Efficient and direct nucleophilic difluoromethylation of carbonyl compounds and imines with Me 3SiCF 2H at ambient or low temperature

Organic Letters

Volumn 13, Issue 19, 2011, Pages 5342-5345

  Zhao, Yanchuan ^a   Huang, Weizhou ^a   Zheng, Ji ^a   Hu, Jinbo ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

IMINE; KETONE; QUATERNARY AMMONIUM DERIVATIVE; TETRABUTYLAMMONIUM;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; HALOGENATION; METHYLATION; TEMPERATURE;

HALOGENATION; IMINES; KETONES; METHYLATION; MOLECULAR STRUCTURE; QUATERNARY AMMONIUM COMPOUNDS; TEMPERATURE;

EID: 80054718874     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol202208b     Document Type: Article

References (39)

1. Hiyama, T. Organofluorine Compounds: Chemistry and Applications; Springer: New York, 2000.
2. Banks, R. E.; Smart, B. E.; Tatlow, J. C. Organofluorine Chemistry: Principles and Commercial Applications; Plenum Press: New York, 1994.
3. Müller, K.; Faeh, C.; Diederich, F. Science 2007, 317, 1881.
4. Hagmann, W. K. J. Med. Chem. 2008, 51, 4359.
5. Kirk, K. L. Org. Process Res. Dev. 2008, 12. 305.
6. Ojima, I. Fluorine in Medicinal Chemistry and Chemical Biology;Wiley: Chichester, 2009.
7. Bégué, J. P.; Bonnet-Delpon, D. Bioorganic and Medicinal Chemistry of Fluorine; Wiley-VCH: Weinheim, 2008.
8. Uneyama, K. Organofluorine Chemistry; Blackwell: Oxford, 2006.
9. Uneyama, K. J. Fluorine Chem. 2008, 129, 550.
10. Erickson, J. A.; McLoughlin, J. I. J. Org. Chem. 1995, 60, 1626.
11. Sasson, R.; Hagooly, A.; Rozen, S. Org. Lett. 2003, 5, 769.
12. Li, Y.; Hu, J. Angew. Chem. 2005, 117, 6032.
13. Angew. Chem., Int. Ed. 2005, 44, 5882.
14. Prakash, G. K. S.; Weber, C.; Chacko, S.; Olah, G. A. Org. Lett. 2007, 9, 1863.
15. See a recent review on di- and monofluoromethylation reactions: Hu, J.; Zhang, W.; Wang, F. Chem. Commun. 2009, 7465.
16. Prakash, G. K. S.; Yudin, A. K. Chem. Rev. 1997, 97, 757.
17. Singh, R. P.; Shreeve, J. M. Tetrahedron 2000, 56, 7613.
18. Prakash, G. K. S.; Mandal, M. J. Fluorine. Chem. 2001, 112, 123.
19. Hartgraves, G. A.; Burton, D. J. J. Fluorine Chem. 1988, 39, 425.
20. Burton, D. J.; Hartgraves, G. A.; Hsu, J. Tetrahedron Lett. 1990, 31, 3699.
21. Burton, D. J.; Hartgraves, G. A. J. Fluorine Chem. 2007, 128, 1198.
22. Hagiwara, T.; Fuchikami, T. Synlett 1995, 717.
23. Prakash, G. K. S.; Hu, J. Acc. Chem. Res. 2007, 40, 921.
24. Yudin, A. K.; Prakash, G. K. S.; Deffieux, D.; Bradley, M.; Bau, R.; Olah, G. A. J. Am. Chem. Soc. 1997, 119, 1572.
25. Ni, C.; Hu, J. Tetrahedron Lett. 2005, 46, 8273.
26. Liu, J.; Ni, C.; Wang, F.; Hu, J. Tetrahedron. Lett. 2008, 49, 1605.
27. Zhu, L.; Li, Y.; Zhao, Y.; Hu, J. Tetrahedron Lett. 2010, 51, 6150.
28. Prakash,G.K. S.; Hu, J.; Wang, Y.; Olah, G. A. J. Fluorine Chem. 2005, 126, 527.
29. Pohmakotr, M.; Panichakul, D.; Tuchinda, P.; Reutrakul, V. Tetrahedron 2007, 63, 9429.
30. Li, Y.; Hu, J. J. Fluorine Chem. 2008, 129, 382.
31. Bootwicha, T.; Panichakul, D.; Kuhakarn, C.; Prabpai, S.; Kongsaeree, P.; Tuchinda, P.; Reutrakul, V.; Pohmakotr, M. J. Org. Chem. 2009, 74, 3798.
32. Qin, Y.-Y.; Qiu, X.-L.; Yang, Y.-Y.; Meng, W.-D.; Qing, F.-L. J. Org. Chem. 2005, 70, 9040.
33. Mizuta, S.; Shibata, N.; Ogawa, S.; Fujimoto, H.; Nakamura, S.; Toru, T. Chem. Commun. 2006, 2575.
34. Prakash, G. K. S.; Hu, J.; Olah, G. A. J. Org. Chem. 2003, 68, 4457.
35. Tyutyunov, A. A.; Boyko, V. E.; Igoumnov, S. M. Fluorine Notes, 2011, 74, 1; http://notes.fluorine1.ru/public/2011/1-2011/letters/ letter2.html.
36. Robak, M. T.; Herbage, M. A.; Ellman, J. A. Chem. Rev. 2010, 110, 3600.
37. Prakash, G. K. S.; Mandal, M.; Olah, G. A. Angew. Chem., Int. Ed. 2001, 40, 589.
38. Johnson, B. L.; Patel, M.; Rodgers, J. D.; Wang, H. S. WO 2001029037.
39. Mogi, R.; Morisaki, K.; Hu, J.; Prakash, G. K. S.; Olah, G. A. J. Fluorine Chem. 2007, 128, 1098.