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Chinese Journal of Organic Chemistry >

2013 , Vol. 33 >Issue 07: 1382 - 1394

DOI: https://doi.org/10.6023/cjoc201301020

Reviews

Research and Progress in Chiral Binuclear Catalyst of First Row Transition Metal and Corresponding Nonlinear Effect

  • Yang Yan ,
  • Wang Liying ,
  • Luo Jun ,
  • Zhu Yulin
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  • School of Chemistry and Enviroment, South China Normal University, Guangzhou 510006

Received date: 2013-01-09

  Revised date: 2013-02-06

  Online published: 2013-02-18

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Abstract

The study on chiral binuclear complexes of first row transition metal has been expended to correlated fields such as asymmetric catalysis, biomimetic, functional supramolecular material and medicine, and reaches a research hot point of vast attraction and potential. Contrasting with other traditional organic-metal catalysts, the chiral binuclear complexes which combine several chiral centers and cooperated binuclear often play preferable catalysis behavior in enantioselective reaction. This review covers the recent progress in chiral binuclear complexes of V, Ti, Mn, Fe, Co, Ni, Cu, Zn applied in asymmetric reactions involving asymmetric addition, kinetic resolution, selective oxidation, asymmetric polymerization, as well as the mechanistic investigations. Some studies on the nonlinear effect along with the dimer catalysts are also discussed. The challenges and perspectives are given at the end of this article.

Key words： chiral binuclear complexes; first row transition metal; asymmetric catalysis; nonlinear effect

Cite this article

Yang Yan , Wang Liying , Luo Jun , Zhu Yulin . Research and Progress in Chiral Binuclear Catalyst of First Row Transition Metal and Corresponding Nonlinear Effect[J]. Chinese Journal of Organic Chemistry, 2013 , 33(07) : 1382 -1394 . DOI: 10.6023/cjoc201301020

References

[1] Hino, T.; Matsumoto, Y.; Nagano, S.; Sugimoto, H.; Fukumori, Y.; Murata, T.; Iwata, S.; Shiro, Y. Science 2010, 330, 1666.
[2] Kureshy, R. I.; Khan, N. H.; Sayed, H. R. Tetrahedron: Asymmetry 2001, 12, 433.
[3] Gavrilova, A. L.; Bosnich, B. Chem. Rev. 2004, 104, 349.
[4] Robson, R. Dalton Trans. 2008, 5113.
[5] Thakur, S. S.; Chen, S. W.; Li, W. J.; Shin, C. K.; Kim, S. J.; Koo, Y. M.; Kim, G. J. J. Organomet. Chem. 2006, 691, 1862.
[6] Kureshy, R. I.; Das, A.; Khan, N. H.; Abdi, S. H. R.; Bajaj, H. C. ACS Catal. 2011, 1, 1529.
[7] Wu, Y.-L.; Yao, Z.-J.; Hu, T.-S. Modern Organic Synthesis Chemistry, Science Press, Beijing, 2006, pp. 162～164 (in Chinese). (吴毓林, 姚祝军, 胡泰山, 现代有机合成化学, 科学出版社, 北京, 2006, pp. 162～164.)
[8] Satyanarayana, T.; Abraham, S.; Kagan, H. B. Angew. Chem., Int. Ed. 2009, 48, 456.
[9] Finn, M. G.; Sharpless, K. B. J. Am. Chem. Soc. 1991, 113, 113.
[10] Noyori, R.; Suga, S.; Oka, H.; Kitamura, M. Chem. Rev. 2001, 1, 85.
[11] Sato, I.; Urabe, H.; Ishiguro, S.; Shibata, T.; Soai, K. Angew. Chem., Int. Ed. 2004, 42, 315.
[12] Zhang, Z. J.; Wan, B. S.; Chen, H. L. Chin. J. Org. Chem. 2003, 23, 636 (in Chinese). (张占金, 万伯顺, 陈惠麟, 有机化学, 2003, 23, 636.)
[13] Gao, Y. H.; Xu, L. W.; Xia, C. G. J. Mol. Catal. 2008, 22, 6 (in Chinese). (高月华, 徐利文, 夏春谷, 分子催化, 2008, 22, 6.)
[14] Arjmand, F.; Parveen, S.; Afzal, M.; Shahid, M. J. Photochem. Photobiol. B 2012, 114, 15.
[15] Howson, S. E.; Scott, P. Dalton Trans. 2011, 40, 10268.
[16] Pardo, E.; Ruiz-Garcia, R.; Lloret, F.; Faus, J.; Julve, M.; Journaux, Y.; Novak, M. A.; Delgado, F. S.; Ruiz-Perez, C. Chem. Eur. J. 2007, 13, 2054.
[17] Iglesias, A. L.; Aguirre, G.; Somanathan, R.; Parra-Hake, M. Polyhedron 2004, 23, 3051.
[18] Lou, B. Y.; Wei, Y. Q.; Lin, Q. CrystEngComm 2012, 14, 2040.
[19] Brunel, J. M. Chem. Rev. 2005, 105, 857.
[20] Belokon, Y. N.; Caveda-Cepas, S.; Green, B.; Ikonnikov, N. S.; Khru-stalev, V. N.; Larichev, V. S.; Moscalenko, M. A.; North, M.; Orizu, C. Tararov, V. I.; Asinazzo, M. T.; Timofeeva G. I.; Yashkina, L. V. J. Am. Chem. Soc. 1999, 121, 3968.
[21] Belokon, Y. N.; Gutnov, A. V.; Moskalenko, M. A.; Yashkina, L. V.; Lesovoy, D. E.; Nicolai S. Ikonnikov, N. S.; Laricheva, V. S.; North, M. Chem. Commun. 2002, 244.
[22] Belokon, Y. N.; Blacker, A. J.; Carta, P.; Clutterbuck, L. A.; North, M. Tetrahedron 2004, 60, 10433.
[23] Zhang, Z. P.; Wang, Z.; Zhang, R. Z.; Ding, K. L. Angew. Chem. 2010, 122, 6898.
[24] Palomo, C.; Oiarbide, M.; Laso, A. Eur. J. Org. Chem. 2007, 2561.
[25] Bandini, M.; Piccinelli, F.; Tommasi, S.; Umani-Ronchi, A.; Ventrici, C. Chem. Commun. 2007, 616.
[26] Jammi, S.; Saha, P.; Sanyashi, S.; Sakthivel, S.; Punniyamurthy, T. Tetrahedron 2008, 64, 11724.
[27] Shi, Y.; Mao, Z. J.; Xue, Q. C.; Zhu, C. J.; Hu, H. W.; Cheng, Y. X. Inorg. Chem. Commun. 2012, 20, 259.
[28] Trost, B. M.; Yeh, V. S. C.; Ito, H.; Bremeyer, N. Org. Lett. 2002, 4, 2623.
[29] Trost, B. M.; Andrew, H.; Weiss, A. H.; von Wangelin, A. J. Am. Chem. Soc. 2006, 128, 8.
[30] Gommermann, N.; Knochel, P. Chem. Eur. J. 2006, 12, 4380.
[31] Gommermann, N.; Koradin, C.; Polborn, K.; Knochel, P. Angew. Chem., Int. Ed. 2003, 42, 5763.
[32] Muthupandi, P.; Alamsetti, S. K.; Sekar, G. Chem. Commun. 2009, 3288.
[33] Muthupandi, P.; Sekar, G. Org. Biomol. Chem. 2012, 10, 5347.
[34] Au-Yeung, T. L. L.; Chan, S. S.; Chan, A. S. C. Adv. Synth. Catal. 2003, 345, 537.
[35] Hanawa, H.; Uraguchi, D.; Konishi, S.; Hashimoto, T.; Maruoka, K. Chem. Eur. J. 2003, 9, 4405.
[36] Waltz, K. M.; Carroll, P. J.; Walsh, P. J. Organometallics 2004, 23, 127.
[37] Ay, S.; Ziegert, R. E.; Zhang, H.; Nieger, M.; Rissanen, K.; Fink, K.; Kubas, A.; Gschwind, R. M.; Brase, S. J. Am. Chem. Soc. 2010, 132, 12899.
[38] Lauterwasser, F.; Vanderheiden, S.; Brase, S. Adv. Synth. Catal. 2006, 348, 443.
[39] Chen, Z. H.; Yakura, K.; Matsunaga, S.; Shibasaki, M. Org. Lett. 2008, 10, 3239.
[40] Kato, Y.; Furutachi, M.; Chen, Z.; Mitsunuma, H.; Matsunaga, S.; Shibasaki, M. J. Am. Chem. Soc. 2009, 131, 9168.
[41] Mouri, S.; Chen, Z.; Mitsunuma, H.; Furutachi, M.; Matsunaga, S.; Shibasaki, M. J. Am. Chem. Soc. 2010, 132, 1255.
[42] Mouri, S.; Chen, Z.; Matsunaga, S.; Shibashi, M. Heterocycles 2012, 84, 879.
[43] Gopinath, P.; Watanabe, T.; Shibasaki, M. Org. Lett. 2012, 14, 1358.
[44] Xu, Y. J.; Matsunaga, S.; Shibasaki, M. Org. Lett. 2010, 12, 3246.
[45] Wezenberg, S. J.; Salassa, G.; Escudero-Adán, E. C.; Benet-Buchholz, J.; Kleij, A. W. Angew. Chem., Int. Ed. 2011, 50, 713.
[46] Escárcega-Bobadilla, M. V.; Anselmo, D.; Wezenberg, S. J.; Escudero-Adán, E. C.; Belmonte, M. M.; Martina, E.; Kleij, A. W. Dalton Trans. 2012, 41, 9766.
[47] Cozzi, P. G. Chem. Soc. Rev. 2004, 33, 410.
[48] Wezenberg, S. J.; Kleij, A. W. Adv. Synth. Catal. 2010, 352, 85.
[49] Zheng, X. L.; Jones, C. W.; Weck, M. Adv. Synth. Catal. 2008, 350, 255.
[50] Venkatasubbaiah, K.; Gill, C. S.; Takatani, T.; Sherrill, C. D.; Jones, C. W. Chem. Eur. J. 2009, 15, 3951.
[51] Sadhukhan, A.; Khan, N. H.; Roy, T.; Kureshy, R. I.; Abdi, S. H. R.; Bajaj, H. C. Chem. Eur. J. 2012, 18, 5256.
[52] Haak, R. M.; Castilla, A. M.; Belmonte, M. M.; Escudero-Adán, E. C.; Benet-Buchholz, J.; Kleij, A. W. Dalton Trans. 2011, 40, 3352
[53] Haak, R. M.; Belmonte, M.; Escudero-Adán, E. C.; Benet-Buchholz, J.; Kleij, A. W. Dalton Trans. 2010, 39, 593.
[54] Chen, S. W.; Kawthekar, R. B.; Kim, G. J. Tetrahedron Lett. 2007, 48, 297.
[55] Jin, L.; Huang, Y.; Jing, H.; Chang, T.; Yan, P. Tetrahedron: Asymmetry 2008, 19, 1947.
[56] Dro, C.; Bellemin-Laponnaz, S.; Welter, R.; Gade, L. H. Angew. Chem., Int. Ed. 2004, 43, 4479.
[57] Foltz, C.; Stecker, B.; Marconi, G.; Wadepohl, H.; Bellemin-La-ponnaz, S.; Gade, L. H. Chem. Commun. 2005, 5115.
[58] Kalow, J. A.; Doyle, A. G. J. Am. Chem. Soc. 2010, 132, 3268.
[59] Kalow, J. A.; Doyle, A. G. J. Am. Chem. Soc. 2011, 133, 16001.
[60] Ballistreri, F. P.; Brinchi, L.; Germani, R.; Savelli, G.; Tomaselli, G. A.; Toscano, R. M. Tetrahedron 2008, 64, 10239.
[61] Sun, Y.; Tang, N.; Liu, X. W.; Liu, W. S. Chin. Chem. Lett. 2004, 15, 973.
[62] Chen, L. H.; Cheng, F. X.; Jia, L.; Zhang, A. J.; Wu, J. C.; Tang, N. Chirality 2011, 23, 69.
[63] Patel, M. J.; Trivedi, B. M. Appl. Organomet. Chem. 2006, 20, 521.
[64] Romakh, V. B.; Therrien, B.; Süss-Fink, G.; Shulpin, G. B. Inorg. Chem. 2007, 46, 1315.
[65] Yeung, H. L.; Sham, K. C.; Tsang, C. S.; Lau, T. C.; Kwong, H. L. Chem. Commun. 2008, 3801.
[66] Sham, K. C.; Yeung, H. L.; Yiu, S. M.; Lau, T. C.; Kwong, H. L. Dalton Trans. 2010, 39, 9469.
[67] Rich, J.; Rodríguez, M.; Romero, I.; Vaquer, L.; Sala, X.; Llobet, M.; Corbella, M.; Collombe, M.; Fontrodona, X. Dalton Trans. 2009, 8117.
[68] Legros, J.; Bolm, C. Chem. Eur. J. 2005, 11, 1086.
[69] Costas, M.; Chen, K.; Que, L. Coord. Chem. Rev. 2000, 200.
[70] Takizawa, S.; Katayama, T.; Kameyama, C.; Onitsuka, K.; SuzuKi, T.; Yanagida, T.; Kawa, T.; Sasai, H. Chem. Commun. 2008, 1810.
[71] Takizawa, S.; Arteaga, F. A.; Yoshida, Y.; Kodera, J.; Nagata, Y.; Sasai, H. Dalton Trans. 2013, DOI: 10.1039/c2dt32202a in press.
[72] Mutti, F. G.; Gullotti, M.; Casella, L.; Santagostini, L.; Pagliarin, R.; Andersson, K. K.; Iozzie, M. F.; Zoppellaro, G. Dalton Trans. 2011, 40, 5436.
[73] Champouret, Y. D. M.; Nodes, W. J.; Scrimshire, J. A.; Singh, K.; Solan, G. A.; Young, I. Dalton Trans. 2007, 4565.
[74] Nakano, K.; Nozaki, K.; Hiyama, T. J. Am. Chem. Soc. 2003, 125, 5501.
[75] Nakano, K.; Hiyama, T.; Nozaki, K. Chem. Commun. 2005, 1871.
[76] Nakano, K.; Hashimotoa, S.; Nozaki, K. Chem. Sci. 2010, 1, 369.
[77] Noda, S.; Nakamura, A.; Kochi, T.; Chung, L. W.; Morokuma, K.; Nozaki, K. J. Am. Chem. Soc. 2009, 131, 14088.
[78] Cohen, C. T.; Coates, G. W. J. Polym. Sci., Part A: Polym. Chem. 2006, 44, 5182.
[79] Thomas, R. M.; Widger, P. C. B.; Ahmed, S. M.; Jeske, R. C.; Hirahata, W.; Lobkovsky, E. B.; Coates, G. W. J. Am. Chem. Soc. 2010, 132, 16520.
[80] Hirahata, W.; Thomas, R. M.; Lobkovsky, E. B.; Coates, G. W. J. Am. Chem. Soc. 2008, 130, 17658.
[81] Otero, A.; Fernández-Baeza, J.; Sánchez-Barba, L. J.; Tejeda, J.; Honrado, M.; Garcés, A.; Lara-Saánchez, A.; Rodréguez, A. M. Organometallics 2012, 31, 4191.
[82] Iglesias, A. L.; Aguirre, G.; Somanathan, R.; Parra-Hake, M. Polyhedron 2004, 23, 3051.
[83] Gao, J.; Woolleya, F. R.; Zingaro, R. A. Org. Biomol. Chem. 2005, 3, 2126
[84] Zhu, S. F.; Xu, B.; Wang, G. P.; Zhou, Q. L. J. Am. Chem. Soc. 2012, 134, 436.
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