Synthesis of aryl thioethers through the N -chlorosuccinimide-promoted cross-coupling reaction of thiols with Grignard reagents

Journal of Organic Chemistry

Volumn 77, Issue 22, 2012, Pages 10369-10374

  Cheng, Jun Hao ^a   Ramesh, Chintakunta ^a   Kao, Hsin Lun ^a   Wang, Yu Jen ^a   Chan, Chien Ching ^a   Lee, Chin Fa ^a  

^a NATIONAL CHUNG HSING UNIVERSITY   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

ALTERNATIVE APPROACH; ARYL SULFIDES; CROSS COUPLING REACTIONS; GRIGNARD REAGENT; MILD REACTION CONDITIONS; N-CHLOROSUCCINIMIDE; ONE POT; REACTION CONDITIONS; SHORT REACTION TIME; THIOETHERS;

FUNCTIONAL GROUPS; SULFUR COMPOUNDS;

CHEMICAL REACTIONS;

CHLORIDE; CHLOROSUCCINIMIDE; ESTER; FUNCTIONAL GROUP; GRIGNARD REAGENT; SUCCINIMIDE DERIVATIVE; SULFENYLCHLORIDE; SULFIDE; THIOL; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CROSS COUPLING REACTION; ONE POT SYNTHESIS; REACTION TIME;

CATALYSIS; CROSS-LINKING REAGENTS; INDICATORS AND REAGENTS; MOLECULAR STRUCTURE; SUCCINIMIDES; SULFHYDRYL COMPOUNDS; SULFIDES;

EID: 84869162751     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo302088t     Document Type: Article

References (70)

1. Jones, D. N. In Comprehensive Organic Chemistry; Barton, D. H., Ollis, D. W., Eds.; Pergamon: New York, 1979; Vol. 3.
2. 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
3. Nielsen, S. F.; Nielsen, E. O.; Olsen, G. M.; Liljefors, T.; Peters, D. J. Med. Chem. 2000, 43, 2217
4. Gangjee, A.; Zeng, Y.; Talreja, T.; McGuire, J. J.; Kisliuk, R. L.; Queener, S. F. J. Med. Chem. 2007, 50, 3046
5. Liu, G.; Huth, J. R.; Olejniczak, E. T.; Mendoza, F.; Fesik, S. W.; von Geldern, T. W. J. Med. Chem. 2001, 44, 1202
6. 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
7. DeMartino, G.; Edler, M. C.; LaRegina, G.; 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
8. Migita, T.; Shimizu, T.; Asami, Y.; Shiobara, J.; Kato, Y.; Kosugi, M. Bull. Chem. Soc. Jpn. 1980, 53, 1385
9. Kosugi, M.; Ogata, T.; Terada, M.; Sano, H.; Migita, T. Bull. Chem. Soc. Jpn. 1985, 58, 3657
10. Itoh, T.; Mase, T. Org. Lett. 2004, 6, 4587
11. Zheng, N.; McWilliams, J. C.; Fleitz, F. J.; Armstrong, J. D., III; Volante, R. P. J. Org. Chem. 1998, 63, 9606
12. Fernández-Rodríguez, M. A.; Shen, Q.; Hartwig, J. F. J. Am. Chem. Soc. 2006, 128, 2180
13. Mispelaere-Canivet, C.; Spindler, J.-F.; Perrio, S.; Beslin, P. Tetrahedron 2005, 61, 5253
14. Fernández-Rodríguez, M. A.; Shen, Q.; Hartwig, J. F. Chem.-Eur. J. 2006, 12, 7782
15. Schopfer, U.; Schlapbach, A. Tetrahedron 2001, 57, 3069
16. Alvaro, E.; Hartwig, J. F. J. Am. Chem. Soc. 2009, 131, 7858
17. Fernández-Rodríguez, M. A.; Hartwig, J. F. J. Org. Chem. 2009, 74, 1663
18. Zhang, Y.; Ngeow, K. N.; Ying, J. Y. Org. Lett. 2007, 9, 3495
19. Percec, V.; Bae, J.-Y.; Hill, D. H. J. Org. Chem. 1995, 60, 6895
20. Chen, C.-K.; Chen, Y.-W.; Lin, C.-H.; Lin, H.-P.; Lee, C.-F. Chem. Commun. 2010, 46, 282
21. Kao, H.-L.; Chen, C.-K.; Wang, Y.-J.; Lee, C.-F. Eur. J. Org. Chem. 2011, 1776
22. Cheng, J.-H.; Yi, C.-L.; Liu, T.-J.; Lee, C.-F. Chem. Commun. 2012, 48, 8440
23. Herradura, P. S.; Pendola, K. A.; Guy, R. K. Org. Lett. 2000, 2, 2019
24. Bates, C. G.; Gujadhur, R. K.; Venkataraman, D. Org. Lett. 2002, 4, 2803
25. Palomo, C.; Oiarbide, M.; López, R.; Gómez-Bengoa, E. Tetrahedron Lett. 2000, 41, 1283
26. Kwong, F. Y.; Buchwald, S. L. Org. Lett. 2002, 4, 3517
27. Carril, M.; SanMartin, R.; Domínguez, E.; Tellitu, I. Chem.-Eur. J. 2007, 13, 5100
28. Savarin, C.; Srogl, J.; Liebeskind, L. S. Org. Lett. 2002, 4, 4309
29. Sperotto, E.; Klink, G. P. M. V.; de Vries, J. G.; Koten, G. V. J. Org. Chem. 2008, 73, 5625
30. Buchwald, S. L.; Bolm, C. Angew. Chem., Int. Ed. 2009, 48, 5586
31. Ku, X.; Huang, H.; Jiang, H.; Liu, H. J. Comb. Chem. 2009, 11, 338
32. Larsson, P.-F.; Correa, A.; Carril, M.; Norrby, P.-O.; Bolm, C. Angew. Chem., Int. Ed. 2009, 48, 5691
33. Ley, S. V.; Thomas, A. W. Angew. Chem., Int. Ed. 2003, 42, 5400
34. Bates, C. G.; Saejueng, P.; Doherty, M. Q.; Venkataraman, D. Org. Lett. 2004, 6, 5005
35. Zhu, D.; Xu, L.; Wu, F.; Wan, B. S. Tetrahedron Lett. 2006, 47, 5781
36. Verma, A. K.; Singh, J.; Chaudhary, R. Tetrahedron Lett. 2007, 48, 7199
37. Lv, X.; Bao, W. J. Org. Chem. 2007, 72, 3863
38. Lai, C.-S.; Kao, H.-L.; Wang, Y.-J.; Lee, C.-F. Tetrahedron Lett. 2012, 53, 4365
39. Arisawa, M.; Suzuki, T.; Ishikawa, T.; Yamaguchi, M. J. Am. Chem. Soc. 2008, 130, 12214
40. Wong, Y.-C.; Jayanth, T. T.; Cheng, C.-H. Org. Lett. 2006, 8, 5613
41. Lin, Y.-Y.; Wang, Y.-J.; Lin, C.-H.; Cheng, J.-H.; Lee, C.-F. J. Org. Chem. 2012, 77, 6100
42. Wu, J.-R.; Lin, C.-H.; Lee, C.-F. Chem. Commun. 2009, 4450
43. Correa, A.; Carril, M.; Bolm, C. Angew. Chem., Int. Ed. 2008, 47, 2880
44. Reddy, V. P.; Swapna, K.; Kumar, A. V.; Rao, K. R. J. Org. Chem. 2009, 74, 3189
45. Vu, V. A.; Bérillon, L.; Knochel, P. Tetrahedron Lett. 2001, 42, 6847
46. Stoll, A. H.; Krasovskiy, A.; Knochel, P. Angew. Chem., Int. Ed. 2006, 45, 606
47. Baker, R. W.; Pocock, G. R.; Sargent, M. V. J. Chem. Soc., Chem. Commun. 1993, 1489
48. Francisco, M. A.; Kurs, A. J. Org. Chem. 1988, 53, 4821
49. Ham, J.; Yang, I.; Kang, H. J. Org. Chem. 2004, 69, 3236
50. Deng, K.; Bensari-Bouguerra, A.; Whetstone, J.; Cohen, T. J. Org. Chem. 2006, 71, 2360
51. Truce, W. E.; Ray, W. J., Jr. J. Am. Chem. Soc. 1959, 81, 481
52. Zhou, L.; Tan, C. K.; Jiang, X.; Chen, F.; Yeung, Y.-Y. J. Am. Chem. Soc. 2010, 132, 15474
53. Wei, Y.; Lin, S.; Liang, F. Org. Lett. 2012, 14, 4202
54. Zhou, L.; Tan, C. K.; Zhou, J.; Yeung, Y.-Y. J. Am. Chem. Soc. 2010, 132, 10245
55. Kalyani, D.; Dick, A. R.; Anani, W. Q.; Melanie, S.; Sanford, M. S. Org. Lett. 2006, 8, 2523
56. Kim, D. W.; Choi, H. Y.; Lee, K. J.; Chi, D. Y. Org. Lett. 2001, 3, 445
57. Liu, X.; Zhang, Y.; Wang, L.; Fu, H.; Jiang, Y.; Zhao, Y. J. Org. Chem. 2008, 73, 6207
58. Barker, T. J.; Jarvo, E. R. Angew. Chem., Int. Ed. 2011, 50, 8325
59. Jithunsa, M.; Ueda, M.; Miyata, O. Org. Lett. 2011, 13, 518
60. Sharma, V. B.; Jain, S. L.; Sain, B. J. Mol. Catal. A: Chem. 2005, 227, 47
61. Sai, M.; Matsubara, S. Org. Lett. 2011, 13, 4676
62. Tunge, J. A.; Mellegaard, S. R. Org. Lett. 2004, 6, 1205
63. Schlosser, K. M.; Krasutsky, A. P.; Hamilton, H. W.; Reed, J. S.; Sexton, K. Org. Lett. 2004, 6, 819
64. Kroll, F.; Morphy, R.; Rees, D.; Gani, D. Tetrahedron Lett. 1997, 38, 8573
65. Yadav, J. S.; Reddy, B. V. S.; Jain, R.; Baishya, G. Tetrahedron Lett. 2008, 49, 3015
66. Kamimura, A.; Sasatani, H.; Hashimoto, T.; Ono, N. J. Org. Chem. 1989, 54, 4998
67. Pastor, S. D.; Hessell, E. T. J. Org. Chem. 1985, 50, 4812
68. Rout, L.; Saha, P.; Jammi, S.; Punniyamurthy, T. Eur. J. Org. Chem. 2008, 640
69. Ajiki, K.; Hirano, M.; Tanaka, K. Org. Lett. 2005, 7, 4193
70. Norris, T.; Leeman, K. Org. Process Res. Dev. 2008, 12, 869