Copper-catalyzed regioselective trifluoromethylthiolation of pyrroles by trifluoromethanesulfonyl hypervalent iodonium ylide

Organic Letters

Volumn 17, Issue 5, 2015, Pages 1094-1097

  Huang, Zhongyan ^a   Yang, Yu Dong ^a   Tokunaga, Etsuko ^a   Shibata, Norio ^a  

^a NAGOYA INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84924257391     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol503616y     Document Type: Article

References (66)

1. Kirsch, P. Modern Fluoroorganic Chemistry: Synthesis, Reactivity, Applications; Wiley-VCH: Weinheim, Germany, 2004.
2. Hiyama, T. Organofluorine Compounds: Chemistry and Properties; Springer: Berlin, 2000.
3. Uneyama, K. Organofluorine Chemistry; Blackwell: Oxford, U.K., 2006.
4. Banks, R. E., Smart, B. E., and Tatlow, J. C. Organofluorine Chemistry: Principles and Commercial Applications; Plenum Press: New York, 1994.
5. O-Hagan, D. Chem. Soc. Rev. 2008, 37, 308
6. Wang, J.; Sánchez-Roselló, M.; Aceña, J. L.; Pozo, C.; Sorochinsky, A. E.; Fustero, S.; Soloshonok, V. A.; Liu, H. Chem. Rev. 2014, 114, 2432
7. Boiko, V. N. Beilstein J. Org. Chem. 2010, 6, 880
8. Landelle, G.; Panossian, A.; Pazenok, S.; Vors, J.-P.; Leroux, F. R. Beilstein J. Org. Chem. 2013, 9, 2476
9. Thili, A.; Billard, T. Angew. Chem., Int. Ed. 2013, 52, 6818
10. Liang, T.; Neumann, C. N.; Ritter, T. Angew. Chem., Int. Ed. 2013, 52, 8214
11. Toulgoat, F.; Alazet, S.; Billard, T. Eur. J. Org. Chem. 2014, 2415
12. Zhu, W.; Wang, J.; Wang, S.; Gu, Z.; Acena, J. L.; Izawa, K.; Liu, H.; Soloshonok, V. A. J. Fluorine Chem. 2014, 167, 37
13. Xu, X.-H.; Matsuzaki, K.; Shibata, N. Chem. Rev. 2015, 115, 731
14. Ferry, A.; Billard, T.; Langlois, B. R.; Bacqué, E. Angew. Chem., Int. Ed. 2009, 48, 8551
15. Chen, C.; Chu, L.; Qing, F.-L. J. Am. Chem. Soc. 2012, 134, 12454
16. Chen, C.; Xie, Y.; Chu, L.; Wang, R.-W.; Zhang, X.; Qing, F.-L. Angew. Chem., Int. Ed. 2012, 51, 10
17. Alazet, S.; Zimmer, L.; Billard, T. Angew. Chem., Int. Ed. 2013, 52, 10814
18. Alazet, S.; Ollivier, K.; Billard, T. Beilstein J. Org. Chem. 2013, 9, 2354
19. Deng, Q.-H.; Rettenmeier, C.; Wadepohl, H.; Gade, L. H. Chem.-Eur. J. 2014, 20, 93
20. Vinogradova, E. V.; Müller, P.; Buchwald, S. L. Angew. Chem., Int. Ed. 2014, 53, 3125
21. Zhu, S.-Q.; Xu, X.-H.; Qing, F.-L. Eur. J. Org. Chem. 2014, 4453
22. Scherer, O. Angew. Chem. 1939, 52, 457
23. Nodiff, E. A.; Lipschutz, S.; Craig, P. N.; Gordon, M. J. Org. Chem. 1960, 25, 60
24. Kremsner, J. M.; Rack, M.; Pilger, C.; Kappe, C. O. Tetrahedron Lett. 2009, 50, 3665
25. Wakselman, C.; Tordeux, M. J. Chem. Soc. Commun. 1984, 793
26. Soloshonok, V.; Kukhar, V.; Pustovit, Y.; Nazaretian, V. Synlett 1992, 657
27. Kieltsch, I.; Eisenberger, P.; Togni, A. Angew. Chem., Int. Ed. 2007, 46, 754
28. Capone, S.; Kieltsch, I.; Flögel, O.; Lelais, G.; Togni, A.; Seebach, D. Helv. Chim. Acta 2008, 91, 2035
29. Ausín, C.; Kauffman, J. S.; Duff, R. J.; Shivaprasad, S.; Beaucage, S. L. Tetrahedron 2010, 66, 68
30. Yasui, H.; Yamamoto, T.; Tokunaga, E.; Shibata, N. J. Fluorine Chem. 2011, 132, 186
31. Man, E. H.; Coffman, D. D.; Muetterties, E. L. J. Am. Chem. Soc. 1959, 81, 3575
32. Andreades, S.; Harris, J. F.; Sheppard, W. A. J. Org. Chem. 1964, 29, 898
33. Hanack, M.; Kühnle, A. Tetrahedron Lett. 1981, 22, 3047
34. Kolasa, A. J. Fluorine Chem. 1987, 36, 29
35. Popov, V. I.; Haas, A.; Lieb, M. J. Fluorine Chem. 1990, 47, 131
36. Adams, D. J.; Clark, J. H. J. Org. Chem. 2000, 65, 1456
37. Adams, D. J.; Goddard, A.; Clark, J. H.; Macquarrie, D. J. Chem. Commun. 2000, 987
38. Teverovskiy, G.; Surry, D. S.; Buchwald, S. L. Angew. Chem., Int. Ed. 2011, 50, 7312
39. Zhang, C.-P.; Vivic, D. A. J. Am. Chem. Soc. 2012, 134, 183
40. Weng, Z.; He, W.; Chen, C.; Lee, R.; Tan, D.; Lai, Z.; Kong, D.; Yuan, Y.; Huang, K.-W. Angew. Chem., Int. Ed. 2013, 52, 1548
41. Rueping, M.; Tolstoluzhsky, N.; Nikolaienko, P. Chem.-Eur. J. 2013, 19, 14043
42. Pluta, R.; Nikolaienko, P.; Rueping, M. Angew. Chem., Int. Ed. 2014, 53, 1650
43. Xu, C.; Shen, Q. Org. Lett. 2014, 16, 2046
44. Kang, K.; Xu, C.; Shen, Q. Org. Chem. Front. 2014, 1, 294
45. Hu, F.; Shao, X.; Zhu, D.; Lu, L.; Shen, Q. Angew. Chem., Int. Ed. 2014, 53, 6105
46. Baert, F.; Colomb, J.; Billard, T. Angew. Chem., Int. Ed. 2012, 51, 10382
47. Alazet, S.; Zimmer, L.; Billard, T. Angew. Chem., Int. Ed. 2013, 52, 10814
48. Shao, X.; Wang, X.; Yang, T.; Lu, L.; Shen, Q. Angew. Chem., Int. Ed. 2013, 52, 3457
49. Wang, X.; Yang, T.; Cheng, X.; Shen, Q. Angew. Chem., Int. Ed. 2013, 52, 12860
50. Bootwicha, T.; Liu, X.; Pluta, R.; Atodiresei, I.; Rueping, M. Angew. Chem., Int. Ed. 2013, 52, 12856
51. Xu, C.; Ma, B.; Shen, Q. Angew. Chem., Int. Ed. 2014, 53, 9316
52. Alazet, S.; Zimmer, L.; Billard, T. Chem.-Eur. J. 2014, 20, 8589
53. Yang, Y.-D.; Azuma, A.; Tokunaga, E.; Yamasaki, M.; Shiro, M.; Shibata, N. J. Am. Chem. Soc. 2013, 135, 8782
54. d-Ischia, M.; Napolitano, A.; Pezzella, A. In Comprehensive Heterocyclic Chemistry III: Pyrroles and Their Benzo Derivatives: Applications, Vol. 3; Katritzky, A. R.; Ramsden, C. A.; Scriven, E. F. V.; Taylor, R. J. K., Eds.; Elsevier: Amsterdam, 2008; pp 353-388.
55. Young, I. S.; Thornton, P. D.; Thompson, A. Nat. Prod. Rep. 2010, 27, 1801
56. Xin, X.; Wang, D.; Li, X.; Wan, B. Angew. Chem., Int. Ed. 2012, 51, 1693
57. Michlik, S.; Kempe, R. Nat. Chem. 2013, 5, 140
58. Komatsubara, M.; Umeki, T.; Fukuda, T.; Iwao, M. J. Org. Chem. 2014, 79, 529
59. Estévez, V.; Villacampa, M.; Menéndez, J. C. Chem. Soc. Rev. 2014, 43, 4633
60. Haas, A.; Niemann, U. Chem. Ber. 1977, 110, 67
61. Dorn, S.; Eggenbeg, P.; Gerstenberger, M. R. C.; Haas, A.; Niemann, U.; Zobrist, P. Helv. Chim. Acta 1979, 62, 1442
62. Gerstenberger, M. R. C.; Haas, A.; Liebig, F. J. Fluorine Chem. 1982, 19, 461
63. Bélanger, P. C.; Atkinson, J. G.; Rooney, C. S.; Britcher, S. F.; Remy, D. C. J. Org. Chem. 1983, 48, 3234
64. Ferry, A.; Billard, T.; Bacqué, E.; Langlois, B. R. J. Fluorine Chem. 2012, 134, 160
65. Pang, W.; Zhu, S.; Xing, C.; Luo, N.; Jiang, H.; Zhu, S. J. Fluorine Chem. 2008, 129, 343
66. Dolbier, W. R. Guide to Fluorine NMR for Organic Chemists; John Wiley & Sons: Hoboken, New Jersey, USA, 2009.