Synthesis of fluorinated β-ketosulfones and gem-disulfones by nucleophilic fluoroalkylation of esters and sulfinates with di- and monofluoromethyl sulfones

Journal of Organic Chemistry

Volumn 74, Issue 10, 2009, Pages 3767-3771

  Ni, Chuanfa ^a   Zhang, Laijun ^a   Hu, Jinbo ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL EQUATIONS; FUNCTIONALIZED; SULFINATES;

ESTERIFICATION; METHANE;

ESTERS;

ESTER; METHANE; SULFONE DERIVATIVE;

ALKYLATION; ARTICLE; FLUORINATION; METHYLATION; REACTION ANALYSIS; SYNTHESIS;

EID: 65949114058     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo900320b     Document Type: Article

References (54)

1. (a) Uneyama, K. Organofluorine Chemistry; Blackwell: Oxford, U.K., 2006.
2. (b) Kirsch, P. Modern Fluoroorganic Chemistry: Synthesis, Reactivity, Applications; Wiley-VCH: Weinheim, 2004.
3. (c) Chambers, R. D. Fluorine in Organic Chemistry; Blackwell: Oxford, U.K., 2004.
4. (d) Organofluorine Compounds: Chemistry and Applications; Hiyama, T., Ed.; Springer: New York, 2000.
5. (a) Prakash, G. K. S.; Hu, J. New Nucleophilic Fluoroalkylation Chemistry. In Fluorine-Containing Synthons; Soloshonok, V. A., Ed.; American Chemical Society: Washington, DC, 2005.
6. (b) Prakash, G. K. S.; Hu, J. Trihalomethyl Compounds. In Science of Synthesis; Charette, A. B., Ed.; Thieme: New York, 2005; Vol.22.
7. (c) Prakash, G. K. S.; Yudin, A. K. Chem. Rev. 1997, 97, 757-786.
8. (d) Prakash, G. K. S.; Mandal, M. J. Fluorine Chem. 2001, 112, 123-131.
9. Prakash, G. K. S.; Hu, J. Acc. Chem. Res. 2007, 40, 921-930.
10. Singh, R. P.; Shreeve, J. M. Tetrahedron 2000, 56, 7613-7632.
11. Langlois, B. R.; Billard, T. Synthesis 2003, 185-194.
12. (a) Wiedemann, J.; Heiner, T.; Mloston, G.; Prakash, G. K. S.; Olah, G. A. Angew. Chem., Int. Ed. 1998, 37, 820-821.
13. (b) Singh, R. P.; Cao, G.; Kirchmeier, R. L.; Shreeve, J. M. J. Org. Chem. 1999, 64, 2873-2876.
14. (c) Yokoyama, Y.; Mochida, K. Synlett 1997, 907-908.
15. Perfluoroalkylation of esters with lithium reagents: (d) Gassman, P. G.; O'Reilly, N. J. J. Org. Chem. 1987, 52, 2481-2490.
16. (e) Cregge, R. J.; Curran, T. T.; Metz, W. A. J. Fluorine Chem. 1998, 88, 71-77.
17. (f) Roques, N.; Russell, J. PCT Int. Appl. WO 9719038, 1997.
18. (g) Roques, N.; Russell, J. Tetrahedron 1998, 54, 13771-13782.
19. (a) Lequeux, T. P; Percy, J. M. J. Chem. Soc., Chem. Commun. 1995, 2111-2112.
20. (b) Blades, K.; Lequeux, T. P; Percy, J. M. Tetrahedron 1997, 53, 10623-10632.
21. (c) Berkowitz, D. B.; Eggen, M.; Shen, Q. R.; Shoemaker, R. K. J. Org. Chem. 1996, 61, 4666-4675.
22. (d) Phillion, D. P.; Cleary, D. G. J. Org. Chem. 1992, 57, 2763-2764.
23. (a) Kokotos, C. G.; Baskakis, C.; Kokotos, G. J. Org. Chem. 2008, 73, 8623-8626.
24. (b) Durham, S. L.; Hare, C. M.; Huber, E. W.; Janusz, M. J.; Koehl, J. R.; Marquart, A. L.; Mehdi, S.; Peet, N. P. J. Med. Chem. 1994, 37, 4538-4554.
25. (c) Johansson, A.; Poliakov, A.; Akerblom, E.; Wiklund, K.; Lindeberg, G.; Winiwarter, S.; Danielson, U. H.; Samuelsson, B.; Hallberg, A. Bioorg. Med. Chem. 2003, 11, 2551-2568.
26. (d) Perni, R. B.; Pitlik, J.; Britt, S. D.; Court, J. J.; Courtney, L. F.; Deininger, D. D.; Farmer, L. J.; Gates, C. A.; Harbeson, S. L.; Levin, R. B.; Lin, C.; Lin, K.; Moon, Y.-C.; Luong, Y.-P.; O'Malley, E. T.; Rao, B. G.; Thomson, J. A.; Tung, R. D.; Van Drie, J. H.; Wei, Y. Bioorg. Med. Chem. Lett. 2004, 14, 1441-1446.
27. (a) Lequeux, T. P.; Percy, J. M. J. Chem. Soc., Chem. Commun. 1995, 2111-2112.
28. (b) Blades, K.; Lequeux, T. P.; Percy, J. M. Tetrahedron 1997, 53, 10623-10632.
29. (a) Ni, C.; Li, Y.; Hu, J. J. Org. Chem. 2006, 71, 6829-6833.
30. (b) Fukuzumi, T.; Shibata, N.; Sugiura, M.; Yasui, H.; Nakamura, S.; Toru, T. Angew. Chem., Int. Ed. 2006, 45, 4973-4977.
31. (c) Prakash, G. K. S.; Chacko, S.; Alconcel, S.; Stewart, T.; Mathew, T.; Olah, G. A. Angew. Chem., Int. Ed. 2007, 46, 4933-4936.
32. (d) Mizuta, S.; Shibata, N.; Goto, Y.; Furukawa, T.; Nakamura, S.; Toru, T. J. Am. Chem. Soc. 2007, 129, 6394-6395.
33. (e) Prakash, G. K. S.; Zhao, X.; Chacko, S.; Wang, F.; Vaghoo, H.; Olah, G. A. Beilstein J. Org. Chem. 2008, 4, 17.
34. (f) Ni, C.; Zhang, L.; Hu, J. J. Org. Chem. 2008, 73, 5699-5713.
35. (g) Furukawa, T.; Shibata, N.; Mizuta, S.; Nakamura, S.; Toru, T.; Shiro, M. Angew. Chem., Int. Ed. 2008, 47, 8051-8054.
36. (a) Zajc, B.; Kake, S. Org. Lett. 2006, 8, 4457-4460.
37. (b) Alonso, D. A.; Fuensanta, M.; Gámez-Bengoa, E.; Nájera, C. Adv. Synth. Catal. 2008, 350, 1823-1829.
38. (c) Davis, F. A.; Han, W.; Murphy, C. K. J. Org. Chem. 1995, 60, 4730-4737.
39. (a) Pfund, E.; Lebargy, C.; Rouden, J.; Lequeux, T. J. Org. Chem. 2007, 72, 7871-7877.
40. (b) Nagura, H.; Fuchigami, T. Synlett 2008, 1714-1718.
41. (c) He, M.; Ghost, A. K.; Zajc, B. Synlett 2008, 999-1004.
42. (d) Motherwell, W. B.; Greaney, M. F.; Tocher, D. A. J. Chem. Soc., Perkin Trans. 1 2002, 2809-2815.
43. (e) Takeuchi, Y.; Asahina, K. H.; Koizumi, T. J. Chem. Soc., Perkin Trans. 1 1988, 1149-1153.
44. Stahly, G. P. J. Fluorine Chem. 1989, 43, 53-66.
45. Loghmani-Khouzani, H.; Poorheravi, M. R.; Sadeghi, M. M. M.; Caggiano, L.; Jackson, R. F. W. Tetrahedron 2008, 64, 7419-7425.
46. Prakash, G. K. S.; Hu, J.; Wang, Y.; Olah, G. A. Eur. J. Org. Chem. 2005, 2218-2223.
47. (a) Shimizu, M.; Fujimoto, T.; Minezaki, H.; Hata, T.; Hiyama, T. J. Am. Chem. Soc. 2001, 123, 6947-6948.
48. (b) Liu, X.; Shimizu, M.; Hiyama, T. Angew. Chem., Int. Ed. 2004, 43, 879-882.
49. Amii, H.; Kobaiyashi, T.; Hatamoto, Y.; Uneyama, K. Chem. Commun. 1999, 1323-1324, and the references cited therein.
50. Examples for the acylation of monofluorinated ester enolates: (a) Turner, J. A.; Jacks, W. S. J. Org. Chem. 1989, 54, 4229-4231.
51. (b) Bergmann, E. D.; Cohen, S. J. Chem. Soc. 1961, 4669-4671.
52. (c) Shahak, I.; Bergmann, E. D. J. Chem. Soc. 1960, 3225-3229.
53. (d) Bergmann, E. D.; Cohen, S.; Shahak, I. J. Chem. Soc. 1959, 3278-3285.
54. We noticed that there is only one example reported on the nucleophilic addition of chlorinated sulfone carbanion to the carbonyl group of dimethyl chloromaleate with low yield. See: Makosza, M.; Nizamov, S.; Kwast, A. Tetrahedron 2004, 60, 5413-5421.