无过渡金属参与的1,2,3-三唑合成进展

doi:10.6023/cjoc201601020

摘要/Abstract

因其特殊结构和化学性质，1，2，3-三唑已成为一个药物、农药、染料和材料分子中重要的结构基元而备受关注. 尽管过渡金属催化下的三唑合成取得了巨大的进展，但过渡金属本身多具毒性、对环境存在潜在的污染，因此，无过渡金属参与下开发新颖、高效、便捷的合成方法构建1，2，3-三唑已成为有机化学领域内备受关注的研究课题. 结合我们小组的研究兴趣和工作，综述了2010年以来无过渡金属参与的1，2，3-三唑合成方法进展.

关键词: 1,2,3-三唑, 无过渡金属, 合成方法

Because of its unique structure and chemical characteristics, 1,2,3-triazole was increasingly considered as an important structural motif in pharmaceuticals, agrochemicals, dyes and materials. Recently, main progress has been achieved under transition metal-catalysis. Considering the toxicity and potentially environmental pollution of transition metals, the novel, efficient and convenient synthetic methodologies of 1,2,3-triazole under transition metal-free conditions have been received widely attention. Based on our work and research interesting, the aim of this review is to give an overview of the progress on the diverse synthetic methodologies of 1,2,3-triazole with transition metal-free since 2010.

Key words: 1,2,3-triazole, transition metal-free, synthetic methods

引用此文

陈昱学, 郑超, 彭潇楚, 符青坛, 吴禄勇, 林强. 无过渡金属参与的1,2,3-三唑合成进展[J]. 有机化学, 2016, 36(8): 1779-1789.

Chen Yuxue, Zheng Chao, Peng Xiaochu, Fu Qingtan, Wu Luyong, Lin Qiang. Research Progress in the Synthesis of 1,2,3-Triazole under Transition-Metal-Free[J]. Chin. J. Org. Chem., 2016, 36(8): 1779-1789.

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参考文献

[1] (a) Krivopalov, V. P.; Shkurko, O. P. Russ. Chem. Rev. 2005, 74, 339.
(b) Tome, A. C. In Science of Synthesis, Vol. 13, Eds.: Stor, R.; Gilchrist, T. Thieme, New York, 2004, p. 415.
(c) Jiang, Y.; Kuang, C. Proc. Chem. 2012, 24, 1983 (in Chinese).
(江玉波, 匡春香, 化学进展, 2012, 24, 1983.)
(d) Wang, J.; Li, L.; Zhang, G. Chin. J. Org. Chem. 2009, 29, 13 (in Chinese).
(王景梅, 李凌君, 张贵生, 有机化学, 2009, 29, 13.)
[2] Rostovtsev, V. V.; Green, L. G.; Fokin, V. V.; Sharpless, K. B. Angew. Chem., Int. Ed. 2002, 41, 2596.
[3] Tornøe, C. W.; Christensen, C.; Meldal, M. J. Org. Chem. 2002, 67, 3057.
[4] (a) Meldal; M.; Tornøe, C. W. Chem. Rev. 2008, 108, 2952.
(b) Boren, B. C.; Narayan, S.; Rasmussen, L. K.; Zhang, Li.; Zhao, H.; Lin, Z.; Jia, G.; Fokin, V. V. J. Am. Chem. Soc. 2008, 130, 8923.
(c) Barluenga, J.; Valdes, C.; Beltren, G.; Escribano, M.; Aznar, F. Angew. Chem., Int. Ed. 2006, 45, 6893.
[5] Baskin, J. M.; Prescher, J. A.; Laughlin, S. T.; Agard, N. J.; Chang, P. V.; Miller, I. A.; Lo, A.; Codelli, J. A.; Bertozzi, C. R. Proc. Natl. Acad. Sci. U. S. A. 2007, 104, 16793.
[6] Ning, X.; Guo, J.; Wolfert, M. A.; Boons, G.-J. Angew. Chem., Int. Ed. 2008, 47, 2253.
[7] Krasiński, A.; Fokin, V. V.; Sharpless, K. B. Org. Lett. 2004, 6, 1237.
[8] Kwok, S. W.; Fotsing, J. R.; Fraser, R. J.; Rodionov, V. O.; Fokin,V. V. Org. Lett. 2010, 12, 4217.
[9] Jiang, Y.; Kuang, C.; Yang, Q. Tetrahedron 2011, 67, 289.
[10] Meza-Aviña, M. E.; Patel, M. K.; Lee, C. B.; Dietz, T. J.; Croatt, M. P. Org. Lett. 2011, 13, 2984.
[11] Smith, C. D.; Greaney, M. F. Org. Lett. 2013, 15, 4826.
[12] Wu, L.; Chen, X.; Tang, M.; Song, X.; Chen, G.; Song, X.; Lin, Q. Synlett 2012, 23, 1529.
[13] Kloss, F.; Köhn, U.; Jahn, B. O.; Hager, M. D.; Görls, H.; Schubert, U. S. Chem. Asian J. 2011, 6, 2816.
[14] Li, J.; Zhang, Y.; Wang, D.; Wang, W.; Gao, T.; Wang, L.; Li, J.; Huang, G.; Chen, B. Synlett 2010, 1617.
[15] Cheng, G.; Zeng, X.; Shen, J.; Wang, X.; Cui, X. Angew. Chem., Int. Ed. 2013, 52, 13265.
[16] Zhang, H.; Tanimoto, H.; Morimoto, T.; Nishiyama, Y.; Kakiuchi, K. Org. Lett. 2013, 15, 5222.
[17] Quiclet-Sire, B.; Zard, S. Z. Synthesis 2005, 3319.
[18] Amantini, D.; Fringuelli, F.; Piermatti, O.; Pizzo, F.; Zunino, E.; Vaccaro, L. J. Org. Chem. 2005, 70, 6526.
[19] D'Ambrosio, G.; Fringuelli, F.; Pizzo, F.; Vaccaro, L. Green Chem. 2005, 7, 874.
[20] Wang, T.; Hu, X.-C.; Huang, X.-J.; Li, X.-S.; Xie, J.-W. J. Braz. Chem. Soc. 2012, 23, 1119.
[21] Quan, X.-J.; Ren, Z.-H.; Wang, Y.-Y.; Guan, Z.-H. Org. Lett. 2014, 16, 5728.
[22] Quan, X.-J.; Ren, Z.-H.; Wang, Y.-Y.; Guan, Z.-H. Org. Lett. 2015, 17, 393.
[23] Gao, Y.; Lam, Y. Org. Lett. 2006, 8, 3283.
[24] Dey, S.; Datta, D.; Pathak, T. Synlett 2011, 2521.
[25] Dey, S.; Pathak, T. RSC Adv. 2014, 4, 9275.
[26] Kayet, A.; Pathak, T. J. Org. Chem. 2013, 78, 9865.
[27] Kayet, A.; Dey, S.; Pathak, T. Tetrahedron Lett. 2015, 56, 5521.
[28] Bhaumik, A.; Samanta, S.; Pathak, T. J. Org. Chem. 2014, 79, 6895.
[29] Sahu, D.; Dey, S.; Pathak, T.; Ganguly, B. Org. Lett. 2014, 16, 2100.
[30] Alcaide, B.; Almendros, P.; Lázaro-Milla, C. Chem. Commun. 2015, 51, 6992.
[31] Li, W.; Wang, J. Angew. Chem., Int. Ed. 2014, 53, 14186.
[32] Li, W.; Du, Z.; Zhang, K.; Wang, J. Green Chem. 2015, 17, 781.
[33] Wan, J.-P.; Cao, S.; Liu. Y. J. Org. Chem. 2015, 80, 9028.
[34] Rogue, D. R.; Neill, J. L.; Antoon, J. W.; Stevens, E. P. Synthesis 2005, 2497.
[35] Hansen, S. G.; Jensen, H. H. Synlett 2009, 3275.
[36] Wu, L.; Chen, Y.; Luo, J.; Sun, Q.; Peng, M.; Lin, Q. Tetrahedron Lett. 2014, 55, 3847.
[37] Augustine, J. K.; Boodappa, C.; Venkatachaliah, S. Org. Biomol. Chem. 2014, 12, 2280.
[38] Penthala, N. R.; Madadi, N. R.; Janganati, V.; Crooks, P. A. Tetrahedron Lett. 2014, 55, 5562.
[39] Ramachary, D. B.; Ramakumar, K.; Narayana, V. V. Chem. Eur. J. 2008, 14, 9143.
[40] Ramachary, D. B.; Shashank, A. B. Chem. Eur. J. 2013, 19, 13175.
[41] Danence, L. J. T.; Gao, Y.; Li, M.; Huang, Y.; Wang, J. Chem. Eur. J. 2011, 17, 3584.
[42] Krishna, P. M.; Ramachary, D. B.; Peesapatia, S. RSC Adv. 2015, 62062.
[43] Belkheira, M.; Abed, D. E.; Pons, J.-M.; Bressy, C. Chem. Eur. J. 2011, 17, 12917.
[44] Wang, L.; Peng, S.; Danence, L. J. T.; Gao, Y.; Wang, J. Chem. Eur. J. 2012, 18, 6088.
[45] Li, W.; Jia, Q.; Du, Z.; Wang, J. Chem. Commum. 2013, 49, 10187.
[46] Ramachary, D. B.; Shashank, A. B.; Karthik, S. Angew. Chem., Int. Ed. 2014, 53, 10420.
[47] Shashank, A. B.; Karthik, S.; Madhavachary, R.; Ramachary, D. B. Chem. Eur. J. 2014, 20, 16877.
[48] Ramachary, D. B.; Krishna, P. M.; Gujral, J.; Reddy, G. S. Chem. Eur. J. 2015, 21, 16775.
[49] Jia, Q.; Yang, G.; Chen, L.; Du, Z.; Wei, J.; Zhong, Y.; Wang, J. Eur. J. Org. Chem. 2015, 3435.
[50] Sengupta, S.; Duan, H.; Lu, W.; Petersen, J. L.; Shi, X. Org. Lett. 2008, 10, 1493.
[51] Ponpandian, T.; Muthusubramanian, S. Tetrahedron Lett. 2012, 53, 59.
[52] Ali, A.; Corrêa, A. G.; Alves, D.; Zukerman-Schpector, J.; Westermann, B.; Ferreiraa, M. A. B.; Paixão, M. W. Chem. Commun. 2014, 50, 11926.
[53] Chai, H.; Guo, R.; Yin, W.; Cheng, L.; Liu, R.; Chu, C. ACS Comb. Sci. 2015, 17, 147.
[54] Maurya, R. A.; Adiyala, P. R.; Chandrasekhar, D.; Reddy, C. N.; Kapure, J. S.; Kamal, A. ACS Comb. Sci. 2014, 16, 466.
[55] John, J.; Thomas, J.; Parekh, N.; Dehaen, W. Eur. J. Org. Chem. 2015, 4922.
[56] Thomas, J.; John, J.; Parekh, N.; Dehaen, W. Angew. Chem., Int. Ed. 2014, 53, 10155.
[57] Wu, L.; Wang, X.; Chen, Y.; Huang, Q.; Lin, Q.; Wu, M. Synlett 2016, 27, 437.
[58] González-Calderón, D.; Santillán-Iniesta, I.; González-González, C. A.; Fuentes-Benítes, A.; González-Romero, C. Tetrahedron Lett. 2015, 56, 514.
[59] González-Calderón, D.; Paz, J. G. A.-D.; González-González, C. A.; Fuentes-Benítes, A.; González-Romero, C. Tetrahedron Lett. 2015, 56, 1713.
[60] Sakai, K.; Hida, N.; Kondo, K. Bull. Chem. Soc. Jpn. 1986, 59, 179.
[61] van Berkel, S. S.; Brauch, S.; Gabriel, L.; Henze, M.; Stark, S.; Vasilev, D.; Wessjohann, L. A.; Abbas, M.; Westermann, B. Angew. Chem., Int. Ed. 2012, 51, 5343.
[62] Cai, Z.-J.; Lu, X.-M.; Zi, Y.; Yang, C.; Shen, L.-J.; Li, J.; Wang S.-Y.; Ji, S.-J. Org. Lett. 2014, 16, 5108.
[63] Chen, Z.; Yan, Q.; Liu, Z.; Zhang, Y. Chem. Eur. J. 2014, 20, 17635.
[64] Bai, H.-W.; Cai, Z.-J.; Wang, S.-Y.; Ji S.-J. Org. Lett. 2015, 17, 2898.
[65] Chen, J.-H.; Liu, S.-R.; Chen, K. Chem. Asian J. 2010, 5, 328.
[66] Mani, N. S.; Fitzgerald A. E. J. Org. Chem. 2014, 79, 8889.
[67] He, Y.; Sun, E.; Zhao, Y.; Hai, L.; Wu, Y. Tetrahedron Lett. 2014, 55, 111.
[68] Kazancioglu, E. A.; Kazancioglu, M. Z.; Fistikci, M.; Secen, H.; Altundas, R. Org. Lett. 2013, 15, 4790.
[69] Loren, J. C.; Sharpless, K. B. Synthesis 2005, 1514.