Cu-catalyzed one-pot synthesis of unsymmetrical diaryl thioethers by coupling of aryl halides using a thiol precursor

Organic Letters

Volumn 13, Issue 5, 2011, Pages 1008-1011

  Prasad, D J C ^a   Sekar, Govindasamy ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY MADRAS   (India)

Author keywords

[No Author keywords available]

Indexed keywords

BENZOTHIAZOLE DERIVATIVE; COPPER; ETHYLXANTHATE; SULFIDE; THIOKETONE; THIOL DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; COMBINATORIAL CHEMISTRY; SYNTHESIS;

BENZOTHIAZOLES; CATALYSIS; COMBINATORIAL CHEMISTRY TECHNIQUES; COPPER; MOLECULAR STRUCTURE; SULFHYDRYL COMPOUNDS; SULFIDES; THIONES;

EID: 79952127755     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol103041s     Document Type: Article

References (51)

1. Jones, D. N. In Comprehensive Organic Chemistry; Barton, D. H.; Ollis, D. W., Eds.; Pergamon: New York, 1979; Vol. 3.
2. Rayner, C. M. Contemp. Org. Synth. 1996, 3, 499
3. Kondo, T.; Mitsudo, T. Chem. Rev. 2000, 100, 3205
4. Ley, S. V.; Thomas, A. W. Angew. Chem., Int. Ed. 2003, 42, 5400
5. Marcincal-Lefebvre, A.; Gesquiere, J. C.; Lemer, C. J. Med. Chem. 1981, 24, 889
6. Liu, G.; Link, J. T.; Pei, Z.; Reilly, E. B.; Leitza, S.; Nguyen, B.; Marsh, K. C.; Okasinski, G. F.; Von Geldern, T. W.; Ormes, M.; Fowler, K.; Gallatin, M. J. Med. Chem. 2000, 43, 4025
7. Aiello, S.; Wells, G.; Stone, E. L.; Kadri, H.; Bazzi, R.; Bell, D. R.; Stevens, M. F. G.; Matthews, C. S.; Bradshaw, T. D.; Westwell, A. D. J. Med. Chem. 2008, 51, 5135
8. Dumas, J.; Brittelli, D.; Chen, J.; Dixon, B.; Hatoum-Mokdad, H.; Konig, G.; Sibley, R.; Witowsky, J.; Wong, S. Bioorg. Med. Chem. Lett. 1999, 9, 2531
9. Moracci, F. M.; Liberatore, F.; Micheletti, F.; Liso, G.; Cardellini, M. J. Med. Chem. 1974, 17, 463
10. 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.; Lubbenhusen, P. P.; Muesing, M. A.; Patick, A. K.; Reich, S. H.; Su, K. S.; Tatlock, J. H. J. Med. Chem. 1997, 40, 3979
11. 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
12. Martino, G. D.; Edler, M. C.; Regina, G. L.; Coluccia, A.; Barbera, M. C.; Barrow, D.; Nicholson, R. I.; Chiosis, G.; Brancale, A.; Hamel, E.; Artico, M.; Silvestri, R. J. Med. Chem. 2006, 49, 947
13. Bierbeek, A. V.; Gingras, M. Tetrahedron Lett. 1998, 39, 6283
14. Campbell, J. R. J. Org. Chem. 1964, 29, 1830
15. Ham, J.; Yang, I.; Kang, H. J. Org. Chem. 2004, 69, 3236
16. Lindley, J. Tetrahedron 1984, 40, 1433
17. For selected Pd-catalyzed S-arylation of thiols, see: Migita, T.; Shimizu, T.; Asami, Y.; Shiobara, J.; Kato, Y.; Kosugi, M. Bull. Chem. Soc. Jpn. 1980, 53, 1385
18. Murata, M.; Buchwald, S. L. Tetrahedron 2004, 60, 7397
19. Itoh, T.; Mase, T. Org. Lett. 2004, 6, 4587
20. Fernandez-Rodroeguez, M. A.; Shen, Q.; Hartwig, J. F. J. Am. Chem. Soc. 2006, 128, 2180
21. Li, G. Y.; Zheng, G.; Noonan, A. F. J. Org. Chem. 2001, 66, 8677
22. Fernandez-Rodroeguez, M. A.; Shen, Q.; Hartwig, J. F. Chem.-Eur. J. 2006, 12, 7782
23. Schopfer, U.; Schlapbach, A. Tetrahedron 2001, 57, 3069
24. For selected copper-catalyzed S-arylation of thiols, see: Kwong, F. Y.; Buchwald, S. L. Org. Lett. 2002, 4, 3517
25. Bates, C. G.; Gujadhur, R. K.; Venkataraman, D. Org. Lett. 2002, 4, 2803
26. Chen, Y.-J.; Chen, H. H. Org. Lett. 2006, 8, 5609
27. Rout, L.; Sen, T, K.; Punniyamurthy, T. Angew. Chem., Int. Ed. 2007, 46, 5583
28. Lv, X.; Bao, W. J. Org. Chem. 2007, 72, 3863
29. Carril, M.; SanMartin, R.; Domínguez, E.; Tellitu, I. Chem.-Eur. J. 2007, 13, 5100
30. Verma, A. K.; Singh, J.; Chaudhary, R. Tetrahedron Lett. 2007, 48, 7199
31. Sperotto, E.; Klink, G. P. M. V.; de Vries, J. G.; Koten, G. V. J. Org. Chem. 2008, 73, 5625
32. Correa, A.; Carril, M.; Bolm, C. Angew. Chem., Int. Ed. 2008, 47, 2880
33. Wu, J. R.; Lin, C. H.; Lee, C. F. Chem. Commun. 2009, 4450
34. Wong, Y. C.; Jayanth, T. T.; Cheng, C. H. Org. Lett. 2006, 8, 5613
35. Reddy, V. P.; Kumar, A. V.; Swapna, K.; Rao, K. R. Org. Lett. 2009, 11, 1697
36. Sawada, N.; Itoh, T.; Yasuda, N. Tetrahedron Lett. 2006, 47, 6595
37. Lloyd-Jones, G. C.; Moseley, J. D.; Renny, J. S. Synthesis 2008, 661
38. Jiang, Y.; Qin, Y.; Xie, S.; Zhang, X.; Dong, J.; Ma, D. Org. Lett. 2009, 11, 5250
39. Fernandez-Rodroeguez, M. A.; Hartwig, J. F. Chem.-Eur. J. 2010, 16, 2355
40. Firouzabadi, H.; Iranpoor, N.; Gholinejad, M. Adv. Synth. Catal. 2010, 352, 119
41. Naidu, A. B.; Jaseer, E. A.; Sekar, G. J. Org. Chem. 2009, 74, 3675
42. Rao, R. K.; Naidu, A. B.; Sekar, G. Org. Lett. 2009, 11, 1923
43. Prasad, D. J. C.; Sekar, G. Org. Biomol. Chem. 2009, 7, 5091
44. Prasad, D. J. C.; Naidu, A. B.; Sekar, G. Tetrahedron Lett. 2009, 50, 1411
45. Prasad, D. J. C.; Sekar, G. Synthesis 2010, 79
46. Thakur, K. G.; Jaseer, E. A.; Naidu, A. B.; Sekar, G. Tetrahedron Lett. 2009, 50, 2865
47. Jaseer, E. A.; Prasad, D. J. C.; Dandapat, A.; Sekar, G. Tetrahedron Lett. 2010, 51, 5009
48. To the best of our knowledge, this is the first report for the use of potassium ethyl xanthogenate as a thiol surrogate in metal-catalyzed arylations, which is a cheaper and comercially available reagent.
49. O -Ethyl S-4-methoxyphenyl carbonodithioate 3 was isolated with good yield.
50. Itoh, T.; Mase, T. Org. Lett. 2007, 9, 3687
51. Ma, D.; Xie, S.; Xue, P.; Zhang, X.; Dong, J.; Jiang, Y. Angew. Chem., Int. Ed. 2009, 48, 4222