Chinese Journal of Organic Chemistry >
Advances of Iron(III) Chloride-Catalyzed Organic Reactions
Received date: 2012-07-28
Revised date: 2012-09-06
Online published: 2012-09-10
Supported by
Project supported by the National Natural Science Foundation of China (No.21042002) and the Natural Science Foundation of Shaanxi Province (No. 2010JM2001).
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
Song Yang , Tang Xuesong , Hou Xiaomeng , Bai Yinjuan . Advances of Iron(III) Chloride-Catalyzed Organic Reactions[J]. Chinese Journal of Organic Chemistry, 2013 , 33(01) : 76 -89 . DOI: 10.6023/cjoc201207044
[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.
/
| 〈 |
|
〉 |