Mechanistical insight into 'electrophilic' trifluoromethylation with S-(trifluoromethyl)dibenzothiophenium salts

Tetrahedron Letters

Volumn 51, Issue 41, 2010, Pages 5388-5391

  Macé, Yohan ^a   Pradet, Charlotte ^b   Popkin, Matthew ^b   Blazejewski, Jean Claude ^a   Magnier, Emmanuel ^a  

^a UNIVERSITÉ DE VERSAILLES SAINT QUENTIN EN YVELINES   (France)

^b GLAXOSMITHKLINE   (United Kingdom)

Author keywords

Mechanistic studies; Radical pathway; Sulfonium salts; Trifluoromethylation reaction

Indexed keywords

ANILINE; ENOL SILYL ETHER DERIVATIVE; NUCLEOPHILE; S (TRIFLUOROMETHYL)DIBENZOTHIOPHENIUM; SULFONIUM DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; SYNTHESIS;

EID: 79951808370     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.07.154     Document Type: Article

References (40)

1. J.T. Welch, and S. Eswarakrishnan Fluorine in Bioorganic Chemistry 1991 Wiley New York
2. R.E. Banks, B.E. Smart, and J.C. Tatlow J.C. Tatlow, Organofluorine Chemistry, Principles and Commercial Applications 1994 Plenum New York
3. J.-P. Bégué, and D. Bonnet-Delpon J. Fluorine Chem. 127 2006 992 1012
4. K.L. Kirk J Fluorine Chem. 127 2006 1013 1029
5. W.K. Hagmann J. Med. Chem. 51 2008 4359 4369
6. S. Purser, P.R. Moore, S. Swallowb, and V. Gouverneur Chem. Soc. Rev. 37 2008 320 330
7. T. Hiyama Organofluorine Compounds, Chemistry and Applications 2000 Springer Heidelberg, Berlin
8. P. Kirsch Modern Fluoroorganic Chemistry 2004 Wiley-VCH Weinheim
9. K. Uneyama Organofluorine Chemistry 2006 Blackwell Publishing Oxford
10. L.M. Yagupolskii, N.V. Kondratenko, and G.N. Timofeeva J. Org. Chem. USSR 20 1984 103 105
11. J.J. Yang, R.L. Kirchmeier, and J.M. Shreeve J. Org. Chem. 63 1998 2656 2660
12. L.M. Yagupol'skii, V.A. Matsnev, R.K. Orlova, B.G. Deryabkin, and Y.L. Yagupolskii J. Fluorine Chem. 129 2008 131 136
13. T. Umemoto, and S. Ishihara J. Am. Chem. Soc. 115 1993 2156 2164
14. P. Eisenberger, S. Gischig, and A. Togni Chem. Eur. J. 12 2006 2579 2586
15. I. Kieltsch, P. Eisenberger, and A. Togni Angew. Chem., Int. Ed. 46 2007 754 757
16. P. Eisenberger, I. Kieltsch, N. Armanino, and A. Togni Chem. Commun. 2008 1575 1577
17. K. Stanek, R. Koller, and A. Togni J. Org. Chem. 73 2008 7678 7685
18. R. Koller, K. Stanek, D. Stolz, R. Aardoom, K. Niedermann, and A. Togni Angew. Chem., Int. Ed. 48 2009 4332 4336
19. S. Noritake, N. Shibata, S. Nakumara, T. Toru, and M. Shiro Eur. J. Org. Chem. 20 2008 3465 3468
20. A. Matsnev, S. Noritake, Y. Nomura, E. Tokunaga, S. Nakamura, and N. Shibata Angew. Chem., Int. Ed. 49 2010 572 576
21. E. Magnier, J.-C. Blazejewski, M. Tordeux, and C. Wakselman Angew. Chem., Int. Ed. 45 2006 1279 1282
22. Y. Macé, B. Raymondeau, C. Pradet, J.-C. Blazejewski, and E. Magnier Eur. J. Org. Chem. 9 2009 1390 1397
23. Y. Macé, C. Urban, C. Pradet, J. Marrot, J.-C. Blazejewski, and E. Magnier Eur. J. Org. Chem. 19 2009 3150 3153
24. T. Ono, and T. Umemoto J. Fluorine Chem. 80 1996 163 166
25. Related nucleophilic attack was also proposed in the case of β-ketoester enolates see Ref. 10 and also Ref. 12.
26. J.-A. Ma, and D. Cahard J. Org. Chem. 68 2003 8726 8729
27. W.R. Dolbier Jr. Chem. Rev. 96 1996 1557 1584
28. W.R. Dolbier Jr. Organofluorine Chemistry: Fluorinated Alkenes and Reactive Intermediates R.D. Chambers, Topics in Current Chemistry Vol. 192 1997 Springer Berlin, Heidelberg 97 163
29. N.O. Brace J. Fluorine Chem. 93 1999 1 25
30. T. Umemoto, K. Adachi, and S. Ishihara J. Org. Chem. 72 2007 6905 6917
31. J.-C. Blazejewski, M.P. Wilmshurst, M.D. Popkin, C. Wakselman, G. Laurent, D. Nonclerq, A. Cleeren, Y. Ma, H.-S. Seo, and G. Leclercq Bioorg. Med. Chem. 11 2003 335 345
32. C. Wakselman, M. Tordeux, J.-L. Clavel, and B. Langlois J. Chem. Soc., Chem. Commun. 1991 993 994
33. J.-L. Clavel, B. Langlois, R. Nantermet, M. Tordeux, and C. Wakselman J. Chem. Soc., Perkin Trans. 1 1992 3371 3375
34. D. Cantacuzne, C. Wakselman, and R. Dorme J. Chem. Soc., Perkin Trans. 1 1977 1365 1371
35. C. Wakselman J. Fluorine Chem. 59 1992 367 378
36. 3O: C, 68.07; H, 6.07. Found: C, 67.87; H, 6.31.
37. M. Newcomb Tetrahedron 49 1993 1151 1176
38. 2 is very fast and supersedes cage escape and intramolecular radical cyclization.
39. R. Rathore, and J.K. Kochi J. Org. Chem. 61 1996 627 639
40. Personal communication of Dr. Andrew Douglas Phillips, University College of Dublin, Dublin, Ireland.