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Chinese Journal of Organic Chemistry >

2013 , Vol. 33 >Issue 03: 558 - 561

DOI: https://doi.org/10.6023/cjoc201211028

Articles

Hydroselenation of Terminal Alkynes Catalyzed by Cesium Hydroxide: Highly Stereo- and Regio-selective Synthesis of (E)-1-Arylselenoalkenes

  • Wang Xiaoyong ,
  • Li Zhizhang ,
  • Zhang Weijun ,
  • Wang Xie ,
  • Chen Jinyang ,
  • Li Ningbo ,
  • Qiu Renhua ,
  • Xu Xinhua
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  • a Department of Life Science and Chemical Engineering, Hunan University of Science and Engineering, Yongzhou 425100;
    b College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082

Received date: 2012-11-15

  Revised date: 2012-12-11

  Online published: 2012-12-13

Supported by

Project supported by the Natural Science Foundation of Hunan Province (No. 11JJ2009) and the National Natural Science Foundation of China (No. 21273068).

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Abstract

In the presence of catalytic amount of cesium hydroxide, the hydroselenation of terminal alkynes occurred in N,N-dimethylformamide (DMF) at room temperature under nitrogen atmosphere to afford (E)-1-organseleno-1-alkene in high yields. The reaction mechanism is that selenols reacted with cesium hydroxide to give cesium selenides, which underwent nucleophilic addition to the alkynes to form selenium vinylic anion, hydrolyzed to give product (E)-1-organoselenovinylene and catalyst cesium hydroxide. The method could provide a new and expedient way for the hydroselenation of unactivated alkynes.

Key words： nucleophilic addition; regioselectivity; terminal alkyne; hydroselenolation; cesium hydroxide; (E)-1-organoseleno-1-alkene

Cite this article

Wang Xiaoyong , Li Zhizhang , Zhang Weijun , Wang Xie , Chen Jinyang , Li Ningbo , Qiu Renhua , Xu Xinhua . Hydroselenation of Terminal Alkynes Catalyzed by Cesium Hydroxide: Highly Stereo- and Regio-selective Synthesis of (E)-1-Arylselenoalkenes[J]. Chinese Journal of Organic Chemistry, 2013 , 33(03) : 558 -561 . DOI: 10.6023/cjoc201211028

References

[1] Beletskaya, I.; Moberg, C. Chem. Rev. 1999, 99, 3435.

[2] Bhadra, S.; Saha, A.; Ranu, B. C. J. Org. Chem. 2010, 75, 4864.

[3] Perin, G.; Lenardão, E. J.; Jacob, R. G.; Panatieri, R. B. Chem. Rev. 2009, 109, 1277.

[4] Braga, A. L.; Marchi, M. I.; Andrade, L. H.; Silveira, C. C. Synth. Commun. 2000, 30, 407.

[5] Knapton, D. J.; Meyer, T. Y. Org. Lett. 2004, 6, 687.

[6] Knapton, D. J.; Meyer, T. Y. J. Org. Chem. 2005, 70, 785.

[7] Huang, X.; Sun, A. J. Org. Chem. 2000, 65, 6561.

[8] Ranu, B. C.; Chattopadhyay, K.; Banerjee, S. J. Org. Chem. 2006, 71, 423.

[9] Zeng, J. C.; Lu, R. L.; Xu, X. H. Chin. J. Org. Chem. 2004, 24, 1482.

[10] Zou, K. B.; Qiu, R. H.; Fang, D. W.; Liu, X. Y.; Xu, X. H. Synth. Commun. 2008, 38, 2237.

[11] Liu, W. Q.; Yin, X. H.; Cai, X. T.; Zhang, Z. Y.; Li, R. X.; Chen, S. H.; Xu, X. H. Chin. J. Org. Chem. 2010, 30, 1066 (in Chinese).
(刘文奇, 尹显洪, 蔡喜田, 张尊英, 李若信, 陈四海, 许新华, 有机化学, 2010, 30, 1066.)

[12] Zhao B. T.; WuS. J.; Ye, B. X. Chin. J. Org. Chem. 2011, 31, 1027 (in Chinese).
(赵邦屯, 吴圣江, 冶保献, 有机化学, 2011, 31, 1027.)

[13] Zou, K. B.; Yin, X. H.; Liu, W. Q.; Qiu, R. H.; Li, L. X.; Shao, L. L.; Li, Y. H.; Xu, X. H.; Yang, R. H. Synth. Commun. 2008, 39, 2464.

[14] Petragnani, J. N.; Rodrigues, R.; Comasseto, V. J. Organomet. Chem. 1976, 114, 281.

[15] Huang, X.; Zhu, L. S. J. Chem. Soc., Perkin Trans. 1 1996, 767.

[16] Reich, H. J.; Willis, W. W.; Clark, P. D. J. Org. Chem. 1981, 46, 2775.

[17] Silveira, C. C.; Mendes, S. R.; Wolf, L.; Braz, J. Chem. Soc. 2010, 21, 2138.

[18] Saha, A.; Saha, D.; Ranu, B. C. Org. Biomol. Chem. 2009, 1652.

[19] Comasseto, J. V.; Ferreira, J. T. B.; Petragnani, N. J. Organomet. Chem. 1981, 216, 287.
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