A facile and general route to 3-((trifluoromethyl)thio)benzofurans and 3-((trifluoromethyl)thio)benzothiophenes

Chemical Communications

Volumn 50, Issue 41, 2014, Pages 5494-5496

  Sheng, Jie ^a   Fan, Congbin ^a   Wu, Jie ^a,b  

^a FUDAN UNIVERSITY   (China)

^b SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

BENZOFURAN DERIVATIVE; BENZOTHIOPHENE; THIOPHENE DERIVATIVE; BENZENE DERIVATIVE; BENZOTHIOPHENE DERIVATIVE; BISMUTH DERIVATIVE; SULFANILAMIDE DERIVATIVE;

CHEMISTRY; SYNTHESIS; ARTICLE; CHEMICAL REACTION; ELECTROPHILICITY; NUCLEOPHILICITY;

BENZOFURANS; CHEMISTRY TECHNIQUES, SYNTHETIC; THIOPHENES;

EID: 84899571077     PISSN: 13597345     EISSN: 1364548X     Source Type: Journal    
DOI: 10.1039/c4cc01904k     Document Type: Article

References (87)

1. D. P. Walsh, Y.-T. Chang, Chem. Rev., 2006, 106, 2476
2. P. Arya, D. T. H. Chou, M.-G. Baek, Angew. Chem., Int. Ed., 2001, 40, 339
3. S. L. Schreiber, Science, 2000, 287, 1964
4. M. D. Burke, S. L. Schreiber, Angew. Chem., Int. Ed., 2004, 43, 46
5. S. L. Schreiber, Nature, 2009, 457, 153
6. D. S. Tan, Nat. Chem. Biol., 2005, 1, 74
7. C. Cordier, D. Morton, S. Murrison, A. Nelson, C. O'Leary-Steele, Nat. Prod. Rep., 2008, 25, 719
8. W. R. J. D. Galloway, A. I. Llobet, D. R. Spring, Nat. Commun., 2010, 1, 80
9. S. Oh, S. B. Park, Chem. Commun., 2011, 47, 12754
10. Y. Dong, D. Tang, N. Zhang, Y. Li, C. Zhang, L. Li, M. Li, Chem. Cent. J., 2013, 7, 124
11. J. R. Clem, D. K. Farver, J. R. Fischer, T. J. Johnson, Curr. Drug Saf., 2010, 5, 251
12. K. M. Zareba, Drugs Today, 2006, 42, 75
13. T. Ohtsuka, Y. Aoki, Drugs Future, 2003, 28, 143
14. S. O. Simonetti, E. L. Larghi, A. B. J. Bracca, T. S. Kaufman, Nat. Prod. Rep., 2013, 30, 941
15. M. V. Kulkarni, G. M. Kulkarni, C.-H. Lin, C.-M. Sun, Curr. Med. Chem., 2006, 13, 2795
16. S. Thareja, S. Aggarwal, T. R. Bhardwaj, M. Kumar, Med. Res. Rev., 2012, 32, 459
17. M. A. Musa, M. O. F. Khan, J. S. Cooperwood, Curr. Med. Chem., 2007, 14, 1249
18. A. S. Verkman, G. L. Lukacs, L. J. V. Galietta, Curr. Pharm. Des., 2006, 12, 2235
19. T. Fujita, S. Sanada, Y. Chiba, K. Sugiyama, J. Ichikawa, Org. Lett., 2014, 16, 1398
20. H.-S. Li, G. Liu, J. Org. Chem., 2014, 79, 509
21. W. Yuan, S. Ma, Org. Lett., 2014, 16, 193
22. X. Li, M.-H. Lin, Y. Han, F. Wang, J.-P. Cheng, Org. Lett., 2014, 16, 114
23. T. B. Grimaldi, D. F. Back, G. Zeni, J. Org. Chem., 2013, 78, 11017
24. S. Jana, J. D. Rainier, Org. Lett., 2013, 15, 4426
25. M. Yamaguchi, H. Katsumata, K. Manabe, J. Org. Chem., 2013, 78, 9270
26. S. Protti, M. Fagnoni, A. Albini, J. Org. Chem., 2012, 77, 6473
27. D.-H. Lee, K.-H. Kwon, C. S. Yi, J. Am. Chem. Soc., 2012, 134, 7325
28. Y. Liu, S. Ma, Org. Lett., 2012, 14, 720
29. L. Arias, Y. Vara, F. P. Cossio, J. Org. Chem., 2012, 77, 266
30. S.-H. Wang, P.-H. Li, L. Yu, L. Wang, Org. Lett., 2011, 13, 5968
31. D. A. Horton, G. T. Bourne, M. L. Smythe, Chem. Rev., 2003, 103, 893
32. Y. Nan, H. Miao, Z. Yang, Org. Lett., 2000, 2, 297
33. Y. Liao, J. Smith, R. Fathi, Z. Yang, Org. Lett., 2005, 7, 2707
34. Y. Liang, S. Tang, X.-D. Zhang, L.-Q. Mao, Y.-X. Xie, J.-H. Li, Org. Lett., 2006, 8, 3017
35. C. Martínez, R. Álvarez, J. M. Aurrecoechea, Org. Lett., 2009, 11, 1083
36. M. Nakamura, L. Ilies, S. Otsubo, Angew. Chem., Int. Ed., 2006, 45, 944
37. B. Wu, N. Yoshikai, Angew. Chem., Int. Ed., 2013, 52, 10496
38. H. Yu, M. Zhang, Y. Li, J. Org. Chem., 2013, 78, 8898
39. D. P. Hari, T. Hering, B. Koenig, Org. Lett., 2012, 14, 5334
40. L.-L. Sun, C.-L. Deng, R.-Y. Tang, X.-G. Zhang, J. Org. Chem., 2011, 76, 7546
41. M. Kuhn, F. C. Falk, J. Paradies, Org. Lett., 2011, 13, 4100
42. R. Filler and Y. Kobayashi, Biomedicinal Aspects of Fluorine Chemistry, Elsevier, Amsterdam, 1982
43. Fluorine in Bioorganic Chemistry, ed. J. T. Welch and S. Eswarakrishman, Wiley, New York, 1991
44. V. A. Petrov, Fluorinated Heterocyclic Compounds: Synthesis, Chemistry, and Applications, John Wiley & Sons, Inc., Hoboken, NJ, 2009
45. E. V. Nosova, G. N. Lipunova, V. N. Charushin, O. N. Chupakhin, J. Fluorine Chem., 2010, 131, 1267
46. S. Zhu, Y. Wang, W. Peng, L. Song, G. Jin, Curr. Org. Chem., 2002, 6, 1057
47. M. J. Silvester, Aldrichimica Acta, 1991, 24, 31
48. P. Kwiatkowski, T. D. Beeson, J. C. Conrad, D. W. C. MacMillan, J. Am. Chem. Soc., 2011, 133, 1738
49. Y. Kishi, H. Nagura, S. Inagi, T. Fuchigami, Chem. Commun., 2008, 3876
50. S. Fustero, S. Catalan, M. Sanchez-Rosello, A. Simon-Fuentes, C. del Pozo, Org. Lett., 2010, 12, 3484
51. T. Xu, G. Liu, Org. Lett., 2012, 14, 5416
52. Bioorganic and Medicinal Chemistry of Fluorine, ed. J.-P. Begue and D. Bonnet-Delpon, Wiley, Hoboken, 2008
53. C. Chen, L. Chu, F.-L. Qing, J. Am. Chem. Soc., 2012, 134, 12454
54. F. Baert, J. Colomb, T. Billard, Angew. Chem., Int. Ed., 2012, 51, 10382
55. G. Teverovskiy, D. S. Surry, S. L. Buchwald, Angew. Chem., Int. Ed., 2011, 50, 7312
56. C.-P. Zhang, D. A. Vicic, J. Am. Chem. Soc., 2012, 134, 183
57. 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
58. C. Chen, Y. Xie, L. Chu, R.-W. Wang, X. Zhang, F.-L. Qing, Angew. Chem., Int. Ed., 2012, 51, 2492
59. C.-P. Zhang, D. A. Vicic, Chem. - Asian J., 2012, 7, 1756
60. X. Shao, X. Wang, T. Yang, L. Lu, Q. Shen, Angew. Chem., Int. Ed., 2013, 52, 3457
61. L. D. Tran, I. Popov, O. Daugulis, J. Am. Chem. Soc., 2012, 134, 18240
62. D. C. Remy, K. E. Rittle, C. A. Hunt, M. B. Freedman, J. Org. Chem., 1976, 41, 1644
63. D. J. Adams, A. Goddard, J. H. Clark, D. J. Macquarrie, Chem. Commun., 2000, 987
64. O. A. Tomashenko, V. V. Grushin, Chem. Rev., 2011, 111, 4475
65. K. P. Wang, S. Y. Yun, P. Mamidipalli, D. Lee, Chem. Sci., 2013, 4, 3205
66. M. Rueping, N. Tolstoluzhsky, P. Nikolaienko, Chem. - Eur. J., 2013, 19, 14043
67. Y. D. Yang, A. Azuma, E. Tokunaga, M. Yamasaki, M. Shiro, N. Shibata, J. Am. Chem. Soc., 2013, 135, 8782
68. A. Tlili, T. Billard, Angew. Chem., Int. Ed., 2013, 52, 6818
69. Y. Yang, X. Jiang, F.-L. Qing, J. Org. Chem., 2012, 77, 7538
70. A. Ferry, T. Billard, E. Bacqué, B. R. Langlois, J. Fluorine Chem., 2012, 134, 160
71. A. Ferry, T. Billard, B. R. Langlois, E. Bacqué, J. Org. Chem., 2008, 73, 9362
72. A. Ferry, T. Billard, B. R. Langlois, E. Bacqué, Angew. Chem., Int. Ed., 2009, 48, 8551
73. T. Bootwicha, X. Liu, R. Pluta, I. Atodiresei, M. Rueping, Angew. Chem., Int. Ed., 2013, 52, 12856
74. A. Ferry, T. Billard, E. Bacqué, B. R. Langlois, J. Fluorine Chem., 2012, 134, 160
75. Y. Yang, X. Jiang, F.-L. Qing, J. Org. Chem., 2012, 77, 7538
76. J. Liu, L. Chu, F.-L. Qing, Org. Lett., 2013, 15, 894
77. W. A. Sheppard, J. Org. Chem., 1964, 29, 895
78. S. Alazet, L. Zimmer, T. Billard, Angew. Chem., Int. Ed., 2013, 52, 10814
79. D. Enders, C. Grondal, M. R. M. Hüttl, Angew. Chem., Int. Ed., 2007, 46, 1570
80. X. Wang, T. Yang, X. Cheng, Q. Shen, Angew. Chem., Int. Ed., 2013, 52, 12860
81. Q. H. Deng, C. Rettenmeier, H. Wadepohl, L. H. Gade, Chem. - Eur. J., 2014, 20, 93
82. S. Munavalli, D. K. Rohrbaugh, D. I. Rossman, F. J. Berg, G. W. Wagner, H. D. Durst, Synth. Commun., 2000, 30, 2847
83. J. Sheng, S. Li, J. Wu, Chem. Commun., 2014, 50, 578
84. Q. Xiao, J. Sheng, Z. Chen, J. Wu, Chem. Commun., 2013, 49, 8647
85. Q. Xiao, J. Sheng, Q. Ding, J. Wu, Eur. J. Org. Chem., 2014, 217
86. R. Pluta, P. Nikolaienko, M. Rueping, Angew. Chem., Int. Ed., 2014, 53, 1650
87. M. Rueping, X. Liu, T. Bootwicha, R. Pluta, C. Merkens, Chem. Commun., 2014, 50, 2508