Citation: SONG Hong-Jin, LI Lu, ZHANG Ni, WANG Fei, LÜ Jing, MENG Xiang-Guang. Selective Epoxidation of Olefins Catalyzed by in Situ Prepared Iron(Ⅱ) Complex[J]. Chinese Journal of Inorganic Chemistry, ;2019, 35(2): 285-292. doi: 10.11862/CJIC.2019.046 shu

Selective Epoxidation of Olefins Catalyzed by in Situ Prepared Iron(Ⅱ) Complex

Key Laboratory of Green Chemistry and Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064, China

Corresponding author: MENG Xiang-Guang, mengxgchem@163.com
Received Date: 10 October 2018
Revised Date: 6 December 2018

Figures(4)

A ligand of 2-(2-pyridyl)-oxazoline(Pyrox) was prepared. The complex of containing Iron(Ⅱ) trifluome-thanesulfonate, Pyrox and another auxiliary ligand can be in situ formed in acetonitrile solution. Quantum chemistry calculations showed that the nitrogen rather than oxygen atom on the Pyrox coordinates with Iron. It was found the terminal aromatic and aliphatic olefins could be efficiently epoxidized with H₂O₂ catalyzed by this Iron complex in acetonitrile at room temperature. The reaction with good selectivity was rapid, mild and in an wide range of substrates. The influences of axial ligands, solvents and oxidants are sensitive to the activity and selectivity of the reaction, and the effects have been investigated in detail.
- metal complex,
- olefin,
- epoxidation,
- hydrogen peroxide
1. [1]
  TAN Wei, SHA Lei, ZHAO Bao-Xiang. Chinese Journal of Synthetic Chemistry, 2003, 5:384-390 doi: 10.3969/j.issn.1005-1511.2003.05.005
2. [2]
  Krishnan K K, Thomas A M, Sindhu K S, et al. Tetrahedron., 2016, 72(1):1-16 doi: 10.1016/j.tet.2015.11.003
3. [3]
  Najafpour M M, Rahimi F, Amini M, et al. J. Chem. Soc. Dalton Trans., 2012, 41(36):11026-11031 doi: 10.1039/c2dt30553d
4. [4]
  Choudhary V R, Jha R, Jana P. Catal. Commun., 2008, 10(2):205-207
5. [5]
  Wang Y, Zhang Q, Shishido T, et al. J. Catal., 2002, 209(1):186-196
6. [6]
  Zhang J, Jiang P, Shen Y R, et al. J. Porous Mater., 2016, 23(2):431-440 doi: 10.1007/s10934-015-0097-4
7. [7]
  Yamaguchi K, Ebitani K, Kaneda K. J. Org. Chem., 1999, 64(8):2966-2968 doi: 10.1021/jo982347e
8. [8]
  Honma T, Nakajo M, Mizugaki T, et al. Tetrahedron Lett., 2002, 43:6229-6232 doi: 10.1016/S0040-4039(02)01296-0
9. [9]
  Mizuno N, Nozaki C, Kiyoto I, et al. J. Am Chem. Soc., 1998, 120(36):9267-9272 doi: 10.1021/ja980006c
10. [10]
  Li S, Zhang B, Kuehn F E. J. Org. Chem., 2013, 73:132-136
11. [11]
  Mgerlein W, Dreisbach C, Hugl H, et al. Catal. Today, 2007, 121:140-150 doi: 10.1016/j.cattod.2006.11.024
12. [12]
  Tse M K, Klawonn M, Bhor S, et al. Org. Lett., 2005, 36(31):987-990
13. [13]
  Qi J Y, Qiu L Q, Lam K H, et al. Chem. Commun., 2003, 34(9):1058-1059
14. [14]
  Ujwaldev S M, Sindhu K S, Thankachan A P, et al. Tetrahedron, 2016, 72(41):6175-6190 doi: 10.1016/j.tet.2016.08.052
15. [15]
  Zima A M, Lyakin O Y, Ottenbacher R V, et al. ACS Catal., 2016, 7:60-69
16. [16]
  Kueck J W, Anneser M R, Hofmann B, et al. ChemSuschem, 2015, 8(23):4056-4063 doi: 10.1002/cssc.201500930
17. [17]
  Hasan K, Brown N, Kozak C M. Green Chem., 2011, 42(37):1230-1237
18. [18]
  Anilkumar G, Bitterlich B, Gelalcha F G, et al. Chem. Commun., 2007, 38(19):289-291
19. [19]
  Dubois G, Murphy A, Stack T D P. Org. Lett., 2003, 5(14):2469-2472 doi: 10.1021/ol0347085
20. [20]
  Zheng W, Tan R, Zhao L, et al. RSC Adv., 2014, 4(23):11732-11739 doi: 10.1039/c3ra47183g
21. [21]
  Dai W, Li J, Li G, et al. Org. Lett., 2013, 15(16):4138-4141 doi: 10.1021/ol401812h
22. [22]
  Bagherzadeh M, Latifi R, Tahsini L. J. Mol. Catal. A:Chem., 2006, 260(1):163-169
23. [23]
  Lane B S, Burgess K C. J. Am. Chem. Soc., 2001, 123(12):2933-2934 doi: 10.1021/ja004000a
24. [24]
  Krishnan K K, Thomas A M, Sindhu K S, et al. Tetrahedron, 2016, 72(1):1-16 doi: 10.1016/j.tet.2015.11.003
25. [25]
  Shoji O, Fujishiro T, Nishio K. Catal. Sci. Technol., 2016, 16(5):5806-5811
26. [26]
  Stokes B J, Opra S M, Sigman M S. J. Am. Chem. Soc., 2012, 134(28):11408-11411 doi: 10.1021/ja305403s
27. [27]
  Méou A, Garcia M A, Brun P. J. Mol. Catal. A:Chem., 1999, 138(2/3):221-226
28. [28]
  ZHOU Zhi-Ming, LI Lian-Qiao, XU Qiao, et al. Chin. J. Org. Chem., 2005, 25:347-354 doi: 10.3321/j.issn:0253-2786.2005.04.001
29. [29]
  Buschmann H, Scharf H D, Hoffmann N, et al. Angew. Chem. Int. Ed., 1991, 30(5):477-515 doi: 10.1002/(ISSN)1521-3773
30. [30]
  Meunier B, de Visser S P. Chem. Rev., 2004, 104(9):3947-3980 doi: 10.1021/cr020443g
31. [31]
  Srinivasan K, Michaud P, Kochi J K. J. Am. Chem. Soc., 1986, 108(9):2309-2320 doi: 10.1021/ja00269a029
32. [32]
  Gamez P, Arends I, Reedijk J, et al. Chem. Commun., 2003, 19:2414-2415
33. [33]
  Grigoropoulou G, Clark J H, Elings J A. Green Chem., 2003, 5(1):1-7
34. [34]
  Bach R D, Canepa C, Winter J E, et al. J. Org. Chem., 1997, 62(15):5191-5197 doi: 10.1021/jo950930e
35. [35]
  Bjrkling F, Godtfredsen S, Kirk O. Chem. Commun., 1990, 19:1301-1303
36. [36]
  Chen K, Costas M, Kim J H, et al. J. Am. Chem. Soc., 2002, 124, 3026-3035 doi: 10.1021/ja0120025
37. [37]
  Kim C, Chen K, Kim J H, et al. J. Am. Chem. Soc., 1997, 119:5964-5965 doi: 10.1021/ja9642572
38. [38]
  Lim M H, Rohde J U, Stubna A, et al. Proc. Natl. Acad. Sci. U.S.A., 2003, 100:3665-3670 doi: 10.1073/pnas.0636830100
39. [39]
  Mas-Ballesté R, Que L. J. Am. Chem. Soc., 2007, 129(51):15964-15972 doi: 10.1021/ja075115i
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