REVIEW

Research Progress on Epoxidation of Olefins Catalyzed by Mn(II, III, V) in Different Valence States

  • Zou Xiaochuan ,
  • Shi Kaiyun ,
  • Li Jun ,
  • Wang Yue ,
  • Wang Cun ,
  • Deng Chaofang ,
  • Ren Yanrong ,
  • Tan Jun ,
  • Fu Xiangkai
Expand
  • a Department of Biological and Chemical Engineering, Chongqing University of Education, Nan'an 400067;
    b Key Laboratory of Applied Chemistry of Chongqing Municipality, Key Laboratory of Eco-environments in Three Gorges Reservoir Region Ministry of Education, Research Institute of Applied Chemistry, College of Chemistry and Chemical Engineering, Southwest University, Beibei 400715

Received date: 2016-04-05

  Revised date: 2016-05-03

  Online published: 2016-06-01

Supported by

Projects supported by the Basic and Frontier Research Project of Chongqing (Nos. cstc2015jcyjA0317, cstc2013jcyjA50033), the Scientific and Technological Research Program of Chongqing Municipal Education Commission (Nos. KJ1501411, KJ131513, KJ131512), the Innovation Team Building at Institutions of Higher Education in Chongqing (No. KJTD201325), the Key Laboratory of Green Synthesis and Analysis of Chongqing University of Education (No. 16xjpt08) and the Innovative Research Team in Chongqing University of Education (No. KYC-cxtd03-20141002).

Abstract

The epoxidation catalyzed by transition metals (Cr, Ni, Co, Ru, Mn) has been received widespread attention over the past decades, and the corresponding epoxides are widely used in the synthesis of pharmaceuticals, fine chemicals and pesticides. Compared to other transition metals, metal Mn catalyst has been widely used in organic synthesis due to its inexpensive, environment-friendly, chemical stability and high catalytic activity. This paper reviews the recent progress on epoxidation of olefins catalyzed by the catalysts which were formed by the reaction of different valence metal Mn(II, III, and V) and different NXOY ligands in different oxidants/co-catalyst systems. At the same time, the Mn catalysts with different valence states are involved in the process of the epoxidation of olefins and the mechanism of how to transfer the oxygen of reactive intermediates to the olefins was discussed.

Cite this article

Zou Xiaochuan , Shi Kaiyun , Li Jun , Wang Yue , Wang Cun , Deng Chaofang , Ren Yanrong , Tan Jun , Fu Xiangkai . Research Progress on Epoxidation of Olefins Catalyzed by Mn(II, III, V) in Different Valence States[J]. Chinese Journal of Organic Chemistry, 2016 , 36(8) : 1765 -1778 . DOI: 10.6023/cjoc201604010

References

[1] Liu, X.; Wang, F. Coord. Chem. Rev. 2010, 256, 1115.
[2] Limburg, B.; Bouwman, E.; Bonnet, S. Coord. Chem. Rev. 2012, 256, 1451.
[3] Talsi, E. P.; Bryliakov, K. P. Coord. Chem. Rev, 2012, 256, 1418.
[4] Monfared, H. H.; Ghorbanloo, M.; Aghapoor, V.; Mayer, P. Appl. Catal. A: Gen. 2010, 372, 209.
[5] Ballistreri, F. P.; Brinchi, L.; Germani, R.; Savelli, G.; Tomaselli, G. A.; Toscanoa, R. M. Tetrahedron 2008, 64, 10239.
[6] Wegermann, C. A.; Ribeiro, R. R.; Ucoski, G. M.; Nakagaki, S.; Nunes, F. S.; Drechsel1, S. M. Appl. Catal. A: Gen. 2014, 471, 56.
[7] Stamatis, A.; Vartzouma, C.; Louloudi, M. Catal. Commun. 2011, 12, 475.
[8] Bagherzadeh, M.; Latifi, R.; Tahsini, L. J. Mol. Catal. A: Chem. 2006, 260, 163.
[9] Amini, M.; Bagherzadeh, M. M.; Oradi, S. Z.; Boghaei, D. M.; Ellern, A.; Woo, L. K. J. Coord. Chem. 2013, 66, 464.
[10] Zhang, W.; Loebach, J. L.; Wilson, S. R.; Jacobsen, E. N. J Am Chem Soc. 1990, 112, 2801.
[11] Visser, S. P. D.; Sason, S. J. Am. Chem. Soc. 2003, 125, 7413.
[12] Xia, Q. H.; Ge, H. Q.; Ye, C. P.; Liu, Z. M.; Su, K. X. Chem. Rev. 2005, 105, 1603.
[13] Keerthi, K. K.; Thomas, A. M.; Sindhu, K. S.; Anilkumar, G. Tetrahedron 2016, 72, 1.
[14] Neu, H. M.; Baglia, R. A.; Goldberg, D. P. Acc. Chem. Res. 2015, 48, 2754.
[15] Chen, Z. Q.; Yin, G. C. Chem. Soc. Rev. 2015, 44, 1083.
[16] Chang, S.; Galvin, J. M.; Jacobsen, E. N. J. Am. Chem. Soc. 1994, 116, 6937.
[17] Choudary, B. M.; Chowdari, N. S.; Kantam, M. L.; Santhi, P. L. Catal. Lett. 2001, 76, 213.
[18] Sutra, P.; Brunel, D. Chem Commun. 1996, 2485.
[19] Angelino, M. D.; Laibinis, P. E. Macromolecules 1998, 31, 7581.
[20] Leadbeater, N. E.; Marco, M. Chem. Rev. 2002, 102, 3217.
[21] Sui, Y.; Fu, X. K.; Zeng, R. Q.; Ma, X. B. J. Mol. Catal. A: Chem. 2004, 217, 133.
[22] Bao, H. B.; Fu, X. K.; Bai, R. F.; Ren, W. S.; Tu, X. B. Chem. J. Chin. Univ. 2008, 25, 927 (in Chinese).
(包河彬, 傅相锴, 白若飞, 任文山, 涂小波, 高等学校化学学报, 2008, 25, 927.)
[23] Bai, R. F.; Fu, X. K.; Bao, H. B.; Ren, W. S. Catal. Commun. 2008, 9, 1588.
[24] Ren, W. S.; Fu, X. K.; Bao, H. B.; Bai, R. F.; Ding, P. P.; Sui, B. L. Catal. Commun. 2009, 10, 788.
[25] Ren, W. S.; Fu, X. K. J. Mol. Catal. A: Chem. 2009, 312, 4.
[26] Fu, D.; Fu, X. K.; Bao, H. B.; Ren, W. S. J. Mol. Catal. 2007, 4, 368 (in Chinese).
(富丹, 傅相锴, 包河彬, 任文山, 分子催化, 2007, 4, 368.)
[27] Shen, H. S.; Fu, X. K.; Bao, H. B.; Chen, J. X., Gong, B.W. Polym. Adv. Technol. 2009, 20, 77.
[28] Zou, X. C.; Chen, S. C.; Ren, Y. R.; Shi, K.Y., Li, J., Fu, X. K. Sci. China. Chem. 2012, 55, 2396.
[29] Tu, X. B.; Fu, X. K.; Hu, X. Y.; Li, Y. D. Inorg. Chem. Commun. 2010, 13, 404.
[30] Zou, X. C.; Shi, K. Y.; Chen, S. C.; Fu, X. K. Chem. J. Chin. Univ. 2013, 34, 2319 (in Chinese).
(邹晓川, 石开云, 陈绍成, 傅相锴, 高等学校化学学报, 2013, 34, 2319.)
[31] Gong, B. W.; Fu, X. K.; Chen, J. X.; Li, Y. D.; Zou, X. C.; Tu, X. B.; Ding, P. P.; Ma, L. P. J. Catal. 2009, 262, 9.
[32] Zou, X. C.; Fu, X. K.; Li, Y. D.; Tu, X. B.; Fu, S. D.; Luo, Y. F.; Wu, X. J. Adv. Synth. Catal. 2010, 352, 163.
[33] Zou, X. C.; Fu, X. K.; Luo, Y. F. Acta Chim. Sinica 2011, 69, 431 (in Chinese).
(邹晓川, 傅相锴, 罗云飞, 化学学报, 2011, 69, 431.)
[34] Zou, X. C.; Li, J.; Shi, K. Y.; Li, G. J.; Fu, X. K. Chin. J. Inorg. Chem. 2012, 28, 1031 (in Chinese).
(邹晓川, 李俊, 石开云, 李贵节, 傅相锴, 无机化学学报, 2012, 28, 1031.)
[35] Zou, X. C.; Shi, K. Y.; Wang, C. Chin. J. Catal. 2014, 35, 1446.
[36] Huang, J.; Fu, X. K.; Wang, G.; Li, C,; Hu X. Y. Dalton Trans. 2011, 40, 3631.
[37] Huang, J.; Fu, X. K.; Miao, Q. Catal. Sci. Technol. 2011, 1, 1472.
[38] Huang, J.; Fu, X. K.; Wang, G.; Miao, Q.; Wang, G. M. Dalton Trans. 2012, 41, 10661.
[39] Cai, J. L.; Huang, J.; Li, C. M.; Feng, H.; Liu, Z. G. RSC Adv. 2013, 3, 18661.
[40] Jia, Z. Y.; Fu, X. K.; Luo, Y. F.; Zhang, H. Z.; Huang, X. M.; Wu, H. J. Inorg. Organomet. Polym. Mater. 2012, 22, 415.
[41] Huang, X. M.; Fu, X. K.; Jia, Z. Y.; Miao, Q.; Wang, G. M. Catal. Sci. Technol. 2013, 3, 415.
[42] Huang, J.; Tang, M.; Li, X.; Zhong, G. Z.; Li, C. M. Dalton Trans. 2014, 43, 17500.
[43] Huang, J.; Tang, M.; Li, C. M. RSC Adv. 2014, 4, 46498.
[44] Kam, P. H.; Wing, L. W.; Kin, M. L.; Cheuk, P. L.; Tak, H. C.; Kwok, Y. W. Chem. Eur. J. 2008, 14, 7988.
[45] Qi, B.; Lou, L. L.; Yu, K.; Bian, W.; Liu, S. X. Catal. Commun. 2011, 15, 52.
[46] Zheng, W. G.; Tan, R.; Zhao, L. L.; Chen, Y. J.; Xiong, C. W.; Yin, D. H. RSC Adv. 2014, 4, 11732.
[47] Qi, J. Y.; Li, Y. M.; Zhou, Z. Y.; Che, C. M.; Yeung, C. H.; Chan, A. S. C. Adv. Synth. Catal. 2005, 347, 45.
[48] Dong, J. J.; Saisaha, P.; Meinds. T, G.; Alsters, P. L.; Ijpeij, E. G.; Van Summeren, R. P.; Mao, B.; Fananas, M. M.; de Boer, J. W.; Hage, R.; Feringa, B. L.; Browne, W. R. ACS Catal. 2012, 2, 1087.
[49] Rich, J.; Manrique, E.; Molton, F.; Duboc, C.; Marie, N. C.; Rodriguez, M.; Romero, I. Eur. J. Inorg. Chem. 2014, 2663.
[50] Stamatis, A.; Vartzouma, C.; Louloudi, M. Catal. Commun. 2011, 12, 475.
[51] Murphy, A.; Dubois, G.; Stack, T. D. P. J. Am. Chem. Soc. 2003, 125, 5250.
[52] Murphy, A.; Pace, A; Stack, T. D. P. Org. Lett. 2004, 6, 3119.
[53] Wu, M.; Wang, B.; Wang, S.; Xia, C.; Sun, W. Org. Lett. 2009, 11, 3622.
[54] Maity, N. C.; Bera, P. K.; Ghosh, D.; Abdi, S. H. R.; Kureshy, R. I.; Khan, N. U. H.; Bajaj, H. C.; Suresh, E. Catal. Sci. Technol. 2014, 4, 208.
[55] Wang, X.; Miao, C.; Wang, S.; Xia, C.; Sun, W. ChemCatChem 2013, 5, 2489.
[56] Ottenbacher, R. V.; Bryliakov, K. P.; Talsi, E. P. Adv. Synth. Catal. 2011, 353, 885.
[57] Dai,W.; Li, J.; Li, G. S.; Yang, H.; Wang, L. Y.; Gao, S. Org. Lett. 2013, 15, 4138.
[58] Dai,W.; Shang, S. S.; Chen, B.; Li, G. S.; Wang, L. Y.; Ren, L. H.; Gao, S. J. Org. Chem. 2014, 79, 6688.
[59] Hashihayata, T.; Ito, Y.; Katsuki, T. Tetrahedron 1997, 53, 9541.
[60] Saihu, L.; Benjamin, L. Angew. Chem., Int .Ed. 2010, 49, 628.
[61] Wu, M.; Wang, B.; Wang, S. F.; Xia, C. G.; Sun, W. Org. Lett. 2009, 11, 3622.
[62] Wang, B.; Miao, C. X.; Wang, S. F.; Xia, C. G.; Sun, W. Chem. Eur. J. 2012, 18, 6750.
[63] Wang, X.; Miao, C. X.; Wang, S. F.; Xia, C. G.; Sun, W. ChemCatchem 2013, 5, 2489.
[64] Shen, D. Y.; Miao, C. X.; Wang, S. F.; Xia, C. G.; Sun, W. Eur. J. Inorg. Chem. 2014, 33, 5777.
[65] Miao, C. X.; Wang, Bin.; Wang, Y.; Xia, C. G.; Lee,Y. M.; Nam, W.; Sun, W. J. Am. Chem. Soc. 2016, 138, 936.
[66] Shen, D. Y.; Qiu, B.; Xu, D. Q, Miao, C. X.; Xia, C. G.; Sun, W. Org. Lett. 2016, 18, 372.
[67] Bagherzadeh, M.; Latifi, R.; Tahsini, L. J. Mol. Catal. A: Chem. 2006, 260, 163.
[68] Zhong, S.; Tan, Y.; Fu, Z.; Xie, Q.; Xie, F.; Zhou, X.; Ye, Z.; Peng, G.; Yin, D. J. Catal. 2008, 256, 154.
[69] Ruffo, F.; Bismuto, A.; Carpentieri, A.; Cucciolito, M. E.; Lega, M. Inorg. Chim. Acta 2013, 405, 288.
[70] Amato, M. E.; Ballistreri, F. P.; Pappalardo, A.; Tomaselli, G. A.; Toscano, R. M.; Williams, D. J. Eur. J. Org. Chem. 2005, 3562.
[71] Suresh, P.; Srimurugan, S.; Dere, T. D.; Ragavan, R. V.; Gopinath, V. S. Tetrahedron: Asymmetry 2013, 24, 669.
[72] Erdem, O.; Guzel, B. Inorg. Chim. Acta 2014, 418, 153.
[73] Irie, R.; Noda, K.; Ito, Y.; Matsumoto, N.; Katsuki, T. Tetrahedron Lett. 1990, 31, 7345.
[74] Katsuki, T. Synlett 2003, 281.
[75] Chen, L. H.; Cheng, F. X.; Jia, L.; Zhang, A. J.; Wu, J. C.; Tang, N. Chirality 2011, 23, 69.
[76] Luo, R. C.; Tan, R.; Peng, Z. G.; Zhang, W. G.; Kong, Y.; Yin, D. H. J. Catal. 2012, 287, 170.
[77] Borriello, C.; Litto, R. D.; Panunzi, A.; Ruffo, F. Tetrahedron: Asymmetry 2004, 15, 681.
[78] Zhao, S. S.; Zhao, J. Q.; Zhao, D. M. Carbohydr. Res. 2007, 342, 254.
[79] Huang, X. M.; Fu, X. K.; Wu, X. J.; Jia, Z. Y. Tetrahedron Lett. 2013, 54, 4041.
[80] Solati, Z.; Hashemi, M.; Ebrahimi, L. Catal. Lett. 2011, 141, 163.
[81] Bendix, J.; Meyer, K.; Weyhermuller, T.; Bill, E.; Metzler-Nolte, N.; Wieghardt, K. Inorg. Chem. 1998, 37, 1767.
[82] Bosch, I. G.; Gómez, L.; Polo, A.; Ribas, X.; Costas, M. Adv. Synth. Catal. 2012, 354, 65.
[83] Lyakin, O.Y.; Ottenbacher, R. V.; Bryliakov, K. P.; Talsi, E. P. ACS Catal. 2012, 2, 1196.
[84] Ottenbacher, R. V.; Samsonenko, D. G. Talsi, E. P.; Bryliakov, K. P. ACS Catal. 2014, 4, 1599.
[85] Mcgarrigle, E. M.; Gilheany, D. G. Chem. Rev. 2005, 105, 1563
[86] Engelhardt, U.; Linker, T. Chem. Commun. 2005, 1152.
[87] Fu, H.; Look, G. C.; Zhang, W.; Jacobsen, E. N.; Wang, C. H. J. Org. Chem. 1991, 56, 6497.
[88] Norrby, P. O.; Linde, C.; kermark, B. J. Am. Chem. Soc. 1995, 117, 11035.
[89] Backvall, J. E.; Bokman, F.; Blomberg, M. R. A. J. Am. Chem. Soc. 1992, 114, 534.
[90] Adam, W.; Mock, K. C.; Saha, M. C. R.; Herderich, M. J. Am. Chem. Soc. 2000, 122, 9685.
[91] Adam, W.; Roschmann, K. J.; Saha, M. C. R.; Seebach, D. J. Am. Chem. Soc. 2002, 124, 5068.
[92] Luo, Y. F.; Zou, X. C.; Fu, X. K.; Huang, X. M.; Jia, Z. Y. Sci. China Chem. 2011, 41, 433 (in Chinese).
(罗云飞, 邹晓川, 傅相锴, 贾紫永, 黄雪梅, 中国科学(化学), 2011, 41, 433.)
[93] Fraile, J. M.; Garci, J. I.; Mayoral, J. A. Chem Rev. 2009, 109, 360.
[94] Sellner, H.; Kajalainen, J. K.; Seebach, D. Chem. Eur. J. 2001, 7, 2873.
[95] Paucki, M.; Pospisil, P. J.; Zhang, W.; Jacobsen, E. N. J. Am. Chem. Soc. 1994, 116, 9333.
[96] Kureshy, R. I.; Ahamd, I.; Khan, N. H.; Abdi, S. H. R.; Singh, S.; Pandia, P. H.; Jasram, R. V. J. Catal. 2005, 235, 28.
[97] Liu, Y. L.; Zhu, Y. P.; Li, M.; Yuan, Z. Y. Acta. Chim. Sinica 2014, 72, 521 (in Chinese).
(刘亚录, 朱运培 李敏, 袁忠勇, 化学学报, 2014, 72, 521.)
[98] Zeng, R. Q.; Fu, X. K.; Sui, Y. Chemistry 2006, 69, 814 (in Chinese).
(曾仁权, 傅相锴, 隋岩, 化学通报, 2006, 69, 814.)
[99] Jacobsen, E. N.; Zhang, W.; Muci, A. R.; Ecker, J. R.; Deng, L. J. Am. Chem. Soc. 1991, 113, 7063.
[100] Hosoya, N.; Hatayama, A.; Irie, R.; Sasaki, H.; Katsuki, T. Tetrahedron 1994, 50, 4311.
[101] Rao, C. N. R.; Natarajan, S.; Neeraj, S. J. Solid State Chem. 2000, 152, 302.
[102] Thomas, J. M.; Raja, R.; Sankar, G. Nature 1999, 398, 227.
[103] Wu, X. J.; Fu, X. K.; Huang, J.; Jia, Z. Y. Chin. J. Inorg. Chem. 2012, 28, 2341 (in Chinese).
(吴小菊, 傅相锴, 黄静, 贾紫永, 无机化学学报, 2012, 28, 2341.)

Outlines

/