Nucleophilic trifluoromethylation of arylidenemalononitriles

Tetrahedron Letters

Volumn 49, Issue 28, 2008, Pages 4352-4354

  Dilman, Alexander D ^a   Levin, Vitalij V ^a   Belyakov, Pavel A ^a   Struchkova, Marina I ^a   Tartakovsky, Vladimir A ^a  

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

Author keywords

Arylidenemalononitriles; Michael reaction; Trifluoromethylation

Indexed keywords

2 [3 PHENYL 1 (TRIFLUORONETHYL)PROP 2 ENYL]MALONONITRILE; IDENEMALONONITRILE DERIVATIVE; LEWIS BASE; N,N DIMETHYLFORMAMIDE; NITRILE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; FLUORINATION; METHYLATION; MICHAEL ADDITION; ROOM TEMPERATURE; SYNTHESIS;

EID: 44649136766     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.05.039     Document Type: Article

References (33)

1. 3, see:. Prakash G.K.S., and Yudin A.K. Chem. Rev. 97 (1997) 757
2. Prakash G.K.S., and Mandal M. J. Fluorine Chem. 112 (2001) 123
3. Singh R.P., and Shreeve J.M. Tetrahedron 56 (2000) 7613
4. Ma J.-A., and Cahard D. J. Fluorine Chem. 128 (2007) 975
5. For addition to C{double bond, long}O bonds, see:. Prakash G.K.S., Panja C., Vaghoo H., Surampudi V., Kultyshev R., Mandal M., Rasul G., Mathew T., and Olah G.A. J. Org. Chem. 71 (2006) 6806
6. Kawano Y., Kaneko N., and Mukaiyama T. Bull. Chem. Soc. Jpn. 79 (2006) 1133
7. Mizuta S., Shibata N., Akiti S., Fujimoto H., Nakamura S., and Toru T. Org. Lett. 9 (2007) 3707
8. Fustero S., Albert L., Acena J.L., Sanz-Cervera J.F., and Asensio A. Org. Lett. 10 (2008) 605
9. For addition to C{double bond, long}N bonds, see:. Prakash G.K.S., Mandal M., and Olah G.A. Synlett (2001) 77
10. Prakash G.K.S., Mogi R., and Olah G.A. Org. Lett. 8 (2006) 3589
11. Kirij N.V., Babadzhanova L.A., Movchun V.N., Yagupolskii Y.L., Tyrra W., Naumann D., Fischer H.T.M., and Scherer H. J. Fluorine Chem. 129 (2008) 14
12. Nelson D.W., Owens J., and Hiraldo D. J. Org. Chem. 66 (2001) 2572
13. Sosnovskikh V.Ya., Sevenard D.V., Usachev B.I., and Röschenthaler G.-V. Tetrahedron Lett. 44 (2003) 2097
14. Sosnovskikh V.Ya., Usachev B.I., Sevenard D.V., and Röschenthaler G.-V. J. Org. Chem. 68 (2003) 7747
15. Sosnovskikh V.Ya., Usachev B.I., Sevenard D.V., and Röschenthaler G.-V. J. Fluorine Chem. 126 (2005) 779
16. Sosnovskikh V.Ya., Usachev B.I., Permyakov M.N., Sevenard D.V., and Röeschenthaler G.-V. Russ. Chem. Bull. 55 (2006) 1687
17. Sevenard D.V., Sosnovskikh V.Ya., Kolomeitsev A.A., Königsmann M.H., and Röschenthaler G.-V. Tetrahedron Lett. 44 (2003) 7623
18. 3, see:. Dilman A.D., Arkhipov D.E., Levin V.V., Belyakov P.A., Korlyukov A.A., Struchkova M.I., and Tartakovsky V.A. J. Org. Chem. 72 (2007) 8604
19. Levin V.V., Kozlov M.A., Song Y.-H., Dilman A.D., Belyakov P.A., Struchkova M.I., and Tartakovsky V.A. Tetrahedron Lett. 49 (2008) 3108
20. Dilman A.D., Gorokhov V.V., Belyakov P.A., Struchkova M.I., and Tartakovsky V.A. Russ. Chem. Bull. 56 (2007) 1522
21. 5-substituted silanes, see:. Dilman A.D., Belyakov P.A., Korlyukov A.A., Struchkova M.I., and Tartakovsky V.A. Org. Lett. 7 (2005) 2913
22. Dilman A.D., Levin V.V., Karni M., and Apeloig Y. J. Org. Chem. 71 (2006) 7214
23. Dilman A.D., Levin V.V., Belyakov P.A., Struchkova M.I., and Tartakovsky V.A. Synthesis (2006) 447
24. Levin V.V., Dilman A.D., Belyakov P.A., Korlyukov A.A., Struchkova M.I., Antipin M.Y., and Tartakovsky V.A. Synthesis (2006) 489
25. Levin V.V., Dilman A.D., Belyakov P.A., Korlyukov A.A., Struchkova M.I., and Tartakovsky V.A. Mendeleev Commun. (2007) 105
26. Dilman A.D., Gorokhov V.V., Belyakov P.A., Struchkova M.I., and Tartakovsky V.A. Tetrahedron Lett. 47 (2006) 6217
27. Levin V.V., Dilman A.D., Belyakov P.A., Struchkova M.I., and Tartakovsky V.A. Tetrahedron Lett. 47 (2006) 8959
28. Bordwell F.G. Acc. Chem. Res. 21 (1988) 456
29. For the electrophilicity parameters of arylidenemalononitriles, see:. Lemek T., and Mayr H. J. Org. Chem. 68 (2003) 6880
30. 5:. Bardin V.V., Pressman L.S., and Cherstkov V.F. Synth. Commun. 25 (1995) 2425
31. 5:. Eaborn C., Treverton J.A., and Walton D.R.M.. J. Organomet. Chem. 9 (1967) 259
32. 2F:. Joste R., and Ruppert I. J. Organomet. Chem. 329 (1987) 313
33. 3): 24.4 (q, J = 2.5)