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2013 , Vol. 33 >Issue 02: 319 - 324

DOI: https://doi.org/10.6023/cjoc201210004

研究论文

无配体参与钯催化烯烃与芳基三烷氧基硅烷的交叉偶联反应

  • 唐伯孝 ,
  • 方小牛 ,
  • 匡仁云 ,
  • 周小春
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  • 井冈山大学化学化工学院 应用化学研究所 江西省配位化学重点实验室 吉安 343009

收稿日期: 2012-10-07

  修回日期: 2012-11-15

  网络出版日期: 2012-11-20

基金资助

江西省教育厅科技(No. GJJ12471)和井冈山大学博士启动基金(No. JZ10042)资助项目.

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Ligand-Free Pd-Catalyzed Cross-Coupling Reaction of Olefins and Trialkoxyarylsilanes

  • Tang Boxiao ,
  • Fang Xiaoniu ,
  • Kuang Renyun ,
  • Zhou Xiaochun
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  • School of Chemistry and Chemical Engineering, Institute of Applied Chemistry, and Key Laboratory of Coordination Chemistry of Jiangxi Province, Jinggangshan University, Ji'an 343009

Received date: 2012-10-07

  Revised date: 2012-11-15

  Online published: 2012-11-20

Supported by

Project supported by the Science and Technology Project of Jiangxi Provincial Department of Education (No. GJJ12471) and the Doctoral Program of Jinggangshan University (No. JZ10042).

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摘要

考察了钯催化下一系列烯烃化合物与不同芳基三烷氧基硅烷的反应, 发展了一种新型无配体参与的Heck类型反应方法. 研究表明: 以Pd(OAc)2为催化剂, 在K2CO3, n-Bu4NF·3H2O和AgOAc存在下, 该Heck类型反应能够得到中等及优良的偶联产率, 并且表现出较高的区域选择性和立体选择性. 根据实验结果以及相关文献, 对该Heck类型偶联反应的可能机理进行了探讨.

关键词： 无配体; 钯催化; Heck类型反应; 芳基三烷氧基硅烷

本文引用格式

唐伯孝 , 方小牛 , 匡仁云 , 周小春 . 无配体参与钯催化烯烃与芳基三烷氧基硅烷的交叉偶联反应[J]. 有机化学, 2013 , 33(02) : 319 -324 . DOI: 10.6023/cjoc201210004

Abstract

A ligand-free Pd-catalyzed method was developed for Heck-type reaction of a wide range of olefins with various trialkoxyarylsilanes. In the presence of Pd(OAc)2, K2CO3, TBAF?3H2O and AgOAc, the cross-coupling products can be obtained in moderate to good yields, and the Heck-type reaction displayed high regio- and stereo-selectivities. The mechanism of Heck-type reaction was discussed according to our experimental results and the reported mechanism.

Key words： ligand-free; palladium-catalyst; Heck-type reaction; trialkoxyarylsilanes

参考文献

[1] (a) de Meijere, A.; Diederich, F. Metal-Catalyzed Cross-Coupling Reactions, Wiley-VCH, Weinheim, Germany, 2004.
(b) Beller, M.; Bolm, C. Transition Metals for Organic Synthesis, 2nd ed., Wiley-VCH, Weinheim, Germany, 2004.
(c) Ritleng, V.; Sirlin, C.; Pfeffer, M. Chem. Rev. 2002, 102, 1731.
(d) Xu, Q.; Zhao, C.; Zhou, Y.; Yin, S.; Han, L. Chin. J. Org. Chem. 2012, 32, 1761 (in Chinese). (徐清, 赵长秋, 周永波, 尹双凤, 韩立彪, 有机化学, 2012, 32, 1761.)
(e) Magano, J.; Dunet, J. R. Chem. Rev. 2011, 111, 2177.
(f) Xie, Y.; Song, R.; Xiang, J.; Li, J. Chin. J. Org. Chem. 2012, 32, 1555 (in Chinese). (谢叶香, 宋仁杰, 向建南, 李金恒, 有机化学, 2012, 32, 1555.)

[2] (a) Oestreich, M. The Mizoroki-Heck Reaction, Wiley, Chichester, UK, 2009.
(b) Miyaura, N. Cross-Coupling Reaction, Springer, Berlin, 2002.
(c) Beletskaya, I. P.; Cheprakov, A. V. Chem. Rev. 2000, 100, 3009.
(d) Nicolaou, K. C.; Sorensen, E. J. Classics in Total Synthesis, VCH, New York, 1996, Chapter 31.
(e) Link, J. T.; Overman, L. E. In Metal-Catalyzed Cross-Coupling Reactions, Eds.: Diederich, F.; Stang, P. J., Wiley-VCH, New York, 1998, Chapter 6.

[3] (a) Heck, R. F.; Nolley, J. P. J. Org. Chem. 1972, 37, 2320.
(c) Ikeda, Y.; Nakamura, T.; Yorimitsu, H.; Oshima, K. J. Am. Chem. Soc. 2002, 124, 6514.
(d) Li, J.-H.; Wang, D.-P.; Xie, Y.-X. Synthesis 2005, 2193.
(e) Ren, G.; Cui, X.; Yang, E.; Yang, F.; Wu, Y. Tetrahedron 2010, 66, 4022.
(f) Wu, X.; Pei, W. Chin. J. Chem. 2009, 27, 963.
(g) Zhou, R.; Yu, X.; Wang, W.; Fu, H.; Li, R.; Chen, H.; Li, X. Chin. J. Org. Chem. 2011, 31, 1490 (in Chinese). (周蓉, 余晓军, 汪伟, 付海燕, 李瑞祥, 陈华, 李贤均, 有机化学, 2011, 31, 1490.)

[4] (a) Hirabayashi, K.; Nishihara, Y.; Mori, A.; Hiyama, T. Tetrahedron Lett. 1998, 39, 7893.
(b) Hirabayashi, K.; Ando, J.; Kawashima, J.; Nishihara, Y.; Mori, A.; Hiyama, T. Bull. Chem. Soc. Jpn. 2000, 73, 1409.

[5] Zhou, H.; Xu, Y.-H.; Chung, W.-J.; Loh, T.-P. Angew. Chem., Int. Ed. 2009, 48, 5355.

[6] (a) Mino, T.; Shibuya, M.; Suzuki, S.; Hirai, K.; Sakamoto, M.; Fujita, T. Tetrahedron 2012, 68, 429.
(b) Ye, Z.; Chen, F.; Luo, F.; Wang, W.; Lin, B.; Jia, X.; Cheng, J. Synlett 2009, 2198.

[7] (a) Amatore, C.; Jutand, A. Acc. Chem. Res. 2000, 33, 314.
(b) Nakao, Y.; Hiyama, T. Chem. Soc. Rev. 2011, 40, 4893.

[8] (a) Masllorens, J.; Moreno-Manas, M.; Pla-Quintana, A.; Roglans, A. Org. Lett. 2003, 5, 1559.
(b) Mino, T.; Shindo, H.; Kaneda, T.; Koizumi, T.; Kasashima, Y.; Sakamoto, M.; Fujita, T. Tetrahedron Lett. 2009, 50, 5358.
(c) Usui, I.; Schmidt, S.; Keller, M.; Breit, B. Org. Lett. 2008, 10, 1207.
(d) Yoo, K. S.; Yoon, C. H.; Jung, K. W. J. Am. Chem. Soc. 2006, 128, 16384.
(e) Zhu, M.-K.; Zhao, J.-F.; Loh, T.-P. Org. Lett. 2011, 13, 6308
(f) Zhou, L.; Wang, L. Synthesis 2006, 2653.
(g) Nishina, N.; Yamamoto, Y. Tetrahedron 2009, 65, 1799.
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