研究论文

无碱参与的铜催化芳基硼酸和硫酚的偶联反应研究

  • 杨明华 ,
  • 裴吉 ,
  • 严国兵 ,
  • 翁秋月
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  • 丽水学院理学院 丽水 323000

收稿日期: 2012-09-06

  修回日期: 2012-10-17

  网络出版日期: 2012-10-25

基金资助

浙江省自然科学基金(No. Y407081)资助项目.

Base-Free Cu(II)-Catalyzed Coupling Reaction of Arylboronic Acids and Thiols

  • Yang Minghua ,
  • Pei Ji ,
  • Yan Guobing ,
  • Weng Qiuyue
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  • Colllege of Science, Lishui Universtiy, Lishui 323000

Received date: 2012-09-06

  Revised date: 2012-10-17

  Online published: 2012-10-25

Supported by

Project supported by the Natural Science Foundation of Zhejiang Province (No. Y407081).

摘要

无碱参与的条件下, 研究了Cu盐催化芳基硼酸与硫酚的偶联反应. 通过反应溶剂、温度、铜盐、配体等条件的优化, 结果表明在空气中, 以1,10-菲啰啉-醋酸铜为催化剂, DMSO/H2O (V: V=1:1)作为溶剂, 反应温度为60℃, 以较高产率合成二芳基硫醚.

本文引用格式

杨明华 , 裴吉 , 严国兵 , 翁秋月 . 无碱参与的铜催化芳基硼酸和硫酚的偶联反应研究[J]. 有机化学, 2013 , 33(02) : 343 -347 . DOI: 10.6023/cjoc201209008

Abstract

Baes-free Cu(II)-catalyzed coupling reaction of arylboronic acid and thiols was described. After optimization of reaction conditions, such as solvents, reaction temperatures, copper salts and ligands, the results show that some biarylsulfides were synthesized in good yields using 1,10-phenanthroline-Cu(OAc)2·H2O as catalyst, DMSO/H2O (V: V=1:1) as solvent, under air atmosphere at 60℃.

参考文献

[1] (a) Neilsen, S. F.; Neilsen, E. O.; Olsen, G. M.; Liljefors, T.; Peters, D. J. Med. Chem. 2000, 43, 2217.

(b) Navarro, R.; Perrino, M. P.; Tardajos, M. G.; Reinecke, H. Macromolecules 2010, 43, 2377.

[2] Guilarte, V.; Ferna?ndez-Rodríguez, M. A.; García-García, P.; Hernando, E.; Sanz, R. Org. Lett. 2011, 13, 5100.

[3] Taniguchi, N. J. Org. Chem. 2004, 69, 6904.

[4] (a) Kwong, F. Y.; Buchwald, S. L. Org. Lett. 2002, 4, 3517.

(b) Lv, X.; Bao, W.-L. J. Org. Chem.2007, 72, 3863.

(c) Sperotto, E.; Klink, G. P. M.; Vries, J. G.; Koten, G. J. Org. Chem. 2008, 73, 5625.

[5] (a) Yudin, A. K. Catalyzed Carbon-Heteroatom Bond Formation, Wiley-VCH, Weinheim, 2010, pp. 69~113.

(b) Bichler, P.; Love, J. A. Top. Organomet. Chem. 2010, 31, 39.

(c) Eichman, C. C.; Stambuli, J. P. Molecules 2011, 16, 590.

[6] Jiang, Y.; Qin, Y.; Xie, S.; Zhang, X.; Dong, J.; Ma, D. Org. Lett. 2009, 11,5250.

[7] Ke, F.; Qu, Y.; Jiang, Z.; Li, Z.; Wu, D.; Zhou, X. Org. Lett. 2011, 13, 545.

[8] (a) Reddy, K. H. V.; Reddy, V. P.; Shankar, J.; Madhav, B.; Kumar, B. S. P. A.; Nageswar, Y. V. D. Tetrahedron Lett. 2011, 52, 2679.

(b) Firouzabadi, H.; Iranpoor, N.; Gholinejad, M. Adv. Synth. Catal. 2010, 119.

[9] Jiang, Z.; She, J.; Lin, X.-F. Adv. Synth. Catal. 2009, 2558.

[10] Kumar, S.; Engman, L. J. Org. Chem. 2006, 71, 5400.

[11] Herradura, P. S.; Pendola, K. A.; Guy, R. K. Org. Lett. 2000, 2, 2019.

[12] Jammi, S.; Sakthivel, S.; Rout, L.; Mukherje, T.; Mandal, S.; Mitra, R.; Sha, P.; Punniyamurthy, T. J. Org. Chem. 2009, 74, 1971.

[13] Savarin, C.; Srogl, J.; Liebeskind, L. S. Org. Lett. 2002, 4, 4309.

[14] (a) Taniguchi, N. J. Org. Chem. 2007, 72, 1241.

(b) Taniguchi, N. Synlett 2006, 1351.

(c) Luo, P.-S.; Wang, F.; Li, J.-H.; Tang, R.-Y.; Zhong, P. Synthesis 2009, 921.

[15] Xu, H.; Zhao, Y.; Feng, T.; Feng,Y. J. Org. Chem. 2012, 77, 2878.

[16] (a) Yang, M.; Zhu, C.; Yuan, F.; Huang, Y.; Pan, Y. Org. Lett. 2005, 7, 1927.

(b) Yang, M.; Liu, F. J. Org. Chem. 2007, 72, 8969.

(c) Yang, M.; Yan, G.; Zheng, Y. Tetrahedron Lett. 2008, 49, 6471.

(d) Yang, M.; Pei, J.; Yan, G.; Zheng, Y. Lett. Org. Chem. 2011, 8, 587.

[17] Hall, D. G.; Suzuki, A. In Boronic Acids, Vol. 2, Ed.: Hall, D. G., Wiley-VCH Verlag, Weinheim, 2011, p. 9.

[18] In metal-catalyzed organic reaction using organoboronic acid, water has been added: (a) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457.

(b) Hayashi, T.; Yamasaki, K. Chem. Rev. 2003, 103, 2829. Water can improve metal-catalyzed organic reaction using organoboron compounds, see:

(c) Guan, B.-T; Wang, Y.; Li, B.-J.; Yu, D.-G.; Shi, Z. -J. J. Am. Chem. Soc. 2008, 130, 14468. And also please see Ref.[14a].

[19] (a) Liu, L.-F.; Zhang, Y.-H.; Wang, Y. G. J. Org. Chem. 2005, 70, 6122.

(b) Xin, B.-W. Ph.D. Dissertation, Zhejiang University, Hangzhou, 2010, p. 18 (in Chinese). (辛炳炜, 博士论文, 浙江大学, 杭州, 2010, p. 18.)

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