Polyfluoroalkylation of carbonyl compounds by polyfluoroalkyl anions generated from polyfluorocarboxamides

Heterocycles

Volumn 8, Issue 2, 2014, Pages 1201-1212

  Wakita, Natshumi ^a   Hara, Shoji ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84986586454     PISSN: 03855414     EISSN: 18810942     Source Type: Journal    
DOI: 10.3987/COM-13-S(S)84     Document Type: Article

References (43)

1. (a) D. J. Burton and Z.-Y. Yang, Tetrahedron, 1992, 48, 189
2. (b) M. A. McClinton and D. A. McClinton, Tetrahedron, 1992, 48, 6555
3. (c) G. K. S. Prakash and A. K. Yudin, Chem. Rev., 1997, 97, 757
4. (d) R. P. Singh and J. M. Shreeve, Tetrahedron, 2000, 56, 7613
5. (e) G. K. S. Prakash and M. Mandal, J. Fluorine Chem., 2001, 112, 123
6. (f) B. R. Langlois and T. Billard, Synthesis, 2003, 185
7. (g) J.-A. Ma and D. Cahard, Chem. Rev., 2004, 104, 6119
8. (h) T. Umemoto, 'Fluorine-Containing Synthons: Recent Advances in Perfluoroalkylation Methodology,' ed. by V. A. Soloshonok, American Chemical Society, Washington, DC, 2005, pp. 2-15
9. (i) G. K. S. Prakash and J. Hu, 'Fluorine-Containing Synthons: New Nucleophilic Fluoroalkylation Chemistry,' ed. by V. A. Soloshonok, American Chemical Society, Washington, DC, 2005, pp. 16-56
10. (j) B. R. Langlois and T. Billard, 'Fluorine-Containing Synthons: Fluoroform, Fluoral, Trifluoroacetic and Trifluoromethanesulfinic Acids Derivatives as New Reagents for the Introduction of Polyfluorinated Moieties,' ed. by V. A. Soloshonok, American Chemical Society, Washington, DC, 2005, pp. 57-86
11. (k) B. R. Langlois, T. Billard, and S. Roussel, J. Fluorine Chem., 2005, 126, 173
12. (l) G. K. S. Prakash and J. Hu, Acc. Chem. Res., 2007, 40, 921
13. (m) M. Médebielle and W. R. Dolbier Jr., J. Fluorine Chem., 2008, 129, 930
14. (n) J. Gawronski, N. Wascinska, and J. Gajewy, Chem. Rev., 2008, 108, 5227
15. (o) N. Shibata, S. Mizuta, and H. Kawai, Tetrahedron: Asymmetry, 2008, 19, 2633
16. (p) G. Valero, X. Companyó, and R. Rios, Chem. Eur. J., 2011, 17, 2018.
17. G. K. S. Prakash, R. Krishnamurti, and G. A. Olah, J. Am. Chem. Soc., 1989, 111, 393
18. R. Krishnamurti, D. R. Bellew, and G. K. S. Prakash, J. Org. Chem., 1991, 56, 984
19. R. P. Singh, G. Gao, R. L. Kirchmeier, and J. M. Shreeve, J. Org. Chem., 1999, 64, 2873
20. J. Kim and J. M. Shreeve, Org. Biomol. Chem., 2004, 2, 2728
21. J. J. Song, Z. Tan, J. T. Reeves, F. Gallou, N. K. Yee, and C. H. Senanayake, Org. Lett., 2005, 7, 2193
22. S. Mizuta, N. Shibata, S. Ogawa, H. Fujimoto, S. Nakamura, and T. Toru, Chem. Commun., 2006, 2575
23. V. V. Levin, A. D. Dilman, P. A. Belyakov, M. I. Struchkova, and V. A. Tartakovsky, Tetrahedron Lett., 2011, 52, 281.
24. (a) B. Folléas, I. Marek, J.-F. Normant, and L. S. Jalmes, Tetrahedron Lett., 1998, 39, 2973
25. (b) J. Russell and N. Roques, Tetrahedron, 1998, 54, 13771
26. (c) B. Folléas, I. Marek, J.-F. Normmant, and L. S. Jalmes, Tetrahedron, 2000, 56, 275
27. (d) S. Large, N. Roques, and B. R. Langlois, J. Org. Chem., 2000, 65, 8848
28. (e) T. Billard, S. Bruns, and B. R. Langlois, Org. Lett., 2000, 2, 2101.
29. C. Mispelaere and N. Roques, Tetrahedron Lett., 1999, 40, 6411
30. T. Billard, B. R. Langlois, and G. Blond, Eur. J. Org. Chem., 2001, 1467.
31. H. Kawai, Z. Yuan, E. Tokunaga, and N. Shibata, Org. Biomol. Chem., 2013, 11, 1446.
32. L. Jablonski, J. Joubert, T. Billard, and B. R. Langlois, Synlett, 2003, 230.
33. R. E. Sammelson and J. E. Casida, J. Org. Chem., 2003, 68, 8075.
34. T. Hudlicky, R. Fan, J. W. Reed, D. R. Carver, M. Hudlicky, and E. I. Eger II, J. Fluorine Chem., 1992, 59, 9.
35. J. Afzal, B. M. Fung, and E. A. O'rear, J. Fluorine Chem., 1987, 34, 385.
36. S. Ayuba, N. Yoneda, T. Fukuhara, and S. Hara, Bull. Chem. Soc. Jpn., 2002, 75, 1597.
37. T. Fukuhara and S. Hara, J. Org. Chem., 2010, 75, 7393.
38. H. C. Brown, J. S. Cha, B. Nazer, S.-C. Kim, S. Krishnamurthy, and C. A. Brown, J. Org. Chem., 1984, 49, 885.
39. H. A. Schenck, P. W. Lenkowski, I. C. Mukherjee, S.-H. Ko, J. P. Stables, M. K. Patel, and M. L. Brown, Bioorg. Med. Chem., 2004, 12, 979.
40. M. Shi, X.-G. Liu, Y.-W. Guo, and W. Zhang, Tetrahedron, 2007, 63, 12731.
41. M. G. Gorbunova, I. I. Gerus, and V. P. Kukhar, J. Fluorine Chem., 1993, 65, 25.
42. J. R. White, G. J. Price, P. K. Plucinski, and C. G. Frost, Tetrahedron Lett., 2009, 50, 7365.
43. C. Pooput, W. R. Dolbier, Jr., and M. Médebielle, J. Org. Chem., 2006, 71, 3564.