Synthesis of Billard-Langlois Reagents and their Derivatives by Copper-Catalyzed N-Trifluoromethylthiolation of Arylamines with a Trifluoromethanesulfonyl Hypervalent Iodonium Ylide

Asian Journal of Organic Chemistry

Volumn 4, Issue 6, 2015, Pages 525-527

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

^a NAGOYA INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

Arylamines; Copper; Hypervalent iodine; Trifluoromethanesulfenamides; Trifluoromethylthiolation

Indexed keywords

EID: 84930177794     PISSN: 21935807     EISSN: None     Source Type: Journal    
DOI: 10.1002/ajoc.201500067     Document Type: Article

References (53)

1. R. E. Banks, B. E. Smart, J. C. Tatlow, Organofluorine Chemistry: Principles and Commercial Applications, Plenum Press, New York, 1994;
2. T. Hiyama, Organofluorine Compounds: Chemistry and Properties, Springer, Berlin, 2000;
3. P. Kirsch, Modern Fluoroorganic Chemistry: Synthesis Reactivity, Applications, Wiley-VCH, Weinheim, Germany, 2004;
4. K. Uneyama, Organofluorine Chemistry, Blackwell, Oxford, U.K., 2006;
5. D. Ohagan, Chem. Soc. Rev. 2008, 37, 308-319;
6. J. Wang, M. Sánchez-Roselló, J. L. Aceña, C. Pozo, A. E. Sorochinsky, S. Fustero, V. A. Soloshonok, H. Liu, Chem. Rev. 2014, 114, 2432-2506.
7. V. N. Boiko, Beilstein J. Org. Chem. 2010, 6, 880-921;
8. G. Landelle, A. Panossian, S. Pazenok, J.-P. Vors, F. R. Leroux, Beilstein J. Org. Chem. 2013, 9, 2476-2536;
9. A. Tlili, T. Billard, Angew. Chem. Int. Ed. 2013, 52, 6818-6819; Angew. Chem. 2013, 125, 6952-6954;
10. T. Liang, C. N. Neumann, T. Ritter, Angew. Chem. Int. Ed. 2013, 52, 8214-8264; Angew. Chem. 2013, 125, 8372-8423;
11. F. Toulgoat, S. Alazet, T. Billard, Eur. J. Org. Chem. 2014, 2415-2428;
12. W. Zhu, J. Wang, S. Wang, Z. Gu, J. L. Acena, K. Izawa, H. Liu, V. A. Soloshonok, J. Fluorine Chem. 2014, 167, 37-54;
13. X.-H. Xu, K. Matsuzaki, N. Shibata, Chem. Rev. 2015, 115, 731-764.
14. O. Scherer, Angew. Chem. 1939, 52, 457-459;
15. E. H. Man, D. D. Coffman, E. L. Muetterties, J. Am. Chem. Soc. 1959, 81, 3575-3577;
16. E. A. Nodiff, S. Lipschutz, P. N. Craig, M. Gordon, J. Org. Chem. 1960, 25, 60-65;
17. S. Andreades, J. F. Harris, Jr., W. A. Sheppard, J. Org. Chem. 1964, 29, 898-900;
18. M. Hanack, A. Kühnle, Tetrahedron Lett. 1981, 22, 3047-3048;
19. C. Wakselman, M. Tordeux, J. Chem. Soc. Chem. Commun. 1984, 793-794;
20. A. Kolasa, J. Fluorine Chem. 1987, 36, 29-40;
21. V. I. Popov, A. Haas, M. Lieb, J. Fluorine Chem. 1990, 47, 131-136;
22. V. Soloshonok, V. Kukhar, Y. Pustovit, V. Nazaretian, Synlett 1992, 657-658;
23. D. J. Adams, J. H. Clark, J. Org. Chem. 2000, 65, 1456-1460;
24. D. J. Adams, A. Goddard, J. H. Clark, D. J. Macquarrie, Chem. Commun. 2000, 987-988;
25. J. M. Kremsner, M. Rack, C. Pilger, C. O. Kappe, Tetrahedron Lett. 2009, 50, 3665-3668.
26. G. Teverovskiy, D. S. Surry, S. L. Buchwald, Angew. Chem. Int. Ed. 2011, 50, 7312-7314; Angew. Chem. 2011, 123, 7450-7452;
27. C.-P. Zhang, D. A. Vivic, J. Am. Chem. Soc. 2012, 134, 183-185;
28. 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, 1548-1552; Angew. Chem. 2013, 125, 1588-1592.
29. S. Munavalli, D. K. Rohrbaugh, D. I. Rossman, F. J. Berg, G. W. Wagner, H. D. Durst, Synth. Commun. 2000, 30, 2847-2854;
30. F. Baert, J. Colomb, T. Billard, Angew. Chem. Int. Ed. 2012, 51, 10382-10385; Angew. Chem. 2012, 124, 10528-10531;
31. S. Alazet, L. Zimmer, T. Billard, Angew. Chem. Int. Ed. 2013, 52, 10814-10817; Angew. Chem. 2013, 125, 11014-11017;
32. X. Shao, X. Wang, T. Yang, L. Lu, Q. Shen, Angew. Chem. Int. Ed. 2013, 52, 3457-3460; Angew. Chem. 2013, 125, 3541-3544;
33. X. Wang, T. Yang, X. Cheng, Q. Shen, Angew. Chem. Int. Ed. 2013, 52, 12860-12864; Angew. Chem. 2013, 125, 13098-13102;
34. T. Bootwicha, X. Liu, R. Pluta, I. Atodiresei, M. Rueping, Angew. Chem. Int. Ed. 2013, 52, 12856-12859; Angew. Chem. 2013, 125, 13093-13097;
35. M. Rueping, N. Tolstoluzhsky, P. Nikolaienko, Chem. Eur. J. 2013, 19, 14043-14046;
36. R. Pluta, P. Nikolaienko, M. Rueping, Angew. Chem. Int. Ed. 2014, 53, 1650-1653; Angew. Chem. 2014, 126, 1676-1679;
37. F. Hu, X. Shao, D. Zhu, L. Lu, Q. Shen, Angew. Chem. Int. Ed. 2014, 53, 6105-6109; Angew. Chem. 2014, 126, 6219-6223;
38. C. Xu, B. Ma, Q. Shen, Angew. Chem. Int. Ed. 2014, 53, 9316-9320; Angew. Chem. 2014, 126, 9470-9474;
39. C. Xu, Q. Shen, Org. Lett. 2014, 16, 2046-2049;
40. K. Kang, C. Xu, Q. Shen, Org. Chem. Front. 2014, 1, 294-297;
41. S. Alazet, L. Zimmer, T. Billard, Chem. Eur. J. 2014, 20, 8589-8593.
42. Y.-D. Yang, A. Azuma, E. Tokunaga, M. Yamasaki, M. Shiro, N. Shibata, J. Am. Chem. Soc. 2013, 135, 8782-8785;
43. TCI America, http://www.tcichemicals.com/en/us/product/tci-topics/ArticleHighlights_20141201.html (Checked, 2015/03/11); http://www.synquestlabs.com/product/id/98242.html; SynQuest Laboratories, http://www.synquestlabs.com/product/id/98242.html (Checked, 2015/03/11);
44. Z. Huang, Y.-D. Yang, E. Tokunaga, N. Shibata, Org. Lett. 2015, 17, 1094-1097;
45. A. Arimori, M. Takada, N. Shibata, Org. Lett. 2015, 17, 1063-1065.
46. A. Ferry, T. Billard, B. R. Langlois, E. Bacque, Angew. Chem. Int. Ed. 2009, 48, 8551-8555; Angew. Chem. 2009, 121, 8703-8707;
47. A. Ferry, T. Billard, E. Bacqué, B. R. Langlois, J. Fluorine Chem. 2012, 134, 160-163;
48. Q. Xiao, J. Sheng, Z. Chen, J. Wu, Chem. Commun. 2013, 49, 8647-8649;
49. S. Alazet, K. Ollivier, T. Billard, Beilstein J. Org. Chem. 2013, 9, 2354-2357;
50. J. Sheng, S. Li, J. Wu, Chem. Commun. 2014, 50, 578-580;
51. J. Liu, L. Chu, F.-L. Qing, Org. Lett. 2013, 15, 894-897.
52. A. Ferry, T. Billard, B. R. Langlois, E. Bacque, J. Org. Chem. 2008, 73, 9362-9365.
53. A. Ferry, New Reactivity of DAST and its Analogs: Synthesis and Applications of Fluorinated Sulfinamidines and Sulfanylamines. Ph.D. Thesis, University of Lyon, Lyon, France, 2007.