Abstract:
Nucleophilic trifluoromethylation and perfluoroalkylation reactions have been the outstanding approach during the last few decades to effect fluoroalkyl group addition or substitution reactions. In most instances, perfluoroalkyl-metal species participate at the beginning of the reactions. In this account, however, the latest nucleophilic non-metal assisted or uncatalyzed trifluoromethylation and perfluoroalkylation reactions of substrates bearing biological relevance will be discussed. © 2014 Elsevier B.V.
Registro:
Documento: |
Artículo
|
Título: | Nucleophilic non-metal assisted trifluoromethylation and perfluoroalkylation reactions of organic substrates |
Autor: | Barata-Vallejo, S.; Torviso, M.R.; Lantaño, B.; Bonesi, S.M.; Postigo, A. |
Filiación: | Departamento de Química Orgánica, Facultad de Farmacia y Bioquímica, Universidad de Buenos Aires, Junín 954, Buenos Aires CP 1113, Argentina Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Buenos Aires CP 1428, Argentina
|
Palabras clave: | Fluorinated sulfides; Fluorinated sulfones; Fluorinated sulfoxides; Fluoroform; Nucleophilic trifluoromethylation; Trimethylsilyltrifluoromethane |
Año: | 2014
|
Volumen: | 161
|
Página de inicio: | 134
|
Página de fin: | 141
|
DOI: |
http://dx.doi.org/10.1016/j.jfluchem.2014.01.016 |
Título revista: | Journal of Fluorine Chemistry
|
Título revista abreviado: | J. Fluor. Chem.
|
ISSN: | 00221139
|
CODEN: | JFLCA
|
Registro: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00221139_v161_n_p134_BarataVallejo |
Referencias:
- Wu, X.-F., Neumann, H., Beller, M., (2012) Chem. Asian J., 7, pp. 1744-1754
- Tomashenko, O.A., Grushin, V.V., (2011) Chem. Rev., 111, pp. 4475-4521
- Langlois, B.R., Billard, T., Roussel, S., (2005) J. Fluorine Chem., 126, pp. 173-179
- Burton, D.J., Yang, Z.-Y., (1992) Tetrahedron, 48, pp. 189-275
- Shono, T., Ishifune, M., Okada, T., Kashimura, S., (1991) J. Org. Chem., 56, pp. 2-4
- Langlois, B.R., Billard, T., (2003) Synthesis, pp. 185-194
- Novak, P., Lishchynskyi, A., Grushin, V.V., (2012) J. Am. Chem. Soc., 134, pp. 16167-16170
- Prakash, G.K.S., Jog, P.V., Batamak, P.T.D., Olah, G.A., (2012) Science, 338, pp. 1324-1327
- Kawai, H., Yuan, Z.E., Tokunaga, E., Shibata, N., (2013) Org. Biomol. Chem., 11, pp. 1446-1450
- Folléas, B., Marek, I., Normant, J.-F., Saint-Jalmes, L., (2000) Tetrahedron, 56, pp. 275-283
- Luo, G.Y., Qu, J., (2013) New J. Chem., 37, pp. 3274-3280
- Zanardi, A., Novikov, M.A., Martin, E., Benet-Buchholz, J., Grushin, V.V., (2011) J. Am. Chem. Soc., 133, pp. 20901-20913
- Thomoson, C.S., Dolbier, Jr.W.R., (2013) J. Org. Chem., 78, pp. 8904-8908
- Zhang, Y., Fujiu, M., Serizawa, H., Mikami, K., (2013) J. Fluorine Chem., 156, pp. 367-371
- Prakash, G.K.S., Yudin, A.K., (1997) Chem. Rev., 97, pp. 757-786
- Boechat, N., Bastos, M.M., (2010) Curr. Org. Chem., 7, pp. 403-413
- Billard, T., Bruns, S., Langlois, B.R., (2000) Org. Lett., 2, pp. 2101-2103
- Large, S., Roques, N., Langlois, B.R., (2000) J. Org. Chem., 65, pp. 8846-8856
- Rubiales, G., Alonso, C., De, M.E., Marigorta, Palacios, F., (2014) Arkivoc, pp. 362-405
- Singh, R.P., Shreeve, J.M., (2012) J. Fluorine Chem., 133, pp. 20-26
- Langlois, B.R., Roques, N., (2007) J. Fluorine Chem., 128, pp. 1318-1325
- Mloston, G., Obijalska, E., Heimgartner, H., (2011) J. Fluorine Chem., 132, pp. 951-955
- Cheng, J.-L., Chu, L., Qing, F.-L., (2013) J. Fluorine Chem., 152, pp. 70-76
- Masusai, C., Soorukram, D., Kuhakarn, C., Tuchinda, P., Reutrakul, V., Pohmakotr, M., (2013) J. Fluorine Chem., 154, pp. 37-42
- Timoshenko, V.M., Portella, C., (2009) J. Fluorine Chem., 130, pp. 586-590
- Tlili, A., Billard, T., (2013) Angew. Chemie. Intern. Ed., 52, pp. 6818-6819
- Alazet, S., Ollivier, K., Billard, T., (2013) Beilstein J. Org. Chem., 9, pp. 2354-2357
- Kong, D., Jiang, Z., Xin, S., Bai, Z., Yuan, Y., Weng, Z., (2013) J. Fluorine Chem., 69, pp. 6046-6050
- Gouault-Bironneau, S., Timoshenko, V.M., Grellepois, F., Portella, C., (2012) J. Fluorine Chem., 134, pp. 164-171
- Dilman, A.D., Levin, V.V., (2011) Eur. J. Org. Chem., 2011, pp. 831-841
- Levin, V.V., Dilman, A.D., Belyakov, P.A., Struchkova, M.I., Tartakovsky, V.A., (2008) Eur. J. Org. Chem., 2008, pp. 5226-5230
- Dilman, A.D., Levin, V.V., Belyakov, P.A., Struchkova, M.I., Tartakovsky, V.A., (2008) Tetrahedron Lett., 49, pp. 4352-4354
- Zemtsov, A.A., Levin, V.V., Dilman, A.D., Struchkova, M.I., Belyakov, P.A., Tartakovsky, V.A., (2009) Tetrahedron Lett., 50, pp. 2998-3000
- Prakash, G.K.S., Hu, J., (2007) Acc. Chem. Res., 40, pp. 921-930
- Sakavuyi, K., Petersen, K.S., (2013) Tetrahedron Lett., 54, pp. 6129-6132
- Cherkupally, P., Beier, P., (2010) Tetrahedron Lett., 51, pp. 252-255
- Surya, G.K., Zhang, Z., Wang, F., Muñoz, S., Olah, G.A., (2013) J. Org. Chem., 78, pp. 3300-3305
- Rioski, M.V., Hart, A.D., Colby, D.A., (2013) Org. Lett., 15, pp. 208-211
Citas:
---------- APA ----------
Barata-Vallejo, S., Torviso, M.R., Lantaño, B., Bonesi, S.M. & Postigo, A.
(2014)
. Nucleophilic non-metal assisted trifluoromethylation and perfluoroalkylation reactions of organic substrates. Journal of Fluorine Chemistry, 161, 134-141.
http://dx.doi.org/10.1016/j.jfluchem.2014.01.016---------- CHICAGO ----------
Barata-Vallejo, S., Torviso, M.R., Lantaño, B., Bonesi, S.M., Postigo, A.
"Nucleophilic non-metal assisted trifluoromethylation and perfluoroalkylation reactions of organic substrates"
. Journal of Fluorine Chemistry 161
(2014) : 134-141.
http://dx.doi.org/10.1016/j.jfluchem.2014.01.016---------- MLA ----------
Barata-Vallejo, S., Torviso, M.R., Lantaño, B., Bonesi, S.M., Postigo, A.
"Nucleophilic non-metal assisted trifluoromethylation and perfluoroalkylation reactions of organic substrates"
. Journal of Fluorine Chemistry, vol. 161, 2014, pp. 134-141.
http://dx.doi.org/10.1016/j.jfluchem.2014.01.016---------- VANCOUVER ----------
Barata-Vallejo, S., Torviso, M.R., Lantaño, B., Bonesi, S.M., Postigo, A. Nucleophilic non-metal assisted trifluoromethylation and perfluoroalkylation reactions of organic substrates. J. Fluor. Chem. 2014;161:134-141.
http://dx.doi.org/10.1016/j.jfluchem.2014.01.016