Citation: He Xinwei, Hu Xiaoqian, Tao Jiajia, Han Guang, Shang Yongjia. Progress in Iron Complexes-Catalyzed Organic Reactions[J]. Chinese Journal of Organic Chemistry, ;2016, 36(7): 1465-1483. doi: 10.6023/cjoc201601007 shu

Progress in Iron Complexes-Catalyzed Organic Reactions

1.
College of Chemistry and Materials Science, Anhui Normal University, Wuhu 241000

Corresponding author: He Xinwei, xinweihe@mail.ahnu.edu.cn Shang Yongjia, shyj@mail.ahnu.edu.cn
Received Date: 8 January 2016
Revised Date: 3 March 2016

Fund Project: the Natural Science Foundation of Anhui Province No. 1308085QB39the National Natural Science Foundation of China Nos. 21172001, 21372008the Doctoral Scientific Research Foundation of Anhui Normal University No. 2016XJJ110

Figures(22)

In recent years, metal and their complexes-catalyzed organic reactions have received much attention in organic chemistry due to their rapidity and efficiency. Iron complexes have attracted much attention from chemical society due to the advantages of high catalytic activity and selectivity. The advances of iron complexes-catalyzed organic reactions are reviewed, such as polymerisation reactions, hydrosilylation/hydroboration, cycloaddition, redox reactions, cross-coupling reactions and 1,4-additions, and the prospects of its development are forecasted.
- catalysis,
- iron complexe,
- organic reaction,
- research progress
1. [1]
  Reppe, W. Experientia 1949, 5, 93.
2. [2]
  Kealy, T. J.; Pauson, P. L. Nature 1951, 168, 1039.
3. [3]
  Hieber, V. W.; Braun, G. Z. Naturforsch. 1959, 146, 132.
4. [4]
  Bolm, C.; Legros, J.; Le Paih, J.; Zani, L. Chem. Rev. 2004, 104, 6217.
5. [5]
  Rose, E.; Andrioletti, B.; Zrig, S.; Quelquejeu-Ethève, M. Chem. Soc. Rev. 2005, 34, 573. (b) Correa, A.; García Mancheño, O.; Bolm, C. Chem. Soc. Rev. 2008, 37, 1108. (c) Sun, C.-L.; Li, B.-J.; Shi, Z.-J. Chem. Rev. 2011, 111, 1293. (d) Gopalaiah, K. Chem. Rev. 2013, 113, 3248.
6. [6]
  Plietker, B. Iron Catalysis in Organic Chemistry: Reactions and Applications, Wiley-VCH, Weinheim, Germany, 2008. (b) Plietker, B. Topics in Organometallic Chemsitry, Iron Catalysis: Fundamentals and Applications, Springer-VBH, Berlin, 2011, Vol. 33.
7. [7]
  Gan, K.; Sadeer, A.; Xu, C.; Li, Y.; Pullarkat, S. A. Organometallics 2014, 33, 5074.
8. [8]
  Champouret, Y. D. M.; Fawcett, J.; Nodes, W. J.; Singh, K.; Solan, G. A. Inorg. Chem. 2006, 45, 9890. (b) Sun, W.-H.; Hao, P.; Zhang, S.; Shi, Q.; Zuo, W.; Tang, X.; Lu, X. Organometallics 2007, 26, 2720.
9. [9]
  Ma, J.; Feng, C.; Wang, S.; Zhao, K.-Q.; Sun, W.-H.; Redshaw, C.; Solan, G. A. Inorg. Chem. Front. 2014, 1, 14. (b) Searles, K.; Fortier, S.; Khusniyarov, M. M.; Carroll, P. J.; Sutter, J.; Meyer, K.; Mindiola, D. J.; Caulton, K. G. Angew. Chem., Int. Ed. 2014, 53, 14139. (c) Lin, Y.-F.; Ichihara, N.; Nakajima, Y.; Ozawa, F. Organometallics 2014, 33, 6700. (d) Suzuki, T.; Matsumoto, J.; Kajita, Y.; Inomata, T.; Ozawaa, T.; Masuda, H. Dalton Trans. 2015, 44, 1017.
10. [10]
  Zuo, W.; Tauer, S.; Prokopchuk, D. E.; Morris, R. H. Organometallics 2014, 33, 5791. (b) Cussó, O.; Garcia-Bosch, I.; Ribas, X.; Lloret-Fillol, J.; Costas, M. J. Am. Chem. Soc. 2013, 135, 14871.
11. [11]
  Zhang, Q.; Xiang, L.; Deng, L. Organometallics 2012, 31, 4537. (b) Gallego, D.; Inoue, S.; Blom, B.; Driess, M. Organometallics 2014, 33, 6885. (c) Bhattacharya, P.; Krause, J. A.; Guan, H. Organometallics 2014, 33, 6113.
12. [12]
  Karpiniec, S. S.; McGuinness, D. S.; Britovsek, G. J. P.; Wierengaa, T. S.; Patel, J. Chem. Commun. 2011, 47, 6945.
13. [13]
  Xing, Q.; Zhao, T.; Qiao, Y.; Wang, L.; Redshaw, C.; Sun, W.-H. RSC Adv. 2013, 3, 26184.
14. [14]
  Huang, F.; Xing, Q.; Liang, T.; Flisak, Z.; Ye, B.; Hu, X.; Yang, W.; Sun, W.-H. Dalton Trans. 2014, 43, 16818.
15. [15]
  Chen, J.; Xi, T.; Lu, Z. Org. Lett. 2014, 16, 6452.
16. [16]
  Chen, J.; Cheng, B.; Cao, M.; Lu, Z. Angew. Chem., Int. Ed. 2015, 54, 4661.
17. [17]
  Morris, R. H. Chem. Soc. Rev. 2009, 38, 2282.
18. [18]
  Bhattacharya, P.; Krause, J. A.; Guan, H. Organometallics 2014, 33, 6113.
19. [19]
  Zuo, Z.; Zhang, L.; Leng, X.; Huang, Z. Chem. Commun. 2015, 51, 5073.
20. [20]
  Bleith, T.; Wadepohl, H.; Gade, L. H. J. Am. Chem. Soc. 2015, 137, 2456.
21. [21]
  Ito, J.; Hosokawa, S.; Khalid, H. B.; Nishiyama, H. Organometallics 2015, 34, 1377.
22. [22]
  Zuo, Z.; Sun, H.; Wang, L.; Li, X. Dalton Trans. 2014, 43, 11716.
23. [23]
  Wu, S.; Li, X.; Xiong, Z.; Xu, W.; Lu, Y.; Sun, H. Organometallics 2013, 32, 3227. (b) Zhao, H.; Sun, H.; Li, X. Organometallics 2014, 33, 3535.
24. [24]
  Huang, S.; Zhao, H.; Li, X.; Wang, L.; Sun, H. RSC Adv. 2015, 5, 15660.
25. [25]
  Wang, L.; Sun, H.; Li, X. Eur. J. Inorg. Chem. 2015, 2732.
26. [26]
  Xue, B.; Sun, H.; Li, X. RSC Adv. 2015, 5, 52000.
27. [27]
  Zhang, C.; Yu, S.-B.; Hu, X.-P.; Wang, D.-Y.; Zheng, Z. Org. Lett. 2010, 12, 5542.
28. [28]
  Check, C. T.; Jang, K. P.; Schwamb, C. B.; Wong, A. S.; Wang, M. H.; Scheidt, K. A. Angew. Chem., Int. Ed. 2015, 54, 4264.
29. [29]
  Zhang, C.; Hu, X.-H.; Wang, Y.-H.; Zheng, Z.; Xu, J.; Hu, X.-P. J. Am. Chem. Soc. 2012, 134, 9585.
30. [30]
  Casitas, A.; Krause, H.; Goddard, R.; Fürstner, A. Angew. Chem., Int. Ed. 2015, 54, 1521.
31. [31]
  Cussó, O.; Ribas, X.; Lloret-Fillol, J.; Costas, M. Angew. Chem., Int. Ed. 2015, 54, 2729.
32. [32]
  Chatterjee, S.; Paine, T. K. Inorg. Chem. 2015, 54, 1720.
33. [33]
  Li, Y.; Yu, S.; Wu, X.; Xiao, J.; Shen, W.; Dong, Z.; Gao, J. J. Am. Chem. Soc. 2014, 136, 4031. (b) Li, Y.; Yu, S.; Shen, W.; Gao. J. Acc. Chem. Res. 2015, 48, 2587. (c) Yoshimura, M.; Tanaka, S.; Kitamura, M. Tetrahedron Lett. 2014, 55, 3635. (d) Foubelo, F.; Nájera, C.; Yus, M. Tetrahedron: Asymmetry 2015, 26, 769.
34. [34]
  Mikhailine, A. A.; Morris, R. H. Inorg. Chem. 2010, 49, 11039. (b) Lagaditis, P. O.; Lough, A. J.; Morris, R. H. Inorg. Chem. 2010, 49, 10057. (c) Meyer, N.; Lough, A. J.; Morris, R. H. Chem. Eur. J. 2009, 15, 5605. (d) Mikhailine, A.; Lough, A. J.; Morris, R. J. Am. Chem. Soc. 2009, 131, 1394. (e) Sui-Seng, C.; Freutel, F.; Lough, A. J.; Morris, R. Angew. Chem., Int. Ed. 2008, 47, 940.
35. [35]
  Sues, P. E.; Lough, A. J.; Morris, R. H. Organometallics 2011, 30, 4418.
36. [36]
  Mikhailine, A. A.; Maishan, M. I.; Lough, A. J.; Morris, R. H. J. Am. Chem. Soc. 2012, 134, 12266.
37. [37]
  Prokopchuk, D. E.; Sonnenberg, J. F.; Meyer, N.; Iuliis, M. Z.-D.; Lough, A. J.; Morris, R. H. Organometallics 2012, 31, 3056.
38. [38]
  Zuo, W.; Lough, A. J.; Li, Y. F.; Morris, R. H. Science 2013, 342, 1080.
39. [39]
  Prokopchuk, D. E.; Morris, R. H. Organometallics 2012, 31, 7375.
40. [40]
  Zuo, W.; Tauer, S.; Prokopchuk, D. E.; Morris, R. H. Organometallics 2014, 33, 5791.
41. [41]
  Sonnenberg, J. F.; Lough, A. J.; Morris, R. H. Organometallics 2014, 33, 6452.
42. [42]
  Lagaditis, P. O.; Sues, P. E.; Sonnenberg, J. F.; Wan, K. Y.; Lough, A. J.; Morris, R. H. J. Am. Chem. Soc. 2014, 136, 1367.
43. [43]
  Zuo, W.; Morris, R. H. Nat. Protoc. 2015, 10, 241.
44. [44]
  Smith, S. A. M.; Morris, R. H. Sythesis 2015, 47, 1775.
45. [45]
  Bigler, R.; Mezzetti, A. Org. Lett. 2014, 16, 6460.
46. [46]
  Mikhailine, A. A.; Maishan, M. I.; Morris, R. H. Org. Lett. 2012, 14, 4638.
47. [47]
  Mazza, S.; Scopelliti, R.; Hu, X. Organometallics 2015, 34, 1538.
48. [48]
  Kuwano, R.; Hashiguchi, Y.; Ikeda, R.; Ishizuka, K. Angew. Chem., Int. Ed. 2015, 54, 2393.
49. [49]
  Gan, K.; Sadeer, A.; Xu, C.; Li, Y.; Pullarkat, S. A. Organometallics 2014, 33, 5074.
50. [50]
  Hellmuth, T.; Frey, W.; Peters, R. Angew. Chem., Int. Ed. 2015, 54, 2788.
51. [51]
  Foo, K.; Sella, E.; Thomé, I.; Eastgate, M. D.; Baran, P. S. J. Am. Chem. Soc. 2014, 136, 5279.
52. [52]
  Green, R. A.; Hartwig, J. F. Angew. Chem., Int. Ed. 2015, 54, 3768.
53. [53]
  Borzenko, A.; Rotta-Loria, N. L.; MacQueen, P. M.; Lavoie, C. M.; McDonald, R.; Stradiotto, M. Angew. Chem., Int. Ed. 2015, 54, 3773.
54. [54]
  Yeung, C. S.; Dong, V. M. Chem. Rev. 2011, 111, 1215. (b) Jana, R.; Pathak, T. P.; Sigman, M. S. Chem. Rev. 2011, 111, 1417. (c) Cherney, A. H.; Kadunce, N. T.; Reisman, S. E. Chem. Rev. 2015, 115, 9587. (d) Liu, C.; Yuan, J.; Gao, M.; Tang, S.; Li, W.; Shi, R.; Lei, A. Chem. Rev. 2015, 115, 12138.
55. [55]
  Shang, Y.-J.; Wu, J.-W.; Fan, C.-L.; Hu, J.-S.; Lu, B.-Y. J. Organomet. Chem. 2008, 693, 2963.
56. [56]
  Feng, Z.-J.; Yu, S.-Y.; Shang, Y.-J. Appl. Organomet. Chem. 2008, 22, 577.
57. [57]
  Yu, S.-Y.; Zhang, Z.-Q.; Yu, Z.-Y.; Shang, Y.-J. Appl. Organomet. Chem. 2014, 28, 657.
58. [58]
  Mo, Z.; Zhang, Q.; Deng, L. Organometallics 2012, 31, 6518.
59. [59]
  Bauer, G.; Wodrich, M. D.; Scopelliti, R.; Hu, X. Organometallics 2015, 34, 289.
60. [60]
  Yang, H.; Yan, H.; Sun, P.; Zhu, Y.; Lu, L.; Liu, D.; Rong, G.; Mao, J. Green Chem. 2013, 15, 976.
61. [61]
  Zheng, J.; Darcel, C.; Sortais, J.-B. Chem. Commun. 2014, 50, 14229.
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