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Abstract:

Perfluoroalkylation reactions of arenes have not been the subject of intense study as has been the case for the trifluoromethylation reactions of aromatics. However, the new synthetic methods proposed for achieving homolytic aromatic substitution reactions with perfluoroalkyl moieties have begun to claim a relevant role in functionalization reactions, as revealed by the interesting properties of arenes with large perfluoroalkyl chains. Methods for achieving Ar-Rf bonding reactions can be classified into thermal and photochemical, which can in turn make use of transition metals or be non-metal catalyzed. Reactions are mainly radical in nature. Radical methods for introducing Rf moieties into arenes have resulted as being the most popular and versatile options available to synthetic chemists. © The Royal Society of Chemistry 2015.

Registro:

Documento: Artículo
Título:Perfluoroalkylation reactions of (hetero)arenes
Autor:Barata-Vallejo, S.; 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, CIHIDECAR-CONICET, Ciudad Universitaria, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires Pabellón II, 3er Piso, Buenos Aires, 1428, Argentina
Palabras clave:Aromatic compounds; Substitution reactions; Transition metals; Bonding reactions; Functionalization reactions; Homolytic aromatic substitutions; Perfluoroalkyl chains; Perfluoroalkylation; Synthetic chemists; Synthetic methods; Trifluoromethylation; Photochemical reactions
Año:2015
Volumen:5
Número:77
Página de inicio:62498
Página de fin:62518
DOI: http://dx.doi.org/10.1039/c5ra11337g
Título revista:RSC Advances
Título revista abreviado:RSC Adv.
ISSN:20462069
CODEN:RSCAC
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_20462069_v5_n77_p62498_BarataVallejo

Referencias:

  • Wang, J., Sanchez-Rose, M., Aceña, J.L., Del Pozo, C., Sorochinsky, A.E., Fustero, S., Soloshonok, V.A., Liu, H., (2014) Chem. Rev., 114, p. 2432
  • Khlebnikova, T.S., Piven, Y.A., Beranovskii, A.V., Lakhvich, F.A., (2015) Russ. J. Org. Chem., 51 (5), p. 650
  • Ma, J.-A., Cahard, D., (2004) Chem. Rev., 104, p. 6119
  • Vaillard, S.E., Studer, A., Encyclopedia of Radicals in Chemistry, Biology and Materials (2012) Radical Arylations, 2, pp. 1059-1093. , in, ed. C. Chatgilialoglu and A. Studer, Wiley
  • Barata-Vallejo, S., Postigo, A., (2013) Coord. Chem. Rev., 257, p. 3051
  • Zhang, B., Studer, A., (2014) Org. Biomol. Chem., 12, p. 9895
  • Lantaño, B., Torviso, M.R., Bonesi, S.M., Barata-Vallejo, S., Postigo, A., (2015) Coord. Chem. Rev., 285, p. 76
  • Tomashenko, O.A., Grushin, V.V., (2011) Chem. Rev., 111, p. 4475
  • Ye, Y., Sanford, M.S., (2012) Synlett, p. 2005
  • Liu, T., Shen, Q., (2012) Eur. J. Org. Chem., p. 6679
  • Furuya, T., Kamlet, A.S., Ritter, T., (2011) Nature, 473, p. 470
  • Liang, T., Neumann, C.N., Ritter, T., (2013) Angew. Chem., Int. Ed, 52, p. 8214
  • O'Hara, F., Baxter, R.D., O'Brien, A.G., Collins, M.R., Dixon, J.A., Fujiwara, T., Ishihara, Y., Baran, P.S., (2013) Nat. Protoc., 8, p. 1042
  • Hfaiedh, A., Yuan, K., Ammar, H.B., Hassine, B.B., Soulé, J.-F., Doucet, H., (2015) ChemSusChem, 8, p. 1794
  • He, L., Natte, K., Rabeah, J., Taeschler, C., Neumann, H., Bruckner, A., Beller, M., (2015) Angew. Chem., Int. Ed, 54, p. 4320
  • Sladojevich, F., McNeill, E., Borgel, J., Zheng, S.-L., Ritter, T., (2015) Angew. Chem., Int. Ed, 54, p. 1
  • Charpentier, J., Früh, N., Togni, A., (2015) Chem. Rev., 115, p. 650
  • Pegot, B., Macé, Y., Urban, C., Diter, P., Blazejewski, J.-C., Magnier, E., (2012) J. Fluorine Chem., 134, p. 156
  • Alonso, C., Martínez De Marigorta, E., Rubiales, G., Palacios, F., (2015) Chem. Rev., 115, p. 1847
  • Takagi, T., Kanamori, T., (2011) J. Fluorine Chem., p. 427
  • O'Hara, F., Blackmond, D.G., Baran, P.S., (2013) J. Am. Chem. Soc., 135 (32), p. 12122
  • Fujiwara, Y., Dixon, J.A., O'Hara, F., Funder, E.D., Dixon, D.D., Rodriguez, R.A., Baxter, R.D., Baran, P.S., (2012) Nature, 492, p. 95
  • Kato, H., Hirano, K., Kurauchi, D., Toriumi, N., Uchiyama, M., (2015) Chem.-Eur. J., 21, p. 3895
  • Zhong, S., Hafner, A., Hussal, C., Nieger, M., Bräse, S., (2015) RSC Adv., 5, p. 6255
  • Matsugi, M., Hasegawa, M., Hasebe, S., Takai, S., Suyama, R., Wakita, Y., Kudo, K., Haga, S., (2008) Tetrahedron Lett., 49, p. 4189
  • Studer, A., Curran, D., (2014) Nat. Chem., 6, p. 765
  • Barata-Vallejo, S., Martin Flesia, M., Lantaño, B., Arguello, J.E., Peñéñory, A.B., Postigo, A., (2012) Eur. J. Org. Chem., p. 1889
  • Lantaño, B., Barata-Vallejo, S., Torviso, M.R., García, S.M., Tinnirello, A., Postigo, Al., (2014) Biointerface Res. Appl. Chem., 4, p. 853
  • Sladojevich, F., McNeill, E., Börgel, J., Zheng, S.-L., Ritter, T., (2015) Angew. Chem., Int. Ed, 54, p. 3712
  • Maroz, A., Hermann, R., Naumov, S., Brede, O., (2005) J. Phys. Chem. A, 109, p. 4690
  • Nagib, D.A., McMillan, D.W.C., (2011) Nature, 480, p. 224
  • Straathof, N.W., Van Osch, D.J.G.P., Schouten, A., Wang, X., Schouten, J.C., Hessel, V., Noeel, T., (2014) J. Flow Chem., 4, p. 12
  • Straathof, N.J.W., Gemoets, H.P.L., Wang, X., Schouten, J.C., Hessel, V., Noeel, T., (2014) ChemSusChem, 7, p. 1612
  • Nagib, D.A., Scott, M.E., MacMillan, D.W.C., (2009) J. Am. Chem. Soc., 131, p. 10875
  • Murphy, P.M., Baldwin, C.S., Buck, R.C., (2012) J. Fluorine Chem., 138, p. 3
  • Tiers, G.V.D., (1960) J. Am. Chem. Soc., 82, p. 5513
  • Matsugi, M., Hasegawa, M., Hasebe, S., Takai, S., Suyama, R., Wakita, Y., Kudo, K., Haga, S., (2008) Tetrahedron Lett., 49, p. 4189
  • Zhong, S., Hafner, A., Hussal, C., Nieger, M., Bräse, S., (2015) RSC Adv., 5, p. 6255
  • Brace, N.O., (1999) J. Fluorine Chem., 93, p. 1
  • Tejero, I., Huertas, I., Gonzalez-Lafont, A., Lluch, J.M., Marquet, J., (2005) J. Org. Chem., 70, p. 1718
  • Postigo, A., (2012) Can. J. Chem., 90 (6), pp. 493-497
  • Bravo, A., Bjørsvik, H.R., Fontana, F., Liguori, L., Mele, A., Minisci, F., (1997) J. Org. Chem., 62, p. 7128
  • Zhang, C.-P., Chen, Q.-Y., Guo, Y., Xiao, J.-C., Gu, Y.-C., (2012) Chem. Soc. Rev., 41, p. 4536
  • Long, Z.-Y., Chen, Q.-Y., (2000) Acta Chim. Sin., 58, p. 713
  • Huang, X.-T., Long, Z.-Y., Chen, Q.-Y., (2001) J. Fluorine Chem., 111, p. 107
  • Qi, Q., Shen, Q., Lu, L., (2011) Chin. J. Chem., 29, p. 2681
  • Qi, Q., Shen, Q., Lu, L., (2012) J. Fluorine Chem., 133, p. 115
  • Tordeux, M., Langlois, B., Wakselman, C., (1990) J. Chem. Soc., Perkin Trans. 1, p. 2293
  • Zhang Ch.-, P., Chen, Q.-Y., Guo, Y., Xiao, J.-Ch., Gub, Y.-Ch., (2012) Chem. Soc. Rev., 41, p. 4536
  • Jin, L.-M., Zeng, Z., Guo, C.-C., Chen, Q.-Y., (2003) J. Org. Chem., 68, p. 3912
  • Zeng, Z., Liu, C., Jin, L.-M., Guo, C.-C., Chen, Q.-Y., (2005) Eur. J. Org. Chem., p. 306
  • Jin, L.-M., Chen, L., Yin, J.-J., Guo, C.-C., Chen, Q.-Y., (2005) J. Fluorine Chem., 126, p. 1321
  • Cao, H.P., Xiao, J.C., Chen, Q.Y., (2006) J. Fluorine Chem., 127, p. 1079
  • Tanabe, Y., Matsuo, N., Ohno, N., (1988) J. Org. Chem., 53, p. 4582
  • Medebielle, M., Oturan, M.A., Pinson, J., Saveant, J.M., (1996) J. Org. Chem., 61, p. 1331
  • Lee, H., Czarnay, A., Batiste, M.A., Strekowski, L., (1998) J. Fluorine Chem., 91, p. 221
  • Lantaño, B., Barata-Vallejo, S., Postigo, A., (2014) Chem.-Eur. J., 20 (51), p. 10806
  • Morimoto, H., Tsubogo, T., Litvinas, N.D., Hartwig, J.F., (2011) Angew. Chem., Int. Ed., 50, p. 3793
  • Litvinas, N.D., Fier, P.S., Hartwig, J.F., (2012) Angew. Chem., Int. Ed., 51, p. 536
  • Lishchynskyi, A., Grushin, V.V., (2013) J. Am. Chem. Soc., 135, p. 12584
  • Hafner, A., Bihlmeier, A., Nieger, M., Klopper, W., Bräse, S., (2013) J. Org. Chem., 78, p. 7938
  • Huang, X.-T., Chen, Q.-Y., (2001) J. Org. Chem., 66, p. 4651
  • Loy, R.N., Sanford, M.S., (2011) Org. Lett., 13, pp. 2548-2551
  • Campeau, L.-C., Parisien, J.A.M., Fagnou, K., (2006) J. Am. Chem. Soc., 128, p. 581
  • Fuchikami, T., Ojima, I., (1983) J. Fluorine Chem., 22, p. 541
  • Lafrance, M., Fagnou, K., (2006) J. Am. Chem. Soc., 128, p. 16496
  • Li, Y., Li, Ch., Yue, W., Jiang, W., Kopecek, R., Qu, J., Wang, Z., (2010) Org. Lett., 12, p. 2374
  • Huang, W.Y., Xie, Y., (1990) Chin. J. Chem., 6, p. 536
  • He, L., Natte, K., Rabeah, J., Taeschler, Ch., Neumann, H., Brîckner, A., Beller, M., (2015) Angew. Chem., 127, p. 4394
  • Khrizanforov, M., Gryaznova, T., Sinyashin, O., Budnikova, Y., (2012) J. Organomet. Chem., 718, p. 101
  • Juang, K., Soulé, J.F., Doucet, H., (2015) Catalysis, 5, pp. 978-991
  • Tahara, R., Fukuhara, T., Hara, S., (2011) J. Fluorine Chem., 132, p. 579
  • Hafner, A., Feuerstein, T.J., Bräse, S., (2013) Org. Lett., 15, p. 3468
  • Kamigata, N., Yoshikawa, M., Shimizu, T.J., (1998) J. Fluorine Chem., 87, p. 91
  • Nakamura, T., Koga, Y., (1998) J. Chem. Soc., Perkin Trans. 2, pp. 659-662
  • Nappi, M., Bergonzini, G., Melchiorre, P., (2014) Angew. Chem., Int. Ed, 53, p. 4921
  • Cui, L., Matusaki, Y., Tada, N., Miura, T., Uno, B., Itoh, A., (2013) Adv. Synth. Catal., 355, p. 2203
  • Barata-Vallejo, S., Martin Flesia, M., Lantaño, B., Arguello, J.E., Peñéñory, A.B., Postigo, A., (2013) Eur. J. Org. Chem., 2013, p. 998
  • Lantaño, B., Barata-Vallejo, S., Torviso, M.R., Bonesi, S.M., Postigo, A., (2014) J. Fluorine Chem., 161, p. 134
  • Iizuka, M., Yoshida, M., (2009) J. Fluorine Chem., 130, p. 926
  • Ohkoshi, M., Yoshida, M., Matsuyama, H., Iyoda, M., (2001) Tetrahedron Lett., 42 (1), p. 33
  • Kamigata, N., Fukushima, T., Yoshida, M., (1990) Chem. Lett., 19, p. 649
  • Nagib, D.A., MacMillan, D.W.C., (2011) Nature, 480, p. 224
  • Pham, P.V., Nagib, D.A., MacMillan, D.W.C., (2011) Angew. Chem., Int. Ed., 50, p. 6119
  • Pham, P.V., Nagib, D.A., MacMillan, D.W.C., (2011) Angew. Chem., 123, p. 6243
  • Iqbal, N., Choi, S., Ko, E., Cho, E.J., (2012) Tetrahedron Lett., 53, p. 2005
  • Wang, L., Wei, X.-J., Lei, W.-L., Chen, H., Wu, L.-Z., Liu, Q., (2014) Chem. Commun., 50, p. 15916
  • Hessel, V., Kralisch, D., Kockmann, N., No, T., Wang, Q., (2013) ChemSusChem, 6, p. 746
  • Wegner, J., Ceylan, S., Kirschning, A., (2012) Adv. Synth. Catal., 354, p. 17
  • Glasnov, T.N., Kappe, C.O., (2011) Chem.-Eur. J., 17, p. 11956
  • Hartman, R.L., McMullen, J.P., Jensen, K.F., (2011) Angew. Chem., Int. Ed., 50, p. 7502
  • Hartman, R.L., McMullen, J.P., Jensen, K.F., (2011) Angew. Chem., 123, p. 7642
  • No, T., Buchwald, S.L., (2011) Chem. Soc. Rev., 40, p. 5010
  • No-l, T., Wang, X., Hessel, V., (2013) Chim. Oggi, 31, p. 10
  • Wang, X., Cuny, G.D., Noël, T., (2013) Angew. Chem., Int. Ed., 52, p. 7860
  • Wang, X., Cuny, G.D., Noël, T., (2013) Angew. Chem., 125, p. 8014
  • Nguyen, J.D., Reiß, B., Dai, C., Stephenson, C.R.J., (2013) Chem. Commun., 49, p. 4352
  • Rueping, M., Vila, C., Bootwicha, T., (2013) ACS Catal., 3, p. 1676
  • Neumann, M., Zeitler, K., (2012) Org. Lett., 14, p. 2658
  • Tucker, J.W., Zhang, Y., Jamison, T.F., Stephenson, C.R.J., (2012) Angew. Chem., Int. Ed., 51, p. 4144
  • Tucker, J.W., Zhang, Y., Jamison, T.F., Stephenson, C.R.J., (2012) Angew. Chem., 124, p. 4220
  • Straathof, N.J.W., Gemoets, H.P.L., Wang, X., Schouten, J.C., Hessel, V., Noeel, T., (2014) ChemSusChem, 7, p. 1612
  • Liu, X., Xu, C., Wang, M., Liu, Q., (2015) Chem. Rev., 115, p. 683

Citas:

---------- APA ----------
Barata-Vallejo, S., Bonesi, S.M. & Postigo, A. (2015) . Perfluoroalkylation reactions of (hetero)arenes. RSC Advances, 5(77), 62498-62518.
http://dx.doi.org/10.1039/c5ra11337g
---------- CHICAGO ----------
Barata-Vallejo, S., Bonesi, S.M., Postigo, A. "Perfluoroalkylation reactions of (hetero)arenes" . RSC Advances 5, no. 77 (2015) : 62498-62518.
http://dx.doi.org/10.1039/c5ra11337g
---------- MLA ----------
Barata-Vallejo, S., Bonesi, S.M., Postigo, A. "Perfluoroalkylation reactions of (hetero)arenes" . RSC Advances, vol. 5, no. 77, 2015, pp. 62498-62518.
http://dx.doi.org/10.1039/c5ra11337g
---------- VANCOUVER ----------
Barata-Vallejo, S., Bonesi, S.M., Postigo, A. Perfluoroalkylation reactions of (hetero)arenes. RSC Adv. 2015;5(77):62498-62518.
http://dx.doi.org/10.1039/c5ra11337g