Report

Research Advances in the Synthetic Methods of Vinyl Bromides

  • Zhang Wensheng ,
  • Xu Wenjing ,
  • Kuang Chunxiang
Expand
  • a School of Technology, Jiaozuo Teachers College, Jiaozuo 454001;
    b Department of Chemistry, Tongji University, Shanghai 200092

Received date: 2013-10-09

  Revised date: 2013-11-06

  Online published: 2013-11-20

Supported by

Project supported by the National Natural Science Foundation of China (No. 21272174), the Foundation of He'nan Scientific and Technological Committee (Nos. 132300410206, 132300410167) and the Foundation of Jiaozuo Scientific and Technological Bureau (No. 2012017).

Abstract

Vinyl halides (1-halo-1-alkenes), especially vinyl bromides, represent a kind of organic synthetic blocks, which play important roles in the construction of polysubstituted alkenes through transition metal-catalyzed C—C cross-coupling reactions. Consequently, there have been much attentions in facile, efficient methods of preparing vinyl bromides. According to the types of the synthetic substrates used in the literatures, newly reported means on the synthesis of vinyl bromides in recent years are surveyed. The synthetic substrates involved in these new approaches include ketones, alkynes, propargylic alcohols, vinyl triflates, 3-aryl-2,3-dibromopropionic acids, benzyl bromides, acrylic acids, cyclopropenes and allylic alcohol derivatives, etc.

Cite this article

Zhang Wensheng , Xu Wenjing , Kuang Chunxiang . Research Advances in the Synthetic Methods of Vinyl Bromides[J]. Chinese Journal of Organic Chemistry, 2014 , 34(3) : 605 -609 . DOI: 10.6023/cjoc201310006

References

[1] Kutsumura, N.; Niwa, K.; Saito, T. Org. Lett. 2010, 12, 3316.

[2] (a) Poss, C. S.; Rychnovsky, S. D.; Schreiber, S. L. J. Am. Chem. Soc. 1993, 115, 3360.

(b) Paqutte, L. A.; Hofferberth, J. E. J. Org. Chem. 2003, 68, 2266.

[3] Yokota, M.; Toyota, M.; Ihara, M. Chem. Commun. 2003, 422.

[4] (a) Vanbrunt, M. P.; Ambenge, R. O.; Weinreb, S. M. J. Org. Chem. 2003, 68, 3323.

(b) Novikov, Y. Y.; Sampson, P. J. Org. Chem. 2005, 70, 10247.

[5] (a) Ohno, H.; Yamamoto, M.; Iuchi, M.; Tanaka, T. Angew. Chem., Int. Ed. 2005, 44, 5103.

(b) Miyamoto, H.; Okawa, Y.; Nakazaki, A.; Kobayashi, S. Tetrahedron Lett. 2007, 48, 1805.

(c) Suzuki, H.; Sakai, N.; Iwahara, R.; Fujiwara, T.; Satoh, M.; Kakehi, A.; Konakahara, T. J. Org. Chem. 2007, 72, 5878.

[6] (a) Takai, K.; Nitta, K.; Utimoto, K. J. Am. Chem. Soc. 1986, 108, 7408.

(b) Takai, K.; Ichiguchi, T.; Hikasa, S. Synlett 1999, 1268.

[7] (a) Naskar, D.; Roy, S. Tetrahedron 2000, 56, 1369.

(b) Das, J. P.; Roy, S. J. Org. Chem. 2002, 67, 7861.

(c) You, H.-W.; Lee, K.-J. Synlett 2001, 105.

[8] (a) Hirao, T.; Masunaga, T.; Ohshiro, Y.; Agawa, T. J. Org. Chem. 1981, 46, 3745.

(b) Abbas, S.; Hayes, C. J.; Worden, S. Tetrahedron Lett. 2000, 41, 3215.

(c) Kuang, C.; Senboku, H.; Tokuda, M. Tetrahedron 2002, 58, 1491.

(d) Horibe, H.; Kondo, K.; Okuno, H.; Aoyama, T. Synthesis 2004, 986.

[9] Spaggiari, A.; Vaccari, D.; Davoli, P.; Torre, G.; Prati, F. J. Org. Chem. 2007, 72, 2216.

[10] Gao, F.; Hoveyda, A. H. J. Am. Chem. Soc. 2010, 132, 10961.

[11] Chen, Z. W.; Li, J. H.; Jiang, H. F.; Zhu, S. F.; Li, Y. B.; Qi, C. R. Org. Lett. 2010, 12, 3262.

[12] Yao, M. L.; Quick, T. R.; Wu, Z. Z.; Quinn, M. P.; Kabalka, G. W. Org. Lett. 2009, 11, 2647.

[13] Zhang, W.-S.; Kuang, C.-X.; Su, C.-H. Chem. Reag. 2009, 31, 261 (in Chinese).

(张文生, 匡春香, 苏长会, 化学试剂, 2009, 31, 261.)

[14] Pawlu?, P.; Hreczycho, G.; Szudkowska, J.; Kubicki, M.; Marciniec, B. Org. Lett. 2009, 11, 3390.

[15] Yu, M.; Zhang, G. Z.; Zhang, L. M. Tetrahedron 2009, 65, 1846.

[16] Ye, L.; Zhang, L. Org. Lett. 2009, 11, 3646.

[17] Shen, X. Q.; Hyde, A. M.; Buchwald, S. L. J. Am. Chem. Soc. 2010, 132, 14076.

[18] Pan, J.; Wang, X.; Zhang, Y.; Buchwald, S. L. Org. Lett. 2011, 13, 4974.

[19] Imazaki, Y.; Shirakawa, E.; Ueno, R.; Hayashi, T. J. Am. Chem. Soc. 2012, 134, 14760.

[20] Zhang, W. S.; Kuang, C. X.; Yang, Q. Chin. J. Chem. 2009, 27, 1727.

[21] Kuang, C. X.; Senboku, H.; Tokuda, M. Tetrahedron Lett. 2001, 42, 3893.

[22] Bull, J. A.; Mousseau, J. J.; Charette, A. B. Org. Lett. 2008, 10, 5485.

[23] Li, W.; Li, J. C.; Wan, Z. K.; Wu, J. J.; Massefski, W. Org. Lett. 2007, 9, 4607.

[24] Wang, Y.; Lam, H. W. J. Org. Chem. 2009, 74, 1353.

[25] Yin, J. D.; Gallis, C. E.; Chisholm, J. D. J. Org. Chem. 2007, 72, 7054.

[26] Kutsumura, N.; Niwa, K.; Saito, T. Org. Lett. 2010, 12, 3316.

Outlines

/