Hypervalent iodine mediated para -selective fluorination of anilides

Journal of Organic Chemistry

Volumn 78, Issue 2, 2013, Pages 728-732

  Tian, Tian ^a   Zhong, Wen He ^a   Meng, Shuai ^a   Meng, Xiang Bao ^a   Li, Zhong Jun ^a  

^a PEKING UNIVERSITY HEALTH SCIENCE CENTER   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ANILIDES; FACILE ACCESS; HYPERVALENT IODINE; IODOBENZENE; OPERATIONAL SAFETY; REGIO-SELECTIVE; SELECTIVE FLUORINATION;

FLUORINATION; FLUORINE; HALOGENATION; IODINE;

AMIDES;

ANILIDE; BIS(TERT BUTYLCARBONYLOXY) IODOBENZENE; HYDROFLUORIC ACID; IODINE; IODOBENZENE; PYRIDINE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; FLUORINATION;

ANILIDES; HALOGENATION; HYDROFLUORIC ACID; IODINE; IODOBENZENES; MOLECULAR STRUCTURE; PYRIDINES;

EID: 84872551502     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo302099d     Document Type: Article

References (50)

1. Müller, K.; Faeh, C.; Diederich, F. Science 2007, 317, 1881
2. Fluorine and Health: Molecular Imaging, Biomedical Materials and Pharmaceuticals; Tressaud, A.; Haufe, G., Eds.; Elsevier Science: Amsterdam, 2008.
3. Banks, R. E; Mohialdin-Khaffaf, S. N.; Lal, G. S.; Sharif, I.; Syvret, R. G. J. Chem. Soc., Chem. Commun. 1992, 595
4. Jahnisch, K.; Baerns, M.; Hessel, V.; Ehrfeld, W.; Haverkamp, V.; Lowe, H.; Wille, C.; Guber, A. J. Fluorine Chem. 2000, 105, 117
5. Chambers, R. D. Fluorine in Organic Chemistry; Oxford: New York, 2004.
6. Furuya, T.; Kuttruff, C. A.; Ritter, T. Curr. Opin. Drug Discovery Dev. 2008, 11, 803
7. Karam, O.; Jacquesy, J. C.; Jouannetaud, M. P. Tetrahedron Lett. 1994, 35, 2541
8. Stavber, S.; Jereb, M.; Zupan, M. Synlett 1999, 9, 1375
9. Nyffeler, P. T.; Durón, S. G.; Burkart, M. D.; Vincent, S. P.; Wong, C. H. Angew. Chem., Int. Ed. 2005, 44, 192
10. Balz, G.; Schiemann, G. Ber. Deutsch. Chem. Ges. 1927, 60, 1186
11. Swain, C. G.; Rogers, R. J. J. Am. Chem. Soc. 1975, 97, 799
12. Adams, D. J.; Clark, J. H. Chem. Soc. Rev. 1999, 28, 225
13. Sandford, G. J. Fluorine Chem. 2007, 128, 90
14. Horwitz, J. P.; Tomson, A. J. J. Org. Chem. 1961, 26, 3392
15. Barlin, G. B.; Young, A. C. J. Chem. Soc., Perkin Trans. 1 1972, 1269
16. Pike, V. W.; Aigbirhio, F. I. J. Chem. Soc., Chem. Commun. 1995, 21, 2215
17. Shah, A.; Pike, V. W.; Widdowson, D. A. J. Chem. Soc., Perkin Trans. 1 1998, 2043
18. Yamada, S.; Gavryushin, A.; Knochel, P. Angew. Chem., Int. Ed. 2010, 49, 2215
19. Stille, J. K.; Lau, K. S. Y. Acc. Chem. Res. 1977, 10, 434
20. Differding, E.; Wehrli, M. Tetrahedron Lett. 1991, 32, 3819
21. Lal, G. S. J. Org. Chem. 1993, 58, 2791
22. Hull, K. L.; Anani, W. Q.; Sanford, M. S. J. Am. Chem. Soc. 2006, 128, 7134
23. Furuya, T.; Ritter, T. J. Am. Chem. Soc. 2008, 130, 10060
24. Kaspi, A. W.; Yahav-Levi, A.; Goldberg, I.; Vigalok, A. Inorg. Chem. 2008, 47, 5
25. Furuya, T.; Strom, A. E.; Ritter, T. J. Am. Chem. Soc. 2009, 131, 1662
26. Furuya, T.; Ritter, T. Org. Lett. 2009, 11, 2860
27. Cairns, M. A.; Dixon, K. R.; McFarland, J. J. J. Chem. Soc., Dalton Trans. 1975, 1159
28. Stille, J. K.; Lau, K. S. Y. Acc. Chem. Res. 1977, 10, 434
29. Grushin, V. V. Chem.-Eur. J. 2002, 8, 1006
30. Wirth, T. Angew. Chem., Int. Ed. 2005, 44, 3656
31. Richardson, R. D.; Wirth, T. Angew. Chem., Int. Ed. 2006, 45, 4402
32. Uyanik, M.; Ishihara, K. Chem. Commun. 2009, 2086
33. Pouységu, L.; Deffieux, D.; Quideau, S. Tetrahedron 2010, 66, 2235
34. Zhdankin, V. V. J. Org. Chem. 2011, 76, 1185
35. Itoh, N.; Sakamoto, T.; Miyazawa, E.; Kikugawa, Y. J. Org. Chem. 2002, 67, 7424
36. Liu, H.; Wang, X.; Gu, Y. Org. Biomol. Chem. 2011, 9, 1614
37. Liu, H.; Xie, Y.; Gu, Y. Tetrahedron Lett. 2011, 52, 4324
38. Kitamura, T.; Kuriki, S.; Morshed, M. H.; Hori, Y. Org. Lett. 2011, 13, 2392
39. Saito, M.; Miyamoto, K.; Ochiai, M. Chem. Commun. 2011, 47, 3410
40. Gao, Z.; Lim, Y. H.; Tredwell, M.; Li, L.; Verhoog, S.; Hopkinson, M.; Kaluza, W.; Collier, T. L.; Passchier, J.; Huiban, M.; Gouverneur, V. Angew. Chem., Int. Ed. 2012, 51, 6733
41. Zhong, W.; Yang, J.; Meng, X.; Li, Z. J. Org. Chem. 2011, 76, 9997
42. Zhong, W.; Liu, S.; Yang, J.; Meng, X.; Li, Z. Org. Lett. 2012, 14, 3336
43. Tang, P.; Ritter, T. Tetrahedron 2011, 67, 4449
44. Fier, P. S.; Hartwig, J. F. J. Am. Chem. Soc. 2012, 134, 10795
45. Salazar, J.; Lopez, S. E.; Rebollo, O. J. Fluorine Chem. 2003, 124, 111
46. Xiao, F.; Liu, Y.; Tang, C.; Deng, G. J. Org. Lett. 2012, 14, 984
47. Waisser, K.; Kuneš, J.; Roman, M.; Buděší nský, M.; Exner, O. Phosphorus, Sulfur Silicon Relat. Elem. 1994, 97, 71
48. Gonec, T.; Bobal, P.; Sujan, J.; Pavlacka, L.; Vesely, L.; Kreckova, E.; Kos, J.; Jampilek, J.; Pesko, M.; Guo, J.; Coffey, A.; Kralova, K.; Kollar, P.; Imramovsky, A.; Placek, L. Molecules 2012, 17, 613
49. Gilday, J. P.; Negri, J. T.; Widdowson, D. A. Tetrahedron 1989, 45, 4605
50. Shimizu, Y.; Morimoto, H.; Zhang, M.; Ohshima, T. Angew. Chem., Int. Ed. 2012, 51, 8564