Synthesis of 3-((trifluoromethyl)thio)indoles via a reaction of 2-alkynylaniline with trifluoromethanesulfanylamide

Chemical Communications

Volumn 50, Issue 5, 2014, Pages 578-580

  Sheng, Jie ^a   Li, Shaoyu ^a   Wu, Jie ^a,b  

^a FUDAN UNIVERSITY   (China)

^b SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDES; ANILINE COMPOUNDS; BISMUTH; CATALYSIS; CHLORIDES; INDOLES; PALLADIUM;

3 [(TRIFLUOROMETHYL)THIO]INDOLE DERIVATIVE; AMIDE; ANILINE; BISMUTH; BISMUTH CHLORIDE; INDOLE DERIVATIVE; PALLADIUM; TRIFLUOROMETHANESULFANYLAMIDE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CYCLIZATION; DRUG STRUCTURE; DRUG SYNTHESIS; FLUORINATION; REACTION ANALYSIS;

EID: 84890342765     PISSN: 13597345     EISSN: 1364548X     Source Type: Journal    
DOI: 10.1039/c3cc45958f     Document Type: Article

References (50)

1. R. Filler and Y. Kobayashi, Biomedicinal Aspects of Fluorine Chemistry, Elsevier, Amsterdam, 1982
2. Fluorine in Bioorganic Chemistry, ed. J. T. Welch and S. Eswarakrishman, Wiley, New York, 1991
3. Fluorinated Heterocyclic Compounds: Synthesis, Chemistry, and Applications, ed. V. A. Petrov, John Wiley & Sons, Inc. Hoboken, NJ, 2009
4. E. V. Nosova, G. N. Lipunova, V. N. Charushin, O. N. Chupakhin, J. Fluorine Chem. 2010, 131, 1267
5. S. Zhu, Y. Wang, W. Peng, L. Song, G. Jin, Curr. Org. Chem. 2002, 6, 1057
6. M. J. Silvester, Aldrichimica Acta 1991, 24, 31.
7. P. Kwiatkowski, T. D. Beeson, J. C. Conrad, D. W. C. MacMillan, J. Am. Chem. Soc. 2011, 133, 1738
8. Y. Kishi, H. Nagura, S. Inagi, T. Fuchigami, Chem. Commun. 2008, 3876
9. S. Fustero, S. Catalan, M. Sanchez-Rosello, A. Simon-Fuentes, C. del Pozo, Org. Lett. 2010, 12, 3484
10. T. Xu, G. Liu, Org. Lett. 2012, 14, 5416
11. Bioorganic and Medicinal Chemistry of Fluorine, ed. J.-P. Begue and D. Bonnet-Delpon, Wiley, Hoboken, 2008
12. C. Chen, L. Chu, F.-L. Qing, J. Am. Chem. Soc. 2012, 134, 12454
13. F. Baert, J. Colomb, T. Billard, Angew. Chem. Int. Ed. 2012, 51, 10382
14. G. Teverovskiy, D. S. Surry, S. L. Buchwald, Angew. Chem. Int. Ed. 2011, 50, 7312
15. C.-P. Zhang, D. A. Vicic, J. Am. Chem. Soc. 2012, 134, 183
16. Z. Weng, W. He, C. Chen, R. Lee, D. Tan, Z. Lai, D. Kong, Y. Yuan, K.-W. Huang, Angew. Chem. Int. Ed. 2013, 52, 1548
17. C. Chen, Y. Xie, L. Chu, R.-W. Wang, X. Zhang, F.-L. Qing, Angew. Chem. Int. Ed. 2012, 51, 2492
18. C.-P. Zhang, D. A. Vicic, Chem.–Asian J. 2012, 7, 1756
19. X. Shao, X. Wang, T. Yang, L. Lu, Q. Shen, Angew. Chem. Int. Ed. 2013, 52, 3457
20. L. D. Tran, I. Popov, O. Daugulis, J. Am. Chem. Soc. 2012, 134, 18240
21. A. Tlili, T. Billard, Angew. Chem. Int. Ed. 2013, 52, 6818
22. Y. Yang, X. Jiang, F.-L. Qing, J. Org. Chem. 2012, 77, 7538
23. A. Ferry, T. Billard, E. Bacqué, B. R. Langlois, J. Fluorine Chem. 2012, 134, 160
24. A. Ferry, T. Billard, B. R. Langlois, E. Bacqué, J. Org. Chem. 2008, 73, 9362
25. A. Ferry, T. Billard, B. R. Langlois, E. Bacqué, Angew. Chem. Int. Ed. 2009, 48, 8551
26. A. Ferry, T. Billard, B. R. Langlois, E. Bacqué, J. Org. Chem. 2008, 73, 9362
27. Y. Yang, X. Jiang, F.-L. Qing, J. Org. Chem. 2012, 77, 7538
28. J. Liu, L. Chu, F.-L. Qing, Org. Lett. 2013, 15, 894
29. S. Alazet, L. Zimmer, T. Billard, Angew. Chem. Int. Ed. 2013, 52, 10814
30. J. E. Saxton, Nat. Prod. Rep. 1997, 14, 559
31. M. Toyota, N. Ihara, Nat. Prod. Rep. 1998, 15, 327
32. J. A. Joule, Product Class 13: Indole and Its Derivatives, Thieme, Stuttgart, 2001
33. T. Kawasaki, K. Higuchi, Nat. Prod. Rep. 2005, 22, 761
34. G. R. Humphrey, J. T. Kuethe, Chem. Rev. 2006, 106, 2875
35. D. F. Taber, P. K. Tirunahari, Tetrahedron 2011, 67, 7195
36. G. Battistuzzi, S. Cacchi, G. Fabrizi, Eur. J. Org. Chem. 2002, 2671
37. R. C. Larock, Top. Organomet. Chem. 2005, 14, 147
38. S. Cacch, G. Fabrizi, Chem. Rev. 2011, 111, 215
39. R. Vicente, Org. Biomol. Chem. 2011, 9, 6469
40. M. Shiri, Chem. Rev. 2012, 112, 3508
41. S. Ye, J. Liu, J. Wu, Chem. Commun. 2012, 48, 5028
42. S. Ye, G. Liu, S. Pu, J. Wu, Org. Lett. 2012, 14, 70
43. L. Zhang, Q. Xiao, S. Ye, J. Wu, Chem.–Asian J. 2012, 7, 1909
44. Q. Xiao, J. Sheng, Z. Chen, J. Wu, Chem. Commun. 2013, 49, 8647
45. D. Yue, R. C. Larock, Org. Lett. 2004, 6, 1037
46. X. Feng, R. Kinjo, B. Donnadieu, G. Bertrand, Angew. Chem. Int. Ed. 2010, 49, 942
47. B. Yao, Q. Wang, J. Zhu, Angew. Chem. Int. Ed. 2012, 51, 5170
48. B. Yao, Q. Wang, J. Zhu, Angew. Chem. Int. Ed. 2012, 51, 12311
49. X.-F. Xia, N. Wang, L.-L. Zhang, X.-R. Song, X.-Y. Liu, Y.-M. Liang, J. Org. Chem. 2012, 77, 9163
50. X.-F. Xia, L.-L. Zhang, X.-R. Song, Y.-N. Niu, Y.-M. Liang, Chem. Commun. 2013, 49, 1410