Nucleophilic perfluoroalkylation of imines and carbonyls: Perfluoroalkyl sulfones as efficient perfluoroalkyl-transfer motifs

Organic Letters

Volumn 12, Issue 13, 2010, Pages 2932-2935

  Prakash, G K Surya ^a   Wang, Ying ^a   Mogi, Ryo ^a   Hu, Jinbo ^b   Mathew, Thomas ^a   Olah, George A ^a  

^a UNIVERSITY OF SOUTHERN CALIFORNIA   (United States)

^b SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; AMIDE; IMINE; KETONE; SULFONE;

ALKYLATION; ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

ALDEHYDES; ALKYLATION; AMIDES; IMINES; KETONES; MOLECULAR STRUCTURE; STEREOISOMERISM; SULFONES;

EID: 77954128587     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol100918d     Document Type: Article

References (47)

1. Hiyama, T., Eds. Organofluorine compounds. Chemistry and Applications, Springer: New York, 2000.
2. McCarthy, J. R. Utility of Fluorine in Biologically Active Molecules, ACS Fluorine Division Tutorial; 219th National ACS Meeting, San Francisco, March 26, 2000.
3. Banks, R. E.; Smart, B. E.; Tatlow, J. C. Organofluorine Chemistry: Principles and Commercial Applications; Plenum Press: New York, 1994.
4. McCarthy, J. R. Fluorine in Drug Design: A Tutorial Review; 17th Winter Fluorine Conference, St. Pete Beach, FL, 2005.
5. Bégué, J.-P.; Bonnet-Delpon, D. Bioorganic and Medicinal Chemistry of Fluorine; Wiley: Hoboken, NJ, 2007.
6. Motherwell, W. B.; Storey, L. J. J. Fluorine Chem. 2005, 126, 491
7. Prakash, G. K. S.; Mandal, M. J. Fluorine Chem. 2001, 112, 123
8. Russell, J.; Roques, N. Tetrahedron 1998, 54, 13771
9. Prakash, G. K. S.; Yudin, A. K. Chem. Rev. 1997, 97, 757
10. Krishnamurti, R.; Bellew, D. R.; Prakash, G. K. S. J. Org. Chem. 1991, 56, 984
11. Prakash, G. K. S.; Krishnamurti, R.; Olah, G. A. J. Am. Chem. Soc. 1989, 111, 393
12. Shreeve, J. M.; Yang, J.-J.; Kirchmeier, R. L. U. S. Patent 6215021, 2001.
13. Barhdadi, R.; Troupel, M.; Périchon, J. Chem. Commun. 1998, 1251
14. Umemoto, T. Chem. Rev. 1996, 96, 1757
15. Umemoto, T.; Ishihara, S. J. Am. Chem. Soc. 1993, 115, 2156
16. Umemoto, T.; Gotoh, Y. Bull. Chem. Soc. Jpn. 1987, 60, 3307
17. Dolbier, W. R., Jr. Top. Curr. Chem. 1997, 192, 97
18. Dolbier, W. R., Jr. Chem. Rev. 1996, 96, 1557
19. McClinton, M. A.; McClinton, D. A. Tetrahedron 1992, 48, 6555
20. Prakash, G. K. S.; Mandal, M.; Olah, G. A. Angew. Chem., Int. Ed. 2001, 40, 589
21. Prakash, G. K. S.; Mandal, M.; Olah, G. A. Org. Lett. 2001, 3, 2847
22. Prakash, G. K. S.; Mandal, M.; Olah, G. A. Synlett 2001, 1, 77
23. Cherneka, A. N.; Kolomeitsev, A. A.; Yagupolskij, Y. L.; Gentzsch, A.; Röshenthaler, G.-V. J. Fluorine Chem.. 1994, 70, 271
24. Sosnovskikh, V. Ya.; Sevenard, D. V.; Usachev, B. I.; Röshenthaler, G.-V. Tetrahedron Lett. 2003, 2097
25. Sonovskikh, V. Y.; Usachev, B. I.; Sevenard, D. V.; Röshenthaler, G.-V. J. Org. Chem. 2003, 68, 7747
26. Tverdomed, S. N.; Röshenthaler, G.-V.; Kalinovich, E. L.; Dogadina, A. V.; Ionin, B. I. J. Fluorine Chem. 2008, 129, 478
27. Pooput, C.; Dolbier, W. R., Jr.; Médebielle, M. J. Org. Chem. 2006, 71, 3564
28. Gassman, P. G.; OReilly, N. J. J. Org. Chem. 1987, 52, 2481
29. Gassman, P. G.; OReilly, N. J. Tetrahedron Lett. 1985, 26, 5243
30. Kitazume, T.; Ikeya, T. J. Org. Chem. 1988, 53, 2349
31. Kitazume, T.; Ishikawa, N. J. Am. Chem. Soc. 1985, 107, 5186
32. Prakash, G. K. S.; Hu, J.; Olah, G. A. Org. Lett. 2003, 5, 3253
33. Prakash, G. K. S.; Hu, J.; Mathew, T.; Olah, G. A. Angew. Chem., Int. Ed. 2003, 42, 5216
34. Prakash, G. K. S.; Hu, J. Acc. Chem. Res. 2007, 40, 921-930
35. Prakash, G. K. S.; Chacko, S. Curr. Opin. Drug Discovery Dev. 2008, 11, 793
36. Roques, N. J. Fluorine. Chem. 2001, 107, 311
37. Prakash, G. K. S.; Chacko, S.; Alconcel, S.; Stewart, T.; Mathew, T.; Olah, G. A. Angew. Chem. Int. Ed. 2007, 46, 4933
38. Prakash, G. K. S.; Xiaoming, Z.; Chacko, S.; Wang, F.; Vaghoo, H.; Olah, G. A. Beilstein J. Org. Chem. 2008, 4, 17
39. Prakash, G. K. S.; Wang, F.; Stewart, T.; Mathew, T.; Olah, G. A. Proc. Natl. Acad. Sci. U.S.A. 2009, 106, 4090
40. Moroni, M.; Koksch, B.; Osipov, S. N.; Crucianelli, M.; Frigerio, M.; Bravo, P.; Burger, K. J. Org. Chem. 2001, 66, 130
41. Burger, K.; Gaa, K.; Höss, E. J. Fluorine Chem. 1990, 47, 89
42. Berkowitz, D. B.; Karukurichi, K. R.; de la Salud-Bea, R.; Nelson, D. L.; McCune, C. D. J. Fluorine Chem. 2008, 129, 731
43. Allen, A. E.; MacMillan, D. W. C. J. Am. Chem. Soc. 2010, 132, 4986
44. Nagib, D. A.; Scott, M. E.; MacMillan, D. W. C. J. Am. Chem. Soc. 2009, 131, 10875
45. Kobayashi, Y.; Yamamoto, K.; Kumadaki, I. Tetrahedron Lett. 1979, 20, 4071
46. Carr, G. E.; Chambers, R. D.; Holmes, T. F. J. Chem. Soc., Perkin Trans. I 1988, 921
47. Chen, Q.; Duan, J. Tetrahedron Lett.. 1993, 34, 4241