Reviews

Progress in Transition Metal-Catalyzed Reactions of Oximes and Their Derivatives

  • Ran Longfei ,
  • Liang Hao ,
  • Guan Zhenghui
Expand
  • Key Laboratory of Synthetic and Natural Functional Molecule Chemistry of Ministry of Education, Department of Chemistry & Materials Science, Northwest University, Xi'an 710069

Received date: 2012-06-09

  Revised date: 2012-08-29

  Online published: 2012-09-10

Supported by

Project supported by the National Natural Science Foundation of China (Nos. 21272183, 21002077), the Fund of New Scientific Stars of Shanxi Province (No. 2012KJXX-26) and the Fund of Education Department of Shaanxi Provincial Government (No. 12JK0611).

Abstract

The recent progress in transition metal-catalyzed reactions of oximes and their derivatives is reviewed in this paper. The reactions mainly based on reductive acylation, catalyzed coupling, amination, and cyclization of oximes and their derivatives.

Cite this article

Ran Longfei , Liang Hao , Guan Zhenghui . Progress in Transition Metal-Catalyzed Reactions of Oximes and Their Derivatives[J]. Chinese Journal of Organic Chemistry, 2013 , 33(01) : 66 -75 . DOI: 10.6023/cjoc201206011

References

[1] (a) Boar, R. B.; McGhie, J. F.; Robinson, M.; Barton, D. H. R.; Horwell, D. C.; Stick, R. V. J. Chem. Soc., Perkin Trans. 1 1975, 1237.

(b) Boar, R. B.; McGhie, J. F.; Robinson, M.; Barton, D. H. R. J. Chem. Soc., Perkin Trans. 1 1975, 1242.

[2] Barton, D. H. R.; Zard, S. Z. J. Chem. Soc., Perkin Trans. 1 1985, 2191.

[3] Burk, M. J.; Casy, G.; Johnson, N. B. J. Org. Chem. 1998, 63, 6084.

[4] Zhu, G.; Casalnuovo, A. L.; Zhang, X. J. Org. Chem. 1998, 63, 8100.

[5] Zhao, H.; Vandenbossche, C. P.; Koenig, S. G.; Singh, S. P.; Bakale, R. P. Org. Lett. 2008, 10, 505.

[6] Guan, Z.-H.; Huang, K.; Yu, S.; Zhang, X. Org. Lett. 2009, 11, 481.

[7] Tang, W.; Capacci, A.; Sarvestani, M.; Wei, X.; Yee, N. K.; Senanayake, C. H. J. Org. Chem. 2009, 74, 9528.

[8] Guan, Z.-H.; Zhang, Z.-Y.; Ren, Z.-H.; Wang, Y.-Y.; Zhang, X. J. Org. Chem. 2011, 76, 339.

[9] Coffen, D. L.; Schaer, B.; Bizzarro, F. T.; Chung, J. B. J. Org. Chem. 1984, 49, 296.

[10] Prithwiraj, D.; Nonappa; Pandurangan, K.; Maitra, U.; Wailes, S. Org. Lett. 2007, 9, 2767.

[11] Udd, S.; Jokela, R.; Franzén, R.; Tois, J. Tetrahedron Lett. 2006, 47, 8247.

[12] Maimone, T. J.; Buchwald, S. L. J. Am. Chem. Soc. 2010, 132, 9990.

[13] Liu, S.; Yu, Y.; Liebeskind, L. S. Org. Lett. 2007, 9, 1947.

[14] Liu, S.; Liebeskind, L. S. J. Am. Chem. Soc. 2008, 130, 6918.

[15] Feng, X.-H.; Zhang, G.-Z.; Chen, C.-Q.; Yang, M.-Y.; Xu, X.-Y.; Huang, G.-S. Synth. Commun. 2009, 39, 1768.

[16] Ali, A.; Meyer, A. G.; Tuck, K. L. Synlett 2009, 955.

[17] Wang, L.; Huang, C.; Cai, C. Catal. Commun. 2010, 532.

[18] Ren, Z.-H.; Zhang, Z.-Y.; Yang, B.-Q.; Wang, Y.-Y.; Guan, Z.-H. Org. Let. 2011, 13, 5394.

[19] Tsutsui, H.; Narasaka, K. Chem. Lett. 1999, 45.

[20] Tsutsui, H.; Narasaka, K. Chem. Lett. 2001, 526.

[21] Zaman, S.; Kitamura, M.; Abell, A. D. Org. Lett. 2005, 7, 609.

[22] Kamijo, S.; Yamamoto, Y. Chem.-Asian J. 2007, 2, 568.

[23] (a) Narasaka, K.; Kitamura, M. Eur. J. Org. Chem. 2005, 7, 4505.

(b) Narasaka, K. Pure Appl. Chem. 2002, 74, 143.

(c) Kitamura, M.; Zaman, S.; Narasaka, K. Synlett 2001, 974.

[24] Tan, Y.; Hartwig, J. F. J. Am. Chem. Soc. 2010, 132, 3676.

[25] Chiba, S.; Zhang, L.; Sanjaya, S.; Ang, G. Y. Tetrahedron 2010, 66, 5692.

[26] Faulkner, A.; Bower, J. F. Angew. Chem., Int. Ed. 2012, 51, 1675.

[27] Parthasarathy, K.; Jeganmohan, M.; Cheng, C.-H. Org. Lett. 2008, 8, 325.

[28] Parthasarathy, K.; Cheng, C.-H. J. Org. Chem. 2009, 74, 9359.

[29] Zhang, X.; Chen, D.; Zhao, M.; Zhao, J.; Jia, A.; Li, X. Adv. Synth. Catal. 2011, 353, 719.

[30] Martin, R. M.; Bergman, R. G.; Ellman, J. A.; J. Org. Chem. 2012, 77, 2501.

[31] Too, P. C.; Wang, Y.-F.; Chiba, S. Org. Lett. 2010, 12, 5688.

[32] (a) Patureau, F. W.; Glorius, F. Angew. Chem., Int. Ed. 2011, 50, 1977.

(b) Guimond, N.; Gorelsky, S. I.; Fagnou, K. J. Am. Chem. Soc. 2011, 133, 6449.

(c) Rakshit, S.; Grohmann, C.; Besset, T.; Glorius, F. J. Am. Chem. Soc. 2011, 133, 2350.

(d) Guimond, N.; Gouliaras, C.; Fagnou, K. J. Am. Chem. Soc. 2010, 132, 6908.

[33] Too, P. C.; Chua, S. H.; Wong, S. H.; Chiba, S. J. Org. Chem. 2011, 76, 6159.

[34] Too, P. C.; Noji, T.; Lim, Y. J.; Li, X.; Chiba, S. Synlett 2011, 2789.

[35] Hyster, T. K.; Rovis, T. Chem. Commun. 2011, 47, 11846.

[36] (a) Sukhorukov, A. Y.; Ioffe, S. L. Chem. Rev. 2011, 111, 5004.

(b) Alonso, D. A.; Nájera, C. Chem. Soc. Rev. 2010, 39, 2891.

(c) Song, G.; Wang, F.; Li, X. Chem. Soc. Rev. 2012, 41, 3651.

(d) Chinnagolla, R. K.; Pimparkar, S.; Jeganmohan, M. Org. Lett. 2012, 14, 3032.

Outlines

/