ACCOUNT

Platinum-Catalyzed the Rearrangement of Propargylic Esters and C—H Bond Functionalization Adjacent to the Nitrogen of Tertiary Amines

  • Xia Xiaofeng ,
  • Li Lianhua ,
  • Liang Yongmin
Expand
  • State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000

Received date: 2013-01-09

  Revised date: 2013-02-01

  Online published: 2013-02-18

Supported by

Project supported by the National Natural Science Foundation of China (No. 21072080).

Abstract

Our recent progress in platinum-catalyzed the rearrangement of propargylic esters and C—H bond functionalization adjacent to the nitrogen of tertiary amines is summaried. The effect of the design of the substrates and additives on these reactions is described, and the mechanisms of these reactions are also discussed. At the same time, the first oxidant-free cross-dehydrogenative coupling (CDC) reaction under platinum-catalysis is proposed.

Cite this article

Xia Xiaofeng , Li Lianhua , Liang Yongmin . Platinum-Catalyzed the Rearrangement of Propargylic Esters and C—H Bond Functionalization Adjacent to the Nitrogen of Tertiary Amines[J]. Chinese Journal of Organic Chemistry, 2013 , 33(04) : 675 -686 . DOI: 10.6023/cjoc201301019

References

[1] (a) F黵stner, A. Chem. Soc. Rev. 2009, 38, 3208.
(b) Michelet, V.; Toullec, P. Y.; Gen閠, J.-P. Angew. Chem., Int. Ed. 2008, 47, 4268.
(c) F黵stner, A.; Davies, P.W. Angew. Chem., Int. Ed. 2007, 46, 3410.
(d) Marco-Contelles, J.; Soriano, E. Chem. Eur. J. 2007, 13, 1350.
(e) Zhang, L.; Sun, J.; Kozmin, S. A. Adv. Synth. Catal. 2006, 348, 2271.
(f) Nieto-Oberhuber, C.; L髉ez, S.; Jim閚ez-N?ñez, E.; Echavarren, A. M. Chem. Eur. J. 2006, 12, 5916.

[2] (a) Shu, X.-Z.; Yang, Y.-F.; Xia, X.-F.; Ji, K.-G.; Liu, X.-Y.; Liang, Y.-M. Org. Biomol. Chem., 2010, 8, 4077.
(b) Xia, X.-F.; Shu, X.-Z.; Ji, K.-G.; Yang, Y.-F.; Ali, S.; Liu, X.-Y.; Liang, Y.-M. J. Org. Chem. 2010, 75, 2893.
(c) Xia, X.-F.; Shu, X.-Z.; Ji, K.-G.; Ali, S.; Liu, X.-Y.; Liang, Y.-M. J. Org. Chem. 2011, 76, 342.

[3] (a) Li, G.; Zhang, G.; Zhang, L. J. Am. Chem. Soc. 2008, 130, 3740.
(b) Shi, X.; Gorin, D. J.; Toste, F. D. J. Am. Chem. Soc. 2005, 127, 5802.
(c) Amijs, C. H. M.; Lopez-Carrillo, V.; Echavarren, A. M. Org. Lett. 2007, 9, 4021.
(d) Blaszykowski, C.; Harrak, Y.; Goncalves, M.-H.; Cloarec, J.-M.; Dhimane, A.-L.; Fensterbank, L.; Malacria, M. Org. Lett. 2004, 6, 3771.

[4] Zheng, H.; Zheng, J.; Yu, B.; Chen, Q.; Wang, X.; He, Y.; Yang, Z.; She X. J. Am. Chem. Soc. 2010, 132, 1788.

[5] Ji, K.-G.; Shu, X.-Z.; Chen, J.; Zhao, S.-C.; Zheng, Z.-J.; Lu, L.; Liu, X.-Y.; Liang, Y.-M. Org. Lett. 2008, 10, 3919.

[6] Correa, A.; Marion, N.; Fensterbank, L.; Malacria, M.; Nolan, S. P.; Cavallo, L. Angew. Chem., Int. Ed. 2008, 47, 718.

[7] Spangler, C. W. Chem. Rev. 1976, 76, 187.

[8] (a) Odedra, A.; Datta, S.; Liu, R. S. J. Org. Chem. 2007, 72, 3289.
(b) Datta, S.; Odedra, A.; Liu, R. S. J. Am. Chem. Soc. 2005, 127, 11606.

[9] Shu, X.-Z.; Ji, K.-G.; Zhao, S.-C.; Zheng, Z.-J.; Chen, J.; Lu, L.; Liu, X.-Y.; Liang, Y.-M. Chem. Eur. J. 2008, 14, 10556.

[10] Xia, X.-F.; Song, X.-R.; Wang, N.; Wei, H.-L.; Liu, X.-Y.; Liang, Y.-M. RSC Adv. 2012, 2, 560.

[11] [11] Lu, L.; Liu, X.-Y.; Shu, X.-Z.; Yang, K.; Ji, K.-G.; Liang, Y.-M. J. Org. Chem. 2009, 74, 474.

[12] (a) Beak, P.; Lee, W.-K. J. Org. Chem. 1993, 58, 1109.
(b) Snieckus, V.; Cuevas, J.-C.; Sloan, C. P.; Liu, H.; Curran, D. P. J. Am. Chem. Soc. 1990, 112, 896.
(c) Suga, S.; Suzuki, S.; Yoshida, J. J. Am. Chem. Soc. 2002, 124, 30.
(d) Chatani, N.; Asaumi, T.; Ikeda, T.; Yorimitsu, S.; Ishii, Y.; Kakiuchi, F.; Murai, S. J. Am. Chem. Soc. 2000, 122, 12882.
(e) Chatani, N.; Asaumi, T.; Yorimitsu, S.; Ikeda, T.; Kakiuchi, F.; Murai, S. J. Am. Chem. Soc. 2001, 123, 10935.
(f) Li, C.-J. Acc. Chem. Res. 2009, 42, 335.
(g) Li, C.-J. Chem. Rev. 2005, 105, 3095.

[13] Boess, E.; Schmitz, C.; Klussmann, M. J. Am. Chem. Soc. 2012, 134, 5317.
Outlines

/