalytic benzannulation reaction avoids the introduction of a direct group into the pre-existed arene ring and appears to be tolerant of a broad range of substrates. While organocatalysis has emerged as a promising green and effieient synthetic tool and attracted a great deal of attention from synthetic chemists. The development of organocatalyzed aromatization reactions from acyclic starting materials is featured.

Key words: organocatalysis, aromatization, annulation, research progress

引用此文

贾乾发, 李娅琼, 林银河. 有机催化芳香化反应的研究进展[J]. 有机化学, 2020, 40(6): 1502-1513.

Jia Qianfa, Li Yaqiong, Lin Yinhe. Recent Advances in Organocatalyzed Aromatization Reactions[J]. Chinese Journal of Organic Chemistry, 2020, 40(6): 1502-1513.

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参考文献

[1] (a) McGrath, N. A.; Brichacek, M.; Njardarson, J. T. J. Chem. Educ. 2010, 87, 1348.
(b) Baumann, M.; Baxendale, I. R.; Ley, S. V.; Nikbin, N. Beilstein J. Org. Chem. 2011, 7, 442.
[2] Davis, R.; Markham, A.; Balfour, J. A. Drugs 1996, 51, 1019.
[3] (a) O'Brien, W. M.; Bagby, G. F. Pharmacotherapy 1987, 7, 16.
(b) Ricketts, A. P.; Lundy, K. M.; Seibel, S. B. Am. J. Vet. Res. 1998, 59, 1441.
(c) Thau-Zuchman, O.; Shohami, E.; Alexandrovich, A. G.; Trembovler, V.; Leker, R. R. J. Neurotraum. 2012, 29, 375.
[4] (a) Chen, Y.; Yekta, S.; Yudin, A. K. Chem. Rev. 2003, 103, 3155.
(b) Brunel, J. M. Chem. Rev. 2005, 105, 857.
(c) Schenker, S.; Zamfir, A.; Freund, M.; Tsogoeva, S. B. Eur. J. Org. Chem. 2011, 2011, 2209.
[5] (a) Calloway, N. O. Chem. Rev. 1935, 17, 327.
(b) Tanaka, K. Transition-metal-mediated Aromatic Ring Construction, Wiley, Hoboken, NJ, 2013.
(c) Sunke, R.; Nallapati, S. B.; Kumar, J. S.; Kumarb, K. S.; Pal, M. Org. Biomol. Chem. 2017, 15, 4042.
[6] (a) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457.
(b) Saito, S.; Yamamoto, Y. Chem. Rev. 2000, 100, 2901.
(c) Kotha, S.; Misra, S.; Halder, S. Tetrahedron 2008, 64, 10775.
(d) Nicolaou, K. C.; Bulger, P. G.; Sarlah, D. Angew. Chem., Int. Ed. 2005, 44, 4442.
[7] (a) van Otterlo, W. A.; De Koning, C. B. Chem. Rev. 2009, 109, 3743.
(b) Saito, S.; Salter, M. M.; Gevorgyan, V.; Tsuboya, N.; Tando, K.; Yamamoto, Y. J. Am. Chem. Soc. 1996, 118, 3970.
(c) Gevorgyan, V.; Takeda, A.; Yamamoto, Y. J. Am. Chem. Soc. 1997, 119, 11313.
(d) Gevorgyan, V.; Sadayori, N.; Yamamoto, Y. Tetrahedron Lett. 1997, 38, 8603.
[8] Ramachary, D. B.; Ramakumar, K.; Kishor, M. Tetrahedron Lett. 2005, 46, 7037.
[9] Ramachary, D. B.; Ramakumar, K.; Narayana, V. V. J. Org. Chem. 2007, 72, 1458.
[10] Hong, B. C.; Tseng, H. C.; Chen, S. H. Tetrahedron 2007, 63, 2840.
[11] Li, S. G.; Hu, X. Q.; Jia, Z. X.; Xu, P. F. Tetrahedron 2010, 66, 8557.
[12] Wang, H.; Li, L.; Lin, W.; Xu, P.; Huang, Z.; Shi, D. Org. Lett. 2012, 14, 4598.
[13] Song, X.; Zhang, X.; Zhang, S.; Li, H.; Wang, W. Chem.-Eur. J. 2012, 18, 9770.
[14] Link, A.; Sparr, C. Angew. Chem., Int. Ed. 2014, 53, 1.
[15] Fäseke, V. C.; Sparr, C. Angew. Chem., Int. Ed. 2016, 55, 7261.
[16] Magar, K. B. S.; Xia, L.; Lee, Y. R. Chem. Commun. 2015, 51, 8592.
[17] Ponra, S.; Vitale, M. R.; Michelet, V.; Ratovelomanana-Vidal, V. J. Org. Chem. 2015, 80, 3250.
[18] Jiang, L.; Li, H.; Zhou, J. F.; Yuan, M. W.; Li, H. L.; Chuan, Y. M.; Yuan, M. L. Synth. Commun. 2018, 48, 336.
[19] Liu, J. Y.; Yang, X. C.; Liu, Z.; Luo, Y. C.; Lu, H.; Gu, Y. C.; Fang, R.; Xu, P. F. Org. Lett. 2019, 21, 5219.
[20] (a) Nair, V.; Pillai, A. N.; Beneesh, P. B.; Suresh, E. Org. Lett. 2005, 7, 4625.
(b) Nair, V.; Vidya, N.; Biju, A. T.; Deepthi, A.; Abhilash, K. G.; Suresh, E. Tetrahedron 2006, 62,10136.
[21] (a) Zhou, Q. F.; Yang, F.; Guo, Q. X.; Xue, S. Synlett 2007, 2073.
(b) Hu, B.; Meng, L. G.; Liu, Y. L.; Liang, M.; Xue, S. Synthesis 2009, 24, 4137.
[22] Talhi, O.; Makhloufi-Chebli, M.; Pinto, D. C.; Hamdi, M.; Silva, A. M. Synlett 2013, 24, 2559.
[23] Babu, G. N.; Ayalew, H. M.; Jain, S. Med. Chem. Res. 2014, 23, 2608.
[24] Moliterno, M.; Cari, R.; Puglisi, A.; Antenucci, A.; Sperandio, C.; Moretti, E.; Di Sabato, A.; Salvio, R.; Bella, M. Angew. Chem., Int. Ed. 2016, 55, 6525.
[25] Hu, Z.; Dong, J.; Men, Y.; Li, Y.; Xu, X. Chem. Commun. 2017, 53, 1739.
[26] (a) Enders, D.; Balensiefer, T. Acc. Chem. Res. 2004, 37, 534.
(b) Marion, N.; Diez-Gonzalez, S.; Nolan, S. P. Angew. Chem., Int. Ed. 2007, 46, 2988.
(c) Nair, V.; Vellalath, S.; Babu, B. P. Chem. Soc. Rev. 2008, 37, 2691.
(d) Bugaut, X.; Glorius, F. Chem. Soc. Rev. 2012, 41, 3511.
(e) Hopkinson, M. N.; Richter, C.; Schedler, M.; Glorius, F. Nature 2014, 510, 485.
(f) Flanigan, D. M.; Romanov-Michailidis, F.; White, N. A.; Rovis, T. Chem. Rev. 2015, 115, 9307.
(g) Zhang, C.; Hooper, J. F.; Lupton, D. W. ACS Catal. 2017, 7, 2583.
(h) Zhao, M.; Zhang, Y.-T.; Chen, J.; Zhou, L. Asian J. Org. Chem. 2018, 7,54.
[27] Zhu, T. S.; Zheng, P. C.; Mou, C. L.; Yang, S.; Song, B. A.; Chi, Y. R. Nat. Commun. 2014, 5, 6.
[28] Zhu, T. S.; Mou, C. L.; Li, B. S.; Smetankova, M.; Song, B. A.; Chi, Y. R. J. Am. Chem. Soc. 2015, 137, 5658.
[29] Huang, X.; Zhu, T.; Huang, Z.; Zhang, Y.; Jin, Z.; Zanoni, G.; Chi, Y. R. Org. Lett. 2017, 19, 6188.
[30] Wu, J.; Mou, C.; Chi, Y. R. Chin. J. Chem. 2018, 36, 333.
[31] Zhu, T.; Liu, Y.; Smetankova, M.; Zhuo, S.; Mou, C.; Chai, H.; Jin, Z.; Chi, Y. R. Angew. Chem., Int. Ed. 2019, 58, 15778.
[32] Hu, J. M.; Zhang, J. Q.; Sun, B. B.; Chen, J. B.; Yu, J. Q.; Yang, X. P.; Lv, H. P.; Wang, Z.; Wang, X. W. Org. Lett. 2019, 21, 8582.
[33] Candish, L.; Levensa, A.; Lupton, D. W. Chem. Sci. 2015, 6, 2366.
[34] Jia, Q.; Wang, J. Org. Lett. 2016, 18, 2212.
[35] Zhang, C. L.; Gao, Z. H.; Liang, Z. Q.; Ye, S. Adv. Synth. Catal. 2016, 358, 2862.
[36] Zhang, C. L.; Ye, S. Org. Lett. 2016, 18, 6408.
[37] Liu, J.; Das, D. K.; Zhang, G.; Yang, S.; Zhang, H.; Fang, X. Org. Lett. 2018, 20, 64.
[38] Liu, D.; Gao, Y.; Huang, J.; Fu, Z.; Huang, W. J. Org. Chem. 2018, 83, 14210.
[39] Chen, K. Q.; Luo, Z.; Gao, Z. H.; Ye, S. Chem.-Eur. J. 2019, 25, 3253.
[40] Xu, K.; Li, W.; Zhu, S.; Zhu, T. Angew. Chem., Int. Ed. 2019, 58, 17625.
[41] (a) Chen, Y.; Yekta, S.; Yudin, A. K. Chem. Rev. 2003, 103, 3155.
(b) Brunel, J. M. Chem. Rev. 2005, 105, 857.
(c) Renzi, P. Org. Biomol. Chem. 2017, 15, 4506.
(d) Witzig, R. M.; Lotter, D.; Fäseke, V. C.; Sparr, C. Chem.-Eur. J. 2017, 23,12960.
(e) Link, A.; Sparr, C. Chem. Soc. Rev. 2018, 47, 3804.
[42] Chen, Y. H.; Cheng, D. J.; Zhang, J.; Wang, Y.; Liu, X. Y.; Tan, B. J. Am. Chem. Soc. 2015, 137, 15062.
[43] Chen, Y. H.; Qi, L. W.; Fang, F.; Tan, B. Angew. Chem., Int. Ed. 2017, 56, 16308.
[44] Gao, H.; Xu, Q. L.; Keene, C.; Yousufuddin, M.; Ess, D. H.; Kürti, L. Angew. Chem., Int. Ed. 2016, 55, 566.
[45] Wang, J. Z.; Zhou, J.; Xu, C.; Sun, H.; Kürti, L.; Xu, Q. L. J. Am. Chem. Soc. 2016, 138, 5202.
[46] Saha, S.; Banerjee, A.; Maji, M. S. Org. Lett. 2018, 20, 6920.
[47] Lu, D. L.; Chen, Y. H.; Xiang, S. H.; Yu, P.; Tan, B.; Li, S. Org. Lett. 2019, 21, 6000.
[48] Liu, L.; Wei, L.; Zhang, J. Adv. Synth. Catal. 2010, 352, 1920.
[49] Zheng, X.; Lv, L.; Lu, S.; Wang, W.; Li, Z. Org. Lett. 2014, 16, 5156.
[50] Bu, M. J.; Lu, G. P.; Cai, C. Org. Chem. Front. 2016, 3, 630.
[51] Reddy, C. R.; Dilipkumar, U.; Shravya, R. Chem. Commun. 2017, 53, 1904.
[52] Xiao, T.; Dong, X.; Tang, Y.; Zhou, L. Adv. Synth. Catal. 2012, 354, 3195.