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2013 , Vol. 33 >Issue 05: 1010 - 1014

DOI: https://doi.org/10.6023/cjoc201212030

研究论文

单质硒促进的格氏试剂自偶联反应

  • 唐金鹏 ,
  • 唐渝 ,
  • 杨骏 ,
  • 张渊明
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  • 暨南大学生科院化学系有机化学专业 广州 510632

收稿日期: 2012-12-20

  修回日期: 2013-01-19

  网络出版日期: 2013-01-23

基金资助

国家大学生创新(No. 101055920)资助项目.

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Selenium-Promoted Homocoupling of Grignard Reagents

  • Tang Jinpeng ,
  • Tang Yu ,
  • Yang Jun ,
  • Zhang Yuanming
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  • Department of Chemistry, College of Life Science and Technology, Jinan University, Guangzhou 510632

Received date: 2012-12-20

  Revised date: 2013-01-19

  Online published: 2013-01-23

Supported by

Project supported by the National University Student Innovative Program (No. 101055920).

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摘要

通过探讨镁屑和单质硒的量、催化剂及配体等对反应的影响, 获得制备对称偶联产物的较佳实验条件, 成功得到较高分离产率(65%～92%)的15个对称芳烃或烷烃偶联目标产物, 在实验结果基础上, 提出了硒可在反应中循环的合理机理.

关键词： 格氏试剂; 单质硒; 自偶联

本文引用格式

唐金鹏 , 唐渝 , 杨骏 , 张渊明 . 单质硒促进的格氏试剂自偶联反应[J]. 有机化学, 2013 , 33(05) : 1010 -1014 . DOI: 10.6023/cjoc201212030

Abstract

The optimized reacting conditions were obtained by exploring the amount of magnesium and selenium, and the influence of catalysts and ligands. 15 homo-coupling aromatic or aliphatic products were obtained in high isolated yields of 65%～92%. A reasonable mechanism of selenium cycling in reaction was proposed based on experimental results.

Key words： Grignard reagent; elemental selenium; homo-coupling

参考文献

[1] Hassan, J.; Sevignon, M.; Gozzi, C.; Schulz, E.; Lemaire, M. Chem. Rev. 2002, 102, 1359.
[2] Kiso, Y.; Yamamoto, K.; Tamao, K.; Kumada, M. J. Am. Chem. Soc. 1972, 94, 4373.
[3] Corriu, R. J. P.; Jmasse, J. P. J. Chem. Soc., Chem. Commun. 1972, 3, 144a.
[4] Terao, J.; Watanabe, H.; Ikumi, A.; Kuniyasu, H.; Kambe, N. J. Am. Chem. Soc. 2002, 124, 4222.
[5] Liu, T.-P.; Xie, J.-J.; Li, B.; Cai, L.-Z.; Tao, X.-C. Chin. J. Org. Chem. 2011, 31, 2173 (in Chinese).
(刘涛平, 谢俊杰, 李彬, 蔡良珍, 陶晓春, 有机化学, 2011, 31, 2173.)
[6] Zhang, G.-F.; Zhao, X.-B.; Ding, C.-R.; Liu, H.-J.; Liang, X.-M. Chin. J. Org. Chem. 2011, 31, 1736 (in Chinese).
(张国富, 赵晓宝, 丁成荣, 刘会君, 梁鑫淼, 有机化学, 2011, 31, 1736.)
[7] Zhang, Y.; Luo, S.; Zhu, C.-J. Chin. J. Org. Chem. 2012, 32, 2073 (in Chinese).
(张燕, 罗莎, 朱成建, 有机化学, 2012, 32, 2073.)
[8] Karimi, B.; Esfahan, F. K. Chem. Commun. 2011, 47, 10452.
[9] Raghu, D. N.; Choavarit, K.; Ekasith, S.; Karan, B.; Masahiro, E.; Sangita, K.; Hidehiro, S. J. Am. Chem. Soc. 2012, 134, 20250.
[10] Cahiez, G.; Chaboche, C.; Mahuteau-Betzer, F.; Mathieu, A. Org. Lett. 2009, 7, 1943.
[11] Lei, A.-W.; Srivastava, M.; Zhang, X.-M. J. Org. Chem. 2002, 67, 1969.
[12] Lei, A.-W.; Zhang, X.-M. Tetrahedron Lett. 2002, 43, 2525.
[13] Lei, A.-W.; Zhang, X.-M. Org. Lett. 2002, 4, 2285.
[14] Zhao, Y.-S.; Wang, H.-B.; Hou, X.-H.; Hu, Y.-H.; Lei, A.-W.; Zhang, H.; Zhu, L.-Z. J. Am. Chem. Soc. 2006, 128, 15048.
[15] Liu, W.; Lei, A.-W. Tetrahedron Lett. 2008, 49, 610.
[16] Cahiez, G.; Moyeux, A.; Buendia J.; Duplais, C. J. Am. Chem. Soc. 2007, 129, 13788.
[17] Zhou, Z.-M.; Xue, W.-Z. J. Organomet. Chem. 2009, 694, 599.
[18] Krasovskiy, A.; Tishkov, A.; Amo, V. D.; Mayr, H.; Knochel, P. Angew. Chem., Int. Ed. 2006, 45, 5010.
[19] Cotton, F. A.; Faut, O. D.; Goodgame, D. M. L. J. Am. Chem. Soc. 1961, 83, 344.
[20] Lin, H.-M.; Tang, Y.; Li, Z.-H.; Liu, K.-D.; Yang, J.; Zhang, Y.-M. ARKIVOC 2012, viii, 146.
[21] Xu, X.-L.; Cheng, D.-P.; Pei, W. J. Org. Chem. 2006, 71, 6637.
[22] Kar, A.; Mangu, N.; Kaiser, H. M. J. Organomet. Chem. 2009, 694, 524.
[23] Anirban, A.; Mangua, N.; Kaiser, H. M.; Tse, M. K. Organometallic 2009, 28, 2915.
[24] Sicoli, G.; Kreidler, D.; Czesla, H.; Hopf, H.; Schurig, V. Chirality 2008, 21, 183.
[25] Morton, T. H.; Beauchamp, J. L. J. Am. Chem. Soc. 1975, 97, 2355.
[26] Zeng, M.-F.; Du, Y.-J.; Shao, L.-J.; Qi, C.-Z.; Zhang, X.-M. J. Org. Chem. 2010, 75, 2556.
[27] Rogers, D. W.; Matsunaga, N.; McLafferty, F. J.; Zavitsas, A. A.; Liebman, J. F. J. Org. Chem. 2004, 69, 7143.
[28] Freitas, S. C.; Barcellos, M. A.; Ricordi, G. V.; Pena, M. J.; Perin, G.; Jacob, G. R.; Lenard?o, J. E.; Alves, D. Green Chem. 2011, 13, 2931.
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