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

doi:10.6023/cjoc201209008

Chin. J. Org. Chem. ›› 2013, Vol. 33 ›› Issue (02): 343-347.DOI: 10.6023/cjoc201209008 Previous Articles Next Articles

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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

丽水学院理学院丽水 323000

收稿日期:2012-09-06 修回日期:2012-10-17 发布日期:2012-10-25
通讯作者: 杨明华 E-mail:mhyang@lsu.edu.cn
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

Colllege of Science, Lishui Universtiy, Lishui 323000

Received:2012-09-06 Revised:2012-10-17 Published:2012-10-25
Supported by:
Project supported by the Natural Science Foundation of Zhejiang Province (No. Y407081).

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℃.

Key words: coupling reaction, thiol, arylboronic acid, 1,10-phenanthroline, cupric acetate

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Yang Minghua, Pei Ji, Yan Guobing, Weng Qiuyue. Base-Free Cu(II)-Catalyzed Coupling Reaction of Arylboronic Acids and Thiols[J]. Chin. J. Org. Chem., 2013, 33(02): 343-347.

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[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.)

无碱参与的铜催化芳基硼酸和硫酚的偶联反应研究

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

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