CuI-catalyzed coupling reactions of aryl iodides and bromides with thiols promoted by amino acid ligands

Synlett

Volumn , Issue 7, 2004, Pages 1254-1258

  Deng, Wei ^a   Zou, Yan ^a   Wang, Ye Feng ^a   Liu, Lei ^a   Guo, Qing Xiang ^a  

^a UNIVERSITY OF SCIENCE AND TECHNOLOGY OF CHINA   (China)

Author keywords

Amino acid ligand; Aryl sulfide; Copper iodide; Cross coupling

Indexed keywords

AMINO ACID DERIVATIVE; BROMINE DERIVATIVE; IODINE DERIVATIVE; LIGAND; THIOL DERIVATIVE;

ADDITION REACTION; AMIDATION; ARTICLE; CATALYSIS; CHEMICAL REACTION; OXIDATION;

EID: 2942746695     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-825584     Document Type: Article

References (30)

1. (a) Arguello, J. E.; Schmidt, L. C.; Penenory, A. B. Org. Lett. 2003, 5, 4133.
2. (b) Zhang, X.-M.; Ma, M.; Wang, J.-B. Chin. J. Chem. 2003, 21, 878.
3. (c) Yao, H.; Richardson, D. E. J. Am. Chem. Soc. 2003, 125, 6211.
4. (d) Savarin, C.; Srogl, J.; Liebeskind, L. S. Org. Lett. 2002, 4, 4309.
5. (e) Nose, M.; Suzuki, H. Synthesis 2002, 1065.
6. Kondo, T.; Mitsudo, T. Chem. Rev. 2000, 100, 3205.
7. (a) Moreau, X.; Campagne, J.-M. J. Organomet. Chem. 2003, 687, 322.
8. (b) Wolf, C.; Lerebours, R. J. Org. Chem. 2003, 68, 7077.
9. (c) Baskin, J. M.; Wang, Z. Org. Lett. 2002, 4, 4423.
10. (d) Li, G. Y. J. Org. Chem. 2002, 67, 3643.
11. (e) Schopfer, U.; Schlapbach, A. Tetrahedron 2001, 57, 3069.
12. Very recent reviews: (a) Kunz, K.; Scholz, U.; Ganzer, D. Synlett 2003, 2438. (b) Ley, S. V.; Thomas, A. W. Angew. Chem. Int. Ed. 2003, 42, 5400. (c) Deng, W.; Liu, L.; Guo, Q.-X. Chin. J. Org. Chem. 2004, 24, 150.
13. Very recent reviews: (a) Kunz, K.; Scholz, U.; Ganzer, D. Synlett 2003, 2438. (b) Ley, S. V.; Thomas, A. W. Angew. Chem. Int. Ed. 2003, 42, 5400. (c) Deng, W.; Liu, L.; Guo, Q.-X. Chin. J. Org. Chem. 2004, 24, 150.
14. Very recent reviews: (a) Kunz, K.; Scholz, U.; Ganzer, D. Synlett 2003, 2438. (b) Ley, S. V.; Thomas, A. W. Angew. Chem. Int. Ed. 2003, 42, 5400. (c) Deng, W.; Liu, L.; Guo, Q.-X. Chin. J. Org. Chem. 2004, 24, 150.
15. Lindley, J. Tetrahedron 1984, 40, 1433.
16. Bates, C. G.; Gujadhur, R. K.; Venkataraman, D. Org. Lett. 2002, 4, 2803.
17. Kwong, F. Y.; Buchwald, S. L. Org. Lett. 2002, 4, 3517.
18. Wu, Y.-J.; He, H. Synlett 2003, 1789.
19. Naus, P.; Leseticky, L.; Smrcek, S.; Tislerova, I.; Sticha, M. Synlett 2003, 2117.
20. (a) Ma, D.; Zhang, Y.; Yao, J.; Wu, S.; Tao, F. J. Am. Chem. Soc. 1998, 120, 12459.
21. (b) Ma, D.; Xia, C. Org. Lett. 2001, 3, 2583.
22. (a) Ma, D.; Cai, Q.; Zhang, H. Org. Lett. 2003, 5, 2453.
23. (b) Ma, D.; Cai, Q. Org. Lett. 2003, 5, 3799.
24. (c) Ma, D.; Cai, Q. Synlett 2004, 128.
25. (d) Zhu, W.; Ma, D. Chem. Commun. 2004, 888.
26. Deng, W.; Wang, Y.-F.; Zou, Y.; Liu, L.; Guo, Q.-X. Tetrahedron Lett. 2004, 45, 2311.
27. (a) Cohen, T.; Cristea, I. J. Am. Chem. Soc. 1976, 98, 748.
28. (b) See ref. 1d.
29. All the products are known compounds except for 1,4-bis(octylthio) benzene.
30. 2: C, 72.06; H, 10.46. Found: C, 72.20; H, 10.58.