Nucleophilic difluoromethylation of C=N bonds in heterocycles with difluoromethyl silane reagents

Tetrahedron

Volumn 68, Issue 26, 2012, Pages 5137-5144

  Huang, Weizhou ^a   Ni, Chuanfa ^a   Zhao, Yanchuan ^a   Zhang, Wei ^a   Dilman, Alexander D ^b   Hu, Jinbo ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

^b N D ZELINSKY INSTITUTE OF ORGANIC CHEMISTRY   (Russian Federation)

Author keywords

Fluorine chemistry; Fluoroalkylation; Heterocycles; Nucleophilic reaction; Silane reagents

Indexed keywords

FLUOROMETHANE; HETEROCYCLIC COMPOUND; ISOQUINOLINE DERIVATIVE; PYRIDINE DERIVATIVE; QUINOLINE DERIVATIVE; REAGENT; SILANE DERIVATIVE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL BOND; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; PRIORITY JOURNAL;

EID: 84861695037     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2012.04.039     Document Type: Article

References (33)

1. I. Ojima Fluorine in Medicinal Chemistry and Chemical Biolog 2009 Wiley Chichester
2. J.-P. Bégué, and D. Bonnet-Delpon Bioorganic and Medicinal Chemistry of Fluorine 2008 Wiley-VCH Weinheim
3. R. Filler, and R. Saha Future Med. Chem. 1 2009 777
4. J. Liu, and J. Hu Future Med. Chem. 1 2009 875
5. A.E. Sorochinsky, and V.A. Soloshonok J. Fluorine Chem. 131 2010 127
6. G.K.S. Prakash, R. Mogi, and G.A. Olah Org. Lett. 8 2006 3589
7. A.D. Dilman, and V.V. Levin Eur. J. Org. Chem. 2011 831
8. R. Loska, and M. Makosza J. Org. Chem. 72 2007 1354
9. R. Loska, M. Majcher, and M. Makosza J. Org. Chem. 72 2007 5574
10. V.V. Levin, M.A. Kozlov, Y.-H. Song, A.D. Dilman, P.A. Belyakov, M.I. Struchkova, and V.A. Tartakovsky Tetrahedron Lett. 49 2008 3108
11. V.V. Levin, A.D. Dilman, P.A. Belyakov, M.I. Struchkova, and V.A. Tartakovsky Eur. J. Org. Chem. 2008 5226
12. N.E. Shevchenko, K. Vlasov, V.G. Nenajdenko, and G.-V. Röschenthaler Tetrahedron 67 2011 69
13. V.A. Petrov Fluorinated Hererocyclic Compounds: Synthesis, Chemistry, and Applications 2009 John Wiley Hobken
14. C.P. Felix, N. Khatimi, and A.J. Laurent Tetrahedron Lett. 35 1994 3303
15. R.E. Banks, M.K. Besheesh, N.J. Lawrence, and D.J. Tovell J. Fluorine Chem. 97 1999 79
16. V.A. Petrov Tetrahedron Lett. 41 2000 6959
17. Very recently, nucleophilic difluromethylation of acyclic imines with fluoroalkyl silanes activated by a Bronsted acid was reported by Dilman and co-workers. See M.D. Kosobokov, A.D. Dilman, M.I. Struchkova, P.A. Belyakov, and J. Hu J. Org. Chem. 77 2012 2080
18. J. Hu, W. Zhang, and F. Wang Chem. Commun. 2009 7467
19. F. Werner, N. Blank, and T. Opatz Eur. J. Org. Chem. 2007 3911
20. A.P. Venkov, and I.I. Ivanov Tetrahedron 52 1996 12299
21. N.M. Gray, B.K. Cheng, S.J. Mick, C.M. lair, and P.C. Contreras J. Med. Chem. 32 1989 1242
22. M.C. Elliott, and E. Williams Org. Biomol. Chem. 1 2003 3038
23. D.H. Hua, S.W. Miao, S.N. Bharathi, T. Katsuhira, and A.A. Bravo J. Org. Chem. 55 1990 3682
24. G.K.S. Prakash, and J. Hu Acc. Chem. Res. 40 2007 921
25. C. Ni, and J. Hu Synlett 2011 770
26. Y. Zhao, W. Huang, J. Zheng, and J. Hu Org. Lett. 13 2011 5342
27. Y. Li, and J. Hu Angew. Chem., Int. Ed. 44 2005 5882
28. Y. Li, and J. Hu Angew. Chem., Int. Ed. 46 2007 2489
29. G.K.S. Prakash, R. Krishnamuti, and G.A. Olah J. Am. Chem. Soc. 111 1989 393
30. G.K.S. Prakash, and M. Mandal J. Fluorine Chem. 112 2001 123
31. C. Ni, and J. Hu Tetrahedron Lett. 46 2005 8273
32. G.K.S. Prakash, J. Hu, Y. Wang, and G.A. Olah Eur. J. Org. Chem. 2005 2218
33. K. Fujikawa, Y. Fujioka, A. Kobayashi, and H. Amii Org. Lett. 13 2011 5560