First and second generation of trifluoromethanesulfenamide reagent: A trifluoromethylthiolating comparison

Journal of Fluorine Chemistry

Volumn 179, Issue , 2015, Pages 89-95

  Glenadel, Quentin ^a   Alazet, Sébastien ^a   Billard, Thierry ^a,b  

^a UNIVERSITÉ LYON 1   (France)

^b CERMEP IMAGERIE DU VIVANT   (France)

Author keywords

Alkynes; Aromatic; Ketones; Trifluoromethanesulfenamide; Trifluoromethylthiolation

Indexed keywords

EID: 84946471862     PISSN: 00221139     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jfluchem.2015.06.007     Document Type: Article

References (42)

1. H. Moissan C.R. Hebd. Seances Acad. Sci. 128 1899 1543
2. A. Becker Inventory of Industrial Fluoro-biochemicals 1996 Eyrolles Paris
3. M. Hird Chem. Soc. Rev. 36 2007 2070 2095
4. T. Hiyama Organofluorine Compounds: Chemistry and Applications 2000 Springer Berlin/Heidelberg
5. P. Kirsch Modern Fluoroorganic Chemistry: Synthesis, Reactivity, Applications 2013 Wiley Wheineim
6. I. Ojima Fluorine in Medicinal Chemistry and Chemical Biology 2009 Wiley Chichester
7. J.-P. Begue, and D. Bonnet-Delpon Bioorganic and Medicinal Chemistry of Fluorine 2008 John Wiley & Sons, Inc Hoboken, NJ
8. W.K. Hagmann J. Med. Chem. 51 2008 4359 4369
9. P. Jeschke ChemBioChem 5 2004 570 589
10. B.R. Langlois, T. Billard, S. Large, and N. Roques Fluorinated bioactive compounds in the agricultural & medical fields 1999 Chemical & Polymer Hemel Hempstead 24/21 24/24
11. K. Muller, C. Faeh, and F. Diederich Science 317 2007 1881 1886
12. S. Purser, P.R. Moore, S. Swallow, and V. Gouverneur Chem. Soc. Rev. 37 2008 320 330
13. C. Hansch, A. Leo, and R.W. Taft Chem. Rev. 91 1991 165 195
14. A. Avdeef Absorption and Drug Development: Solubility, Permeability, and Charge State 2012 Wiley Hoboken, NJ
15. D.E. Clark Drug Discovery Today 8 2003 927 933
16. J. Kelder, P.D.J. Grootenhuis, D.M. Bayada, L.P.C. Delbressine, and J.-P. Ploemen Pharm. Res. 16 1999 1514 1519
17. U. Norinder, and M. Haeberlein Adv. Drug Del. Rev. 54 2002 291 313
18. D.A. Smith, C. Allerton, H. Kubinyi, H. Walker, D.K. Walker, R. Mannhold, and G. Folkers Pharmacokinetics and Metabolism in Drug Design 2012 Wiley Weinheim
19. F. Toulgoat, S. Alazet, and T. Billard Eur. J. Org. Chem. 2014 2415 2428
20. X.-H. Xu, K. Matsuzaki, and N. Shibata Chem. Rev. 115 2015 731 764
21. V.N. Boiko Beilstein J. Org. Chem. 6 2010 880 921
22. G. Landelle, A. Panossian, S. Pazenok, J.-P. Vors, and F.R. Leroux Beilstein J. Org. Chem. 9 2013 2476 2536
23. A. Tlili, and T. Billard Angew. Chem. 125 2013 6952 6954
24. T. Billard Encyclopedia of Reagents for Organic Synthesis [Online] 2015 John Wiley & Sons Ltd 10.1002/047084289X.rn01828
25. T. Billard Encyclopedia of Reagents for Organic Synthesis [Online] 2014 John Wiley & Sons Ltd 10.1002/047084289X.rn01763
26. X. Shao, X. Wang, T. Yang, L. Lu, and Q. Shen Angew. Chem. Int. Ed. 52 2013 3457 3460
27. X. Shao, C. Xu, L. Lu, and Q. Shen J. Org. Chem. 80 2015 3012 3021
28. T. Bootwicha, X. Liu, R. Pluta, I. Atodiresei, and M. Rueping Angew. Chem. Int. Ed. 52 2013 12856 12859
29. S. Alazet, L. Zimmer, and T. Billard Chem. Eur. J. 20 2014 8589 8593
30. C. Xu, B. Ma, and Q. Shen Angew. Chem. Int. Ed. 53 2014 9316 9320
31. E.C. Stump Chem. Eng. News 45 1967 44
32. A. Ferry, T. Billard, B.R. Langlois, and E. Bacqué Angew. Chem. Int. Ed. 48 2009 8551 8555
33. A. Ferry, T. Billard, E. Bacqué, and B.R. Langlois J. Fluorine Chem. 134 2012 160 163
34. F. Baert, J. Colomb, and T. Billard Angew. Chem. Int. Ed. 51 2012 10382 10385
35. S. Alazet, L. Zimmer, and T. Billard Angew. Chem. Int. Ed. 52 2013 10814 10817
36. S. Alazet, K. Ollivier, and T. Billard Beilstein J. Org. Chem. 9 2013 2354 2357
37. S. Alazet, L. Zimmer, and T. Billard J. Fluorine Chem. 171 2015 78 81
38. S. Alazet, and T. Billard Synlett 26 2015 76 78
39. S. Alazet, E. Ismalaj, Q. Glenadel, and T. Billard Eur. J. Org. Chem. 2015 (in press)
40. C. Chen, X.-H. Xu, B. Yang, and F.-L. Qing Org. Lett. 16 2014 3372 3375
41. S.-G. Li, and S.Z. Zard Org. Lett. 15 2013 5898 5901
42. A. Ferry, T. Billard, B.R. Langlois, and E. Bacque J. Org. Chem. 73 2008 9362 9365