Indium-catalyzed C-S cross-coupling of aryl halides with thiols

Journal of Organic Chemistry

Volumn 74, Issue 8, 2009, Pages 3189-3191

  Reddy, V Prakash ^a   Swapna, K ^a   Kumar, A Vijay ^a   Rao, K Rama ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

ALKANE-THIOLS; ARYL HALIDES; ARYL SULFIDES; CROSS COUPLINGS; CROSS-COUPLED;

DIMETHYL SULFOXIDE; PARAFFINS;

INDIUM;

DIAMINE DERIVATIVE; DIMETHYL SULFOXIDE; HALIDE; INDIUM; IODOBENZENE; N,N,N'N' TETRAMETHYLETHYLENEDIAMINE; THIOL DERIVATIVE; THIOPHENOL; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; COUPLING FACTOR; CROSS COUPLING REACTION;

ALKANES; CARBON COMPOUNDS, INORGANIC; CATALYSIS; CROSS-LINKING REAGENTS; HYDROCARBONS, HALOGENATED; INDIUM; IODOBENZENES; MESYLATES; MOLECULAR STRUCTURE; SULFHYDRYL COMPOUNDS; SULFIDES;

EID: 65249101511     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo802731j     Document Type: Article

References (34)

1. (a) Liu, L.; Stelmach, J. E.; Natarajan, S. R.; Chen, M.-H.; Singh, S. B.; Schwartz, C. D.; Fitzgerald, C. E.; O'Keefe, S. J.; Zaller, D. M.; Schmatz, D. M.; Doherty, J. B. Bioorg. Med. Chem. Lett. 2003, 13, 3979.
2. (b) Kaldor, S. W.; Kalish, V. J.; Davies, J. F., II.; Shetty, B. V.; Fritz, J. E.; Appelt, K.; Burgess, J. A.; Campanale, K. M.; Chirgadze, N. Y.; Clawson, D. K.; Dressman, B. A.; Hatch, S. D.; Khalil, D. A.; Kosa, M. B.; Lubbehusen, P. P.; Muesing, M. A.; Patick, A. K.; Reich, S. H.; Su, K. S.; Tatlock, J. H. J. Med. Chem. 1997, 40, 3979.
3. Liu, G.; Huth, J. R.; Olejniczak, E. T.; Mendoza, R.; DeVries, P.; Leitza, S.; Reilly, E. B.; Okasinski, G. F.; Fesik, S. W.; von Geldern, T. W. J. Med. Chem. 2001, 44, 1202.
4. (a) Mispelaere-Canivet, C.; Spindler, J.-F.; Perrio, S.; Beslin, P. Tetrahedron 2005, 61, 5253.
5. (b) Itoh, T.; Mase, T. Org. Lett. 2004, 6, 4587.
6. (c) Fernández Rodríguez, M. A.; Shen, Q.; Hartwig, J. F. J. Am. Chem. Soc. 2006, 128, 2180.
7. (d) Murata, M.; Buchwald, S. L. Tetrahedron 2004, 60, 7397.
8. (e) Schopfer, U.; Schlapbach, A. Tetrahedron 2001, 57, 3069.
9. (f) Li, G. Y. Angew. Chem. 2001, 113, 1561; Angew. Chem., Int. Ed. 2001, 40, 1513.
10. (g) BarbiKri, R. S.; Bellato, C R.; Dias, A. K. C.; Massabni, A. C. Catal. Lett. 2006, 109, 171.
11. (h) Dickens, M. J.; Gilday, J. P.; Mowlem, T. J.; Widdowson, D. A. Tetrahedron 1991, 47, 8621.
12. (i) Ishiyama, T.; Mori, M.; Suzuki, A.; Miyaura, N. J. Organomet. Chem. 1996, 525, 225.
13. (j) Zheng, N.; McWilliams, J. C.; Fleitz, F. J.; Armstrong, J. D.; Volante, R. P. J. Org. Chem. 1998, 63, 9606.
14. (k) Mann, G; Baranano, D.; Hartwig, J. F.; Rheingold, A. L.; Guzei, I. A. J. Am. Chem. Soc. 1998, 120, 9205.
15. (a) Cristau, H. J.; Chabaud, B.; Chene, A.; Christol, H. Synthesis 1981, 892.
16. (b) Millois, C.; Diaz, P. Org. Lett. 2000, 2, 1705.
17. (c) Percec, V.; Bae, J.-Y.; Hill, D. H. J. Org. Chem. 1995, 60, 6895.
18. (d) Takagi, K. Chem. Lett. 1987, 2221.
19. (a) Bates, C. G.; Gujadhur, R. K.; Venkataraman, D. Org. Lett. 2002, 4, 2803.
20. (b) Kwong, F. Y.; Buchwald, S. L. Org. Lett. 2002, 4, 3517.
21. (c) Wu, Y.-J.; He, H. Synlett 2003 1789.
22. (d) Bates, C. G.; Saejueng, P.; Doherty, M. Q.; Venkataraman, D. Org. Lett. 2004, 6, 5005.
23. (e) Deng, W.; Zou, Y.; Wang, Y.- F.; Liu, L.; Guo, Q.-X. Synlett 2004, 1254.
24. (f) Palomo, C.; Oiarbide, M.; Lopez, R.; Gomez-Bengoa, E. Tetrahedron Lett. 2000, 41, 1283.
25. (g) Savarin, C.; Srogl, J.; Liebeskind, L. S. Org. Lett. 2002, 4, 4309.
26. (h) Herradura, P. S.; Pendola, K. A.; Guy, R. K. Org. Lett. 2000, 2, 2019.
27. (i) Chen, Y.-J.; Chen, H.-H. Org. Lett. 2006, 8, 5609.
28. (j) Zhu, D.; Xu, L.; Wu, F.; Wan, B. S. Tetrahedron Lett. 2006, 47, 5781.
29. (k) Ley, S. V.; Thomas, A. W. Angew. Chem. 2003, 115, 5558; Angew. Chem., Int. Ed. 2003, 42, 5400.
30. (l) Sperotto, E.; Klink, G. P. M. V.; De Vries, J. G.; Koten, G. V. J. Org. Chem. 2008, 73, 5625.
31. (m) She, J.; Jiang, Z.; Wang, Y. Tetrahedron Lett. 2009, 50, 593.
32. Wong, Y.-C.; Jayanth, T. T.; Cheng, C.-H. Org. Lett. 2006, 8, 5613.
33. Correa, A.; Carril, M.; Bolm, C. Angew. Chem., Int. Ed. 2008, 47, 2880.
34. See the Supporting Information.