三氯化铁催化的有机反应研究进展

doi:10.6023/cjoc201207044

摘要/Abstract

应用FeCl₃催化有机反应, 已经成为有机合成中的一个重要方法. 近年来一直是有机化学和催化化学的研究热点之一. 按照反应类型的不同对近年来三氯化铁催化的有机反应研究进展进行了综述.

Using FeCl₃ to catalyze organic reactions has become an important method in organic synthesis. It is a research hotspot in the field of the organic chemistry and catalytic chemistry recently. This comprehensive review attempts to cover the recent progress of FeCl₃-catalyzed organic reactions according to the different types of reactions.

Key words: FeC1₃, catalysis, organic reaction

引用此文

宋阳, 唐雪松, 侯晓萌, 白银娟. 三氯化铁催化的有机反应研究进展[J]. 有机化学, 2013, 33(01): 76-89.

Song Yang, Tang Xuesong, Hou Xiaomeng, Bai Yinjuan. Advances of Iron(III) Chloride-Catalyzed Organic Reactions[J]. Chin. J. Org. Chem., 2013, 33(01): 76-89.

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参考文献

[1] Bolm, C.; Legros, J.; Paih, J. L.; Zani, L. Chem. Rev. 2004, 104, 6217.

[2] Liu, L. -X. Curr. Org. Chem. 2010, 14, 1099.

[3] Chari, M. A.; Syamasundar, K. Catal. Commun. 2005,6, 67.

[4] Liu, C.-S.; Zhou, H.-X.; He, M.; Luo, G.-X. J. Liaoning Univ. Petroleum Chem. Technol. 2005, 25, 17 (in Chinese). (刘春生, 周海霞, 何淼, 罗根祥, 辽宁石油化工大学学报, 2005, 25, 17.)

[5] Li, S.-J.; Zhang, X.-M. Anhui Chem. Ind. 2006, 3, 17 (in Chinese). (黎少君, 张雪梅, 安徽化工, 2006, 3, 17.)

[6] Xie, B.; Chen, F.-E. Chin. J. Med. Chem. 2008, 18, 109 (in Chinese). (谢斌, 陈芬儿, 中国药物化学杂志, 2008, 18, 109.)

[7] Li, Y.-Q. Chin. J. Org. Chem. 2001, 21, 211 (in Chinese). (李毅群, 有机化学, 2001, 21, 211.)

[8] Yan, D.-M.; Liao, S.-G.; Sun, S.-D. J. Jilin Normal Univ. (Nat. Sci. Ed.) 2005, 2, 34 (in Chinese). (严德明, 廖世国, 孙顺丹, 吉林师范大学学报(自然科学版), 2005, 2, 34.)

[9] He, M.; Zhou, H.-X.; Liu, C.-S.; Luo, G.-X. Chin. J. Appl. Chem. 2006, 23, 343 (in Chinese). (何淼, 周海霞, 刘春生,罗根祥, 应用化学, 2006, 23, 343.)

[10] Humbeck, J. F. V.; Simonovich, S. P.; Knowles, R. R.; MacMillan, D. W. C. J. Am. Chem. Soc. 2010, 132, 10012.

[11] Bonnamour, J.; Bolm, C. Org. Lett. 2008, 10, 2665.

[12] Hatakeyama, T.; Nakagawa, N.; Nakamura, M. Org. Lett. 2009, 11, 4496.

[13] Carril, M.; Correa, A.; Bolm, C. Angew. Chem. 2008, 120, 4940.

[14] Liu, W.; Lei, A.-W. Tetrahedron Lett. 2008, 49, 610.

[15] Jiang, H.-F.; Li, J.-H.; Chen, Z.-W. Tetrahedron 2010, 66, 9721.

[16] Wei, H.-X.; Kim, S. H.; Li, G.-G. J. Org. Chem. 2002, 67, 4777.

[17] Yao, B.-B.; Liang,Z.-J.; Niu, T.-M.; Zhang, Y.-H. J. Org. Chem. 2009, 74, 4630.

[18] Maeda, S.; Horikawa, N.; Obora, Y.; Ishii, Y. J. Org. Chem. 2009, 74, 9558.

[19] Fan, J.-M.; Wan, C.-F.; Sun, G.-J.; Wang, Z.-Y. J. Org. Chem. 2008, 73, 8608.

[20] Benfatti, F.; Nanteuil, F.; Waser, J. Org. Lett. 2012, 14, 386.

[21] Bu, X.-L.; Zhang, Z.-X.; Zhou, X.-G. Organometallics 2010, 29, 3530.

[22] Huang, D.-S.; Wang, H.-N.; Xue, F.-Z.; Shi, Y.-A. J. Org. Chem. 2011, 76, 7269.

[23] Saino, N.; Kogure, D.; Okamoto, S. Org. Lett. 2005, 7, 3065.

[24] Marquié, J.; Laporterie, A.; Dubac, J. J. Org. Chem. 2001, 66, 421.

[25] Li, H.-J.; Li, W.-J.; Li, Z.-P. Chem. Commun. 2009, 3264.

[26] Duan, Z.; Xuan, X.-J.; Wu, Y.-J. Tetrahedron Lett. 2007, 48, 5157.

[27] Zou, T.; Pi, S.-S.; Li, J.-H. Org. Lett. 2009, 11, 453.

[28] Asthalter, T.; Rajagopalan, S.; Kauf, T.; Rabe, V.; Christoffers, J. J. Phys. Chem. A 2008, 112,11514.

[29] Christoffers, J.; Mann, A. Angew. Chem., Int. Ed. 2000, 39, 2752.

[30] Kischel, J.; Jovel, I.; Mertins, K.; Zapf, A.; Beller, M. Org. Lett. 2006, 8, 19.

[31] Li, R.-S.; Wang, S. R.; Lu, W.-J. Org. Lett. 2007, 9, 2219.

[32] Li, Z.-F.; Yang, C.-J.; Zheng, H.-F.; Qiu, H.-Y.; Lai, G.-Q. Chin. J. Org. Chem. 2009, 29, 403 (in Chinese) (李志芳, 杨成军, 郑红芳, 邱化玉, 来国桥, 有机化学, 2009, 29, 403.)

[33] Thirupathi, P.; Kim, S. S. J. Org. Chem. 2010, 75, 5240.

[34] Jana, U.; Maiti, S.; Biswas, S. Tetrahedron Lett. 2007, 48, 7160.

[35] Sheng, C.-J.; Li, Z.-F.; Yang, C.-J.; Lai, G.-Q.; Qiu, H.-Y. Chin. J. Org. Chem. 2008, 28, 515 (in Chinese). (盛春荠, 李志芳, 杨成军, 来国桥, 邱化玉, 有机化学, 2008, 28, 515.)

[36] Zhan, Z.-P.; Yu, J.-L.; Liu, H.-J.; Cui, Y.-Y.; Yang, R.-F.; Yang, W.-Z.; Li, J.-P. J. Org. Chem. 2006, 71, 8298.

[37] Yan, W.-M.; Wang, Q.-Y.; Chen, Y.-F.; Petersen, J. L.; Shi, X.-D. Org. Lett. 2010, 12,3308.

[38] Mantri, K.; Nakamura, R.; Komura, K.; Sugi, Y. Chem. Lett. 2005, 34, 1502.

[39] Ieda, N.; Mantri, K.; Miyata, Y.; Ozaki, A.; Komura, K.; Sugi, Y. Ind. Eng. Chem. Res. 2008, 47, 8631.

[40] He, Z.-L. The Principle of the Hard and Soft Acid/Base in Organic Chemistry, Science Press, Beijing, 1987, pp. 10～13 (in Chinese). (何子乐, 有机化学中的软硬酸碱原理, 科学出版社, 北京, 1987, pp. 10～13.)

[41] Liu, Z.-Q.; Zhang, Y.-X.; Zhao, L.-X.; Li, Z.-J.; Wang, J.-T.; Li, H.-J.; Wu, L.-M. Org. Lett. 2011, 13, 2208.

[42] Ito, S.; Fujiwara, Y.-I.; Nakamura, E.; Nakamura, M. Org. Lett. 2009, 11, 4306.

[43] Noda, D.; Sunada, Y.; Hatakeyama, T.; Nakamura, M.; Nagashima, H. J. Am. Chem. Soc. 2009, 131, 6078.

[44] Chinchilla, R.; Nájera, C. Chem. Rev. 2007, 107, 874.

[45] Jana, U.; Biswas, S.; Maiti, S. Eur. J. Org. Chem. 2008, 2008, 5798.

[46] Hatakeyama, T.; Yoshimoto, Y.; Gabriel, T.; Nakamura, M. Org. Lett. 2008, 10, 5341.

[47] Gøgsig, T. M.; Lindhardt, A. T.; Skrydstrup, T. Org. Lett. 2009, 11, 4886.

[48] Tran, L. D.; Daugulis, O. Org. Lett. 2010, 12, 4277.

[49] Hamze, A.; Brion, J. D.; Alami, M. Org. Lett. 2012, 14, 2782.

[50] Liu, W.; Cao, H.; Lei, A.-W. Angew. Chem. 2010, 122, 2048.

[51] Chandrasekharam, M.; Chiranjeevi, B.; Gupta, K. S. V.; Sridhar, B. J. Org. Chem. 2011, 76, 10229.

[52] Bica, K.; Gaertner, P. Org. Lett. 2006, 8, 733.

[53] Hatakeyama, T.; Nakamura, M. J. Am. Chem. Soc. 2007, 129, 9844.

[54] Cahiez, G.; Chaboche, C.; Betzer, F. M.; Ahr, M. Org. Lett. 2005, 7, 1943.

[55] Wang, K.-L.; Lü, M.-Y.; Yu, A.; Zhu, X.-Q.; Wang, Q.-M. J. Org. Chem. 2009, 74,935.

[56] Shirakawa, E.; Uchiyama, E.; Hayashi, T. J. Org. Chem. 2011, 76, 25.

[57] Kumaraswamy, G.; Murthy, A. N.; Pitchaiah, A. J. Org. Chem. 2010, 75, 3916.

[58] Carballo, R. M.; Purino, M.; Rami?rez, M. A.; Marti?n, V. S.; Padro?n, J. I. Org. Lett. 2010, 12, 5334.

[59] Huang, W.; Zheng, P.-Z.; Zhang, Z.-X.; Liu, R.-T.; Chen, Z.-X.; Zhou, X.-G. J. Org. Chem. 2008, 73, 6845.

[60] Chan, L.-Y.; Kim, S.; Park, Y.; Lee, P. H. J. Org. Chem. 2012, 77, 5239.

[61] Taniguchi, T.; Goto, N.; Nishibata, A.; Ishibashi, H. Org. Lett. 2010, 12, 112.

[62] Yang, L.; Lei, C.-H.; Wang, D.-X.; Huang, Z.-T.; Wang, M.-X. Org. Lett. 2010, 12, 3918.

[63] Guérinot, A.; Muns, A. S.; Gnamm, G.; Bensoussan, C.; Reymond, S.; Cossy, J. Org. Lett. 2010, 12, 1808.

[64] Du, Y.-F.; Chang, J.-B.; Reiner, J.; Zhao, K. J. Org. Chem. 2008, 73, 2007.

[65] Yang, D.-S.; Fu, H.; Hu, L.-M.; Jiang, Y.-Y.; Zhao, Y.-F. J. Comb. Chem. 2009, 11, 653.

[66] Tang, L.-N.; Pang, Y.-L.; Yan, Q.; Shi, L.-Q.; Huang, J.-H.; Du, Y.-F.; Zhao, K. J. Org. Chem. 2011, 76, 2744.

[67] Zhan, Z.-P.; Cai, X.-B.; Wang, S.-P.; Yu, J.-L.; Liu, H.-J.; Cui, Y.-Y. J. Org. Chem. 2007, 72, 9838.

[68] Liang, Z.-D.; Hou, W.-Z.; Du, Y.-F.; Zhang, Y.-L.; Pan, Y.; Mao, D.; Zhao, K. Org. Lett. 2009,11,4978.

[69] Gay, R. M.; Manarin, F.; Schneider, C. C.; Barancelli, D. A.; Costa, M. D.; Zeni, G. J. Org. Chem. 2010, 75, 5701.

[70] Bera, K.; Sarkar, S.; Biswas, S.; Maiti, S.; Jana, U. J. Org. Chem. 2011, 76, 3539.

[71] Liu, C.-R.; Yang, F.-L.; Jin, Y.-Z.; Ma, X.-T.; Cheng, D.-J.; Li, N.; Tian, S.-K. Org. Lett. 2010, 12, 3832.

[72] Xu, X.-B.; Xu, X.-L.; Li, H.-F.; Xie, X.; Li, Y.-Z. Org. Lett. 2010, 12, 100.

[73] Li, H.-F.; Yang, J.-Y.; Liu, Y.-H.; Li, Y.-Z. J. Org. Chem. 2009, 74, 6797.

[74] Wang, J.-L.; Huang, W.; Zhang, Z.-X.; Xiang, X.; Liu, R.-T.; Zhou, X.-G. J. Org. Chem. 2009, 74, 3299.

[75] Shevelev, S. A.; Shakhnes A. K.; Ugrak B. I.; Vorobéva, S. S. Synth. Commun. 2001, 31, 2557.

[76] Dömling, A. Chem. Rev. 2006, 106, 17.

[77] Maiti, S.; Biswas, S.; Jana, U. J. Org. Chem. 2010, 75, 1674.

[78] Li, P.-H.; Zhang, Y.-C.; Wang, L. Chem. Eur. J. 2009, 15, 2045.

[79] Lu, J.; Bai, Y.-J. Synthesis 2002, 466.

[80] Li, Q.-J.; Shi, M.; Timmons, C.; Li, G.-H. Org. Lett. 2006, 8, 625.

[81] Wang, Y.-M.; Bi, X.-H.; Li, W.-Q.; Li, D.-H.; Zhang, Q.; Liu, Q.; Ondon, B. S. Org. Lett. 2011, 13,1722.

[82] Nakamura, M.; Matsuo, K.; Inoue, T.; Nakamura, E. Org. Lett. 2003, 5, 1373.

[83] Huang, L.-H.; Cheng, K.; Yao, B.-B.; Xie, Y.-J.; Zhang, Y.-H. J. Org. Chem. 2011, 76, 5732.

[84] Yan, W.-M.; Ye, X.-H.; Akhmedov, N. G.; Petersen, J. L.; Shi, X.-D. Org. Lett. 2012, 14, 2358.

[85] Bian, Y.-J.; Jia, Z.-Q. Chin. J. Org. Chem. 2009, 29, 975 (in Chinese). (边延江, 贾志强, 有机化学, 2009, 29, 975.)

[86] Zhang, Y.-C.; Wang, M.; Li, P.-H.; Wang, L. Org. Lett. 2012, 14, 2206.

[87] Guo, X.-W.; Yu, R.; Li, H.-J.; Li, Z.-P. J. Am. Chem. Soc. 2009, 131, 17387.