Base-free Cu (II)-catalyzed coupling reaction of arylboronic acids and thiols

Chinese Journal of Organic Chemistry

Volumn 33, Issue 2, 2013, Pages 343-347

  Yang, Minghua ^a   Pei, Ji ^a   Yan, Guobing ^a   Weng, Qiuyue ^a  

^a Lishui Architecture Design and Research Institute   (China)

Author keywords

1, 10 phenanthroline; Arylboronic acid; Coupling reaction; Cupric acetate; Thiol

Indexed keywords

EID: 84876314353     PISSN: 02532786     EISSN: None     Source Type: Journal    
DOI: 10.6023/cjoc201209008     Document Type: Article

References (33)

1. Neilsen, S. F.; Neilsen, E. O.; Olsen, G. M.; Liljefors, T.; Peters, D. J. Med. Chem. 2000, 43, 2217.
2. Navarro, R.; Perrino, M. P.; Tardajos, M. G.; Reinecke, H. Macromolecules 2010, 43, 2377.
3. Guilarte, V.; Fernández-Rodríguez, M. A.; García-García, P.; Hernando, E.; Sanz, R. Org. Lett. 2011, 13, 5100.
4. Taniguchi, N. J. Org. Chem. 2004, 69, 6904.
5. Kwong, F. Y.; Buchwald, S. L. Org. Lett. 2002, 4, 3517.
6. Lv, X.; Bao, W.-L. J. Org. Chem. 2007, 72, 3863.
7. Sperotto, E.; Klink, G. P. M.; Vries, J. G.; Koten, G. J. Org. Chem. 2008, 73, 5625.
8. Yudin, A. K. Catalyzed Carbon-Heteroatom Bond Formation, Wiley-VCH, Weinheim, 2010, pp. 69-113.
9. Bichler, P.; Love, J. A. Top. Organomet. Chem. 2010, 31, 39.
10. Eichman, C. C.; Stambuli, J. P. Molecules 2011, 16, 590.
11. Jiang, Y.; Qin, Y.; Xie, S.; Zhang, X.; Dong, J.; Ma, D. Org. Lett. 2009, 11, 5250.
12. Ke, F.; Qu, Y.; Jiang, Z.; Li, Z.; Wu, D.; Zhou, X. Org. Lett. 2011, 13, 545.
13. 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.
14. Firouzabadi, H.; Iranpoor, N.; Gholinejad, M. Adv. Synth. Catal. 2010, 119.
15. Jiang, Z.; She, J.; Lin, X.-F. Adv. Synth. Catal. 2009, 2558.
16. Kumar, S.; Engman, L. J. Org. Chem. 2006, 71, 5400.
17. Herradura, P. S.; Pendola, K. A.; Guy, R. K. Org. Lett. 2000, 2, 2019.
18. Jammi, S.; Sakthivel, S.; Rout, L.; Mukherje, T.; Mandal, S.; Mitra, R.; Sha, P.; Punniyamurthy, T. J. Org. Chem. 2009, 74, 1971.
19. Savarin, C.; Srogl, J.; Liebeskind, L. S. Org. Lett. 2002, 4, 4309.
20. Taniguchi, N. J. Org. Chem. 2007, 72, 1241.
21. Taniguchi, N. Synlett 2006, 1351.
22. Luo, P.-S.; Wang, F.; Li, J.-H.; Tang, R.-Y.; Zhong, P. Synthesis 2009, 921.
23. Xu, H.; Zhao, Y.; Feng, T.; Feng, Y. J. Org. Chem. 2012, 77, 2878.
24. Yang, M.; Zhu, C.; Yuan, F.; Huang, Y.; Pan, Y. Org. Lett. 2005, 7, 1927.
25. Yang, M.; Liu, F. J. Org. Chem. 2007, 72, 8969.
26. Yang, M.; Yan, G.; Zheng, Y. Tetrahedron Lett. 2008, 49, 6471.
27. Yang, M.; Pei, J.; Yan, G.; Zheng, Y. Lett. Org. Chem. 2011, 8, 587.
28. Hall, D. G.; Suzuki, A. In Boronic Acids, Vol. 2, Ed.: Hall, D. G., Wiley-VCH Verlag, Weinheim, 2011, p. 9.
29. Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457.
30. Hayashi, T.; Yamasaki, K. Chem. Rev. 2003, 103, 2829.
31. 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].
32. Liu, L.-F.; Zhang, Y.-H.; Wang, Y. G. J. Org. Chem. 2005, 70, 6122.
33. Xin, B.-W. Ph. D. Dissertation, Zhejiang University, Hangzhou, 2010, p. 18 (in Chinese).