SIOC English
有机化学
高级检索

有机化学 >

2012 , Vol. 32 >Issue 11: 2162 - 2165

DOI: https://doi.org/10.6023/cjoc201206012

研究简报

高立体、区域选择性合成(Z)-1-芳硫基-2-芳硒基烯

  • 谭平 ,
  • 李宁波 ,
  • 许新华
展开
  • a 湖南机电职业技术学院生物与化学工程系 长沙 410151;
    b 湖南大学化学化工学院 长沙 410082

收稿日期: 2012-06-10

  修回日期: 2012-07-13

  网络出版日期: 2012-07-19

基金资助

国家自然科学基金(No. 21172061)资助项目.

收起

Highly Regio- and Stereo-selective Synthesis of (Z)-1-Arylthio-2-Arylseleno Alkenes

  • Tan Ping ,
  • Li Ningbo ,
  • Xu Xinhua
Expand
  • a Department of Biological and Chemical Engineering, Hunan Mechanical and Electrical Polytechnic, Changsha 410151;
    b College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082

Received date: 2012-06-10

  Revised date: 2012-07-13

  Online published: 2012-07-19

Supported by

Project supported by the National Natural Science Foundation of China (No. 21172061).

Fold

摘要

氢氧化铯催化下, 四氢呋喃作溶剂, 室温、氮气保护下, 炔基硫醚与硒酚发生亲核加成反应, 立体选择性合成一系列(Z)-1-芳硫基-2-芳硒基烯, 收率70%～93%. 反应机理为氢氧化铯与硒酚反应产生的芳硒化铯, 随后对炔硫醚进行亲核加成, 形成的烯基负离子水解得到产物.

关键词： 亲核加成; 立体选择性性; 炔基硫醚; 氢氧化铯; (Z)-1-芳硫基-2-芳硒基烯

本文引用格式

谭平 , 李宁波 , 许新华 . 高立体、区域选择性合成(Z)-1-芳硫基-2-芳硒基烯[J]. 有机化学, 2012 , 32(11) : 2162 -2165 . DOI: 10.6023/cjoc201206012

Abstract

In the presence of catalytic amount of cesium hydroxide, the nucleophilic addition reaction of selenols to alkyne sulfurnides occurred in tetrahydrofuran at room temperature under nitrogen atmosphere to give highly regio- and stereo-selective (Z)-1-arylthio-2-arylseleno alkenes in 70%～93% yields. The mechanism involved the formation of cesium arylselenides and the nucleophilic addition to the alkynyl sulfides in the presence of cesium hydroxide. The corresponding alkenes were obtained upon hydrolysis.

Key words： nucleophilic addition; regioselectivity; alkynyl thioether; cesium hydroxide; (Z)-1-arylthio-2-arylseleno alkenes

参考文献

[1] Kuniyasu, H.; Ogawa, A.; Miyazaki, S. I.; Ryu, I.; Kambe, N.; Sonoda, N. J. Am. Chem. Soc. 1991, 113, 9796.

[2] Moro, A. V.; Nogueira, C. W.; Barbosa, N. B. V. J. Org. Chem. 2005, 70, 5257.

[3] Ogawa, A.; Ikeda, T.; Kimura, K.; Hirao, T. J. Am. Chem. Soc. 1999, 121, 5108.

[4] Ananikov, V. P.; Beletskaya, I. P.; Aleksandrov, G. G.; Eremenko, I. L. Organometallics 2003, 22, 1414.

[5] Ogawa, A.; Kuniyasu, H.; Sonoda, N.; Hirao, T. J. Org. Chem. 1997, 62, 8361.

[6] Cai, M. Z.; Wang, Y. G.; Hao, W. Y. Green Chem. 2007, 9, 1180.

[7] Li, J. Y.; Liu, J.; Cai, M. Z. J. Chem. Res. 2009, 10, 616.

[8] Ananikov, V. P.; Kabeshov, M. A.; Beletskaya, I. P. J. Organomet. Chem. 2003, 687, 451.

[9] Ananikov, V. P.; Kabeshov, M. A.; Beletskaya, I. P. Synlett 2005, 1015.

[10] Ananikov, V. P.; Beletskaya, I. P. Org. Biomol. Chem. 2004, 2, 284.

[11] Ananikov, V. P.; Kabeshov, M. A.; Beletskaya, I. P. Organometallics 2005, 24, 1275.

[12] Usugi, S. I.; Yorimitsu, H.; Shinokubo, H.; Oshima, K. Org. Lett. 2004, 6, 601.

[13] Dabdoub, M. J.; Jr. Guerrero, P. J. Tetrahedron Lett. 2001, 42, 7167.

[14] Watanabe, S. I.; Mori, E.; Nagai, H.; Iwamura, T.; Iwama, T.; Kataoka, T. J. Org. Chem. 2000, 65, 8893
[15] Huang, X.; Xu, X. H.; Zheng, W. X. Synth. Commun. 1999, 29, 2399.

[16] Zeng, J. C.; Lu, R. L.; Xu, X. H.; Fang, J. K.; Zhou, B.; Zhang, Q. L. Chin. J. Org. Chem. 2004, 24, 1482 (in Chinese).
(曾纪朝, 卢锐亮, 许新华, 方敬坤, 周冰, 张秋林, 有机化学, 2004, 24, 1482.)

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

[18] 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. 2009, 39. 2646.

[19] Li, X. W.; Liu, W. Q.; Zou, K. B.; Xu, X. H. Chin. J. Org. Chem. 2007, 27, 1176 (in Chinese).
(黎小武, 刘文奇, 邹康兵, 许新华, 有机化学, 2007, 27, 1176.)

[20] Schneider, C. C.; Godoi, B.; Prigol, M.; Nogueira, C. W.; Zeni, G. Organometallics 2007, 26, 4252.

[21] Perin, G.; Borges, E. L.; Alves, D. Tetrahedron Lett. 2012, 53, 2066.

[22] Ogawa, A.; Obayashi, R.; Ine, H.; Tsuboi, Y.; Sonoda, N.; Hirao, T. J. Org. Chem. 1998, 63, 881.

[23] Manarin, F.; Roehrs, J. A.; Prigol, M.; Alves, A.; Nogueira, C. W.; Zeni, G. Tetrahedron Lett. 2007, 48, 4805.

[24] Dabdoub, M. J.; Dabdoub, V. B.; Pereira, M. A. Tetrahedron Lett. 2001, 42, 1595.

[25] Tan, P.; Yin, X. H.; Yu, A. H.; Xu, X. H. Chin. J. Chem. 2011, 29, 765 (in Chinese).
(谭平, 尹显洪, 喻爱和, 许新华, 中国化学, 2011, 29, 765.)

[26] Cohen, R. J.; Fox, D. L.; Salvatore, R. N. J. Org. Chem. 2004, 69, 4265.

[27] Lothar, W. B.; Margarete, F. S.; Paulo, H. M. Tetrahedron Lett. 2004, 45(13), 2735.

[28] Guerrero, P. G.; Dabdoub, M. J.; Marques, F. A.; Wosch, C. L.; Baroni, A. C. M.; Ferreira, A. G. Synth. Commun. 2008, 38, 4379.

[29] Xia, X.; Zou, K. B.; Fang, D. W.; Xu, X. H. Chin. J. Org. Chem. 2008, 28, 1487 (in Chinese).
(夏湘, 邹康兵, 方大为, 许新华, 有机化学, 2008, 28, 1487.)
Options
文章导航

/

〈 〉