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Abstract:

Metal-assisted trifluoromethylation and perfluoroalkylation reactions are probably one of the first approaches employed to achieve fluoroalkyl-group substitutions of organic substrates through the use of metals such as copper. Fluoroalkylation reactions of both aromatic and aliphatic substrates involving the employment of perfluoroalkyl halides RfX in conjunction with metallic species, and nucleophilic fluoroalkylating reagents in the presence of metals or organometallic species will be studied. Fluoroalkylation reactions utilizing electrophilic fluoroalkylating reagents in the presence of transition metals or trifluoromethylthiolation reactions will not be the subject of this article. Recently emerging literature (2011-present), with special emphasis on updates from previous review articles on the metal-mediated fluoroalkylation of aromatic substrates will be dealt with. © 2014 Elsevier B.V.

Registro:

Documento: Artículo
Título:Advances in metal-assisted non-electrophilic fluoroalkylation reactions of organic compounds
Autor:Lantaño, B.; Torviso, M.R.; Bonesi, S.M.; Barata-Vallejo, S.; 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 Ciencias Básicas, Universidad Nacional de Luján, Luján, Buenos Aires, Argentina
Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires. Ciudad Universitaria, Pab. II, 3er piso-CIHIDECAR-CONICET, Buenos Aires, CP 1428, Argentina
Palabras clave:Fluoroalkylation of aromatics; Metal-assisted trifluoromethylation; Trifluoromethylation by metal-organic species
Año:2015
Volumen:285
Página de inicio:76
Página de fin:108
DOI: http://dx.doi.org/10.1016/j.ccr.2014.11.004
Título revista:Coordination Chemistry Reviews
Título revista abreviado:Coord. Chem. Rev.
ISSN:00108545
CODEN:CCHRA
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00108545_v285_n_p76_Lantano

Referencias:

  • Tomashenko, O.A., Grushin, V.V., (2011) Chem. Rev., 111, p. 4475
  • Ye, Y., Sanford, M.S., (2012) Synlett, 23, p. 2005
  • Liu, T., Shen, Q., (2012) Eur. J. Org. Chem., 2012, 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
  • Barata-Vallejo, S., Postigo, A., (2013) Coord. Chem. Rev., 257, p. 3051
  • Chen, P., Liu, G., (2013) Synthesis, 45, p. 2919
  • Grushin, V.V., Marshall, J.W., (2006) J. Am. Chem. Soc., 128, p. 12644
  • Bravo, A., Borsvik, H.R., Fontana, F., Liguori, L., Minisci, F., (1997) J. Org. Chem., 62, p. 7128
  • Studer, A., (2012) Angew. Chem. Int. Ed., 51, p. 8950
  • Postigo, A., (2012) Can. J. Chem., 90, p. 493
  • O'Hara, F., Blackmond, D.G., Baran, P.S., (2013) J. Am. Chem. Soc., 135, p. 12122
  • Fujiwara, Y., Dixon, J.A., O'Hara, F., Funder, D.E., Dixon, D.D., Rodriguez, R.A., Baxter, R.D., Baran, P.S., (2012) Nature, 492, p. 95
  • Maleckis, A., Sanford, M.S., (2014) Organomet, 33, p. 3831
  • Lee, E., Hooker, J.M., Ritter, T., (2012) J. Am. Chem. Soc., 134, p. 17456
  • Barata-Vallejo, S., Lantaño, B., Postigo, A., (2014) Chem. Eur. J.
  • Ye, Y., Kunzi, S.A., Sanford, M.S., (2012) Org. Lett., 14, p. 4979
  • Charpentier, J., Früh, N., Togni, A., (2014) Chem. Rev.
  • Ullrich, J., (2012) Top. Curr. Chem., 320, p. 191
  • Jin, Z., Hammond, G.B., Xu, B., (2012) Aldrichimica Acta, 45, p. 66
  • Konovalov, A.I., Lishchynskyi, A., Grushin, V.V., (2014) J. Am. Chem. Soc., p. 64
  • Cho, E.J., Senecal, T.D., Kinzel, T., Zhang, Y., Watson, D.A., Buchwald, S.L., (2010) Science, 328, p. 1679
  • Ye, Y., Ball, N.D., Kampf, J.W., Sanford, M.S., (2010) J. Am. Chem. Soc., 132, p. 14682
  • Wang, X., Truesdale, L., Yu, J.-Q., (2010) J. Am. Chem. Soc., 132, p. 3648
  • Mu, X., Chen, S., Zhen, X., Liu, G., (2011) Chem. Eur. J., 17, p. 6039
  • Loy, R.N., Sanford, M.S., (2011) Org. Lett., 13, p. 2548
  • Barata-Vallejo, S., Rosario Torviso, M., Lantaño, B., Bonesi, S.M., Postigo, A., (2014) J. Fluorine Chem., 161, p. 134
  • Xu, L., Jiang, H., Hao, J., Zhao, G., (2014) Tetrahedron, 70, p. 4373
  • Gonda, Z., Kovács, S., Wáber, C., Gáti, T., Mászáros, A., Kotschy, A., Novák, Z., (2014) Org. Lett., 16, p. 4268
  • Cerettaa, F., Zaggiaa, A., Contea, L., Ameduri, B., (2012) J. Fluorine Chem., 135, p. 220
  • Mazloomi, Z., Bansode, A., Benavente, P., Lishchynskyi, A., Urakawa, A., Grushin, V.V., (2014) Org. Process Res. Dev.
  • Lishchynskyi, A., Novikov, M.A., Martin, E., Escudero-Adán, E.C., Novák, P., Grushin, V.V., (2013) J. Org. Chem., 78, p. 11126
  • Clark, J.H., Denness, J.E., McClinton, M.A., Wynd, A.J., (1990) J. Fluorine Chem., 50, p. 411
  • Wu, X.-F., Neumann, H., Beller, M., (2012) Chem. Asian J., 7, p. 1744
  • Konovalov, A.I., Benet-Buchholz, J., Martin, E., Grushin, V.V., (2013) Angew. Chem. Int. Ed., 52, p. 11637
  • Lishchynskyi, A., Grushin, V.V., (2013) J. Am. Chem. Soc., 135, p. 12584
  • Novák, P., Lishchynskyi, A., Grushin, V.V., (2012) Angew. Chem. Int. Ed., 51, p. 7767
  • Serizawa, H., Aikawa, K., Mikami, K., (2013) Chem. Eur. J., 19, p. 17692
  • Chen, Q.-Y., Wu, S.-W., (1989) J. Chem. Soc. Perkin Trans. 1, p. 2385
  • Fier, P.S., Hartwig, J.F., (2012) J. Am. Chem. Soc., 134, p. 5524
  • Prakash, G.K.S., Hu, J., Olah, G.A., (2003) J. Org. Chem., 68, p. 4457
  • Gao, B., Ni, C., Hu, J., (2014) CHIMIA Int. J. Chem., 68, p. 414
  • Litvinas, N.D., Fier, P.S., Hartwig, J.F., (2012) Angew. Chem. Int. Ed., 51, p. 563
  • Mormino, M.G., Fier, P.S., Hartwig, J.F., (2014) Org. Lett., 16, p. 1744
  • Tomashenko, O.A., Escudero-Adán, E.C., Martínez Belmonte, M., Grushin, V.V., (2011) Angew. Chem. Int. Ed., 50, p. 7655
  • Knauber, T., Arikan, F., RÖshenthaler, G.-V., Gooßen, L.J., (2011) Chem. Eur. J., 17, p. 2689
  • Oishi, M., Kondo, H., Amii, H., (2009) Chem. Commun., p. 1909
  • Urata, H., Fuchikami, H., (1991) Tetrahedron Lett., 32, p. 91
  • Liu, X., Xu, C., Wang, M., Liu, Q., (2014) Chem. Rev., p. 73a
  • Serizawa, H., Aikawa, K., Mikami, K., (2014) Org. Lett., 16, p. 3456
  • Nishida, T., Ida, H., Kuninobu, Y., Kanai, M., (2014) Nat. Commun.
  • Milne, J.E., Buchwald, S.L., (2004) J. Am. Chem. Soc., 126, p. 13028
  • Surry, D.S., Buchwald, S.L., (2008) Angew. Chem. Int. Ed., 47, p. 6338
  • Barder, T.E., Buchwald, S.L., (2007) J. Am. Chem. Soc., 129, p. 12003
  • Biscoe, M.R., Fors, B.P., Buchwald, S.L., (2008) J. Am. Chem. Soc., 130, p. 6686
  • Maleckis, A., Sanford, M.S., (2014) Organomet, 33, p. 2653
  • Nagib, D.A., MacMillan, D.W.C., (2011) Nature, 480, p. 224
  • Liu, T., Shao, X., Wu, Y., Shen, Q., (2012) Angew. Chem. Int. Ed., 51, p. 540
  • Kirsch, P., (2004) Modern Fluororganic Chemistry. Synthesis, Reactivity and Applications, , Wiley-VCH-GmbH, Weinheim
  • Ye, Y., Sanford, M.S., (2012) J. Am. Chem. Soc., 134, p. 9034
  • Senecal, T.D., Parsons, A.T., Buchwald, S.L., (2011) J. Org. Chem., 76, p. 1174
  • Chu, L., Qing, F.-L., (2010) Org. Lett., 12, p. 5060
  • Zhu, R., Buchwald, S.L., (2012) J. Am. Chem. Soc., 134, p. 12462
  • Chu, L., Qing, F.-L., (2014) Acc. Chem. Res., 47, p. 1513
  • Dubbaka, S.R., Salla, M., Bolisetti, R., Nizalapur, S., (2014) RSC Adv., 4, p. 6496
  • Feng, Z., Min, Q.-Q., Xiao, Y.-L., Zhang, B., Zhang, X., (2014) Angew. Chem. Int. Ed., 53, p. 1669
  • Feng, Z., Chen, F., Zhang, X., (2012) Org. Lett., 14, p. 1938
  • Xiao, Y.-L., Zhang, B., Feng, Z., Zhang, X., (2014) Org. Lett., 16, p. 4822
  • Chen, Q.Y., Yang, Z.Y., (1985) Acta Chim. Sinica, 44, p. 1118
  • Yang, Z.-Y., Burton, D.J., (1992) J. Org. Chem., 57, p. 4676
  • Qi, Q., Shen, Q., Lu, L., (2012) J. Am. Chem. Soc., 134, p. 6548
  • Molander, G.A., Ito, T., (2001) Org. Lett., 3, p. 393
  • Molander, G.A., Biolatto, B.T., (2003) J. Org. Chem., 68, p. 4302
  • Molander, G.A., Figueroa, R., (2006) Org. Lett., 8, p. 75
  • Quach, T.D., Batey, R.A., (2003) Org. Lett., 5, p. 1381
  • Quach, T.D., Batey, R.A., (2003) Org. Lett., 5, p. 4397
  • Santos-Filho, E.F., Sousa, J.C., Bezerra, N.M.M., Menezes, P.H., Oliveira, R.A., (2011) Tetrahedron Lett., 52, p. 5288
  • Min, Q.-Q., Yin, Z., Feng, Z., Guo, W.-H., Zhang, X., (2014) J. Am. Chem. Soc., 136, p. 1230
  • Yu, Y.-B., He, G.-Z., Zhang, X., (2014) Angewandte Chemie, 126, p. 10625
  • Ma, G., Wan, W., Hu, Q., Jiang, H., Wang, J., Zhu, S., Hao, J., (2014) Chem. Commun., 50, p. 7527
  • Browne, D.L., (2014) Angew. Chem. Int. Ed., 53, p. 1482
  • Dai, J.-J., Fang, C., Xiao, B., Yi, J., Liu, Z.-J., Lu, X., Fu, Y., (2013) J. Am. Chem. Soc., 135, p. 8436
  • Wang, X., Xu, Y., Mo, F., Ji, G., Qiu, D., Feng, J., Ye, Y., Wang, J., (2013) J. Am. Chem. Soc., 135, p. 10330
  • Furuya, T., Strom, A.E., Ritter, T., (2009) J. Am. Chem. Soc., 131, p. 1662
  • Tang, P., Furuya, T., Ritter, T., (2010) J. Am. Chem. Soc., 132, p. 12150
  • Huang, C., Liang, T., Harada, S., Lee, E., Ritter, T., (2011) J. Am. Chem. Soc., 133, p. 13308
  • Danoun, G., Bayarmagnai, B., Grünberg, M.F., Gooßen, L.J., (2013) Angew. Chem. Int. Ed., 52, p. 7972
  • Bayarmagnai, B., Matheis, C., Risto, E., Gooßen, L.J., (2014) Adv. Synth. Catal., 356, p. 2343
  • Lishchynskyi, A., Berthon, G., Grushin, V., (2014) Chem. Commun., 50, p. 10237
  • Bayarmagnai, B., Matheis, C., Risto, E., Goossen, L.J., (2014) Adv. Synth. Cat., 356, p. 2343
  • Besset, T., Schneider, C., Cahard, D., (2012) Angew. Chem. Int. Ed., 51, p. 5048
  • Zhang, X.-G., Dai, H.-X., Wasa, M., Yu, J.-Q., (2012) J. Am. Chem. Soc., 134, p. 11948
  • Loy, R.N., Sanford, M.S., (2010) Org. Lett., 13, p. 2548
  • Iqbal, N., Choi, S., Ko, E., Cho, E.J., (2012) Tetrahedron Lett., 53, p. 2005
  • Zeng, U., Zhang, L., Zhao, Y., Ni, C., Zhao, J., Hu, J., (2013) J. Am. Chem. Soc., 135, p. 2955
  • He, R.-Y., Zeng, H.-T., Huang, J.-M., (2014) Eur. J. Org. Chem.
  • Yang, Y.-D., Iwamoto, K., Tokunaga, E., Shibata, N., (2013) Chem. Commun., 49, p. 5510
  • Seo, S., Taylor, J.B., Greany, M.F., (2013) Chem. Commun., 49, p. 6385
  • Chu, L., Qing, F.-L., (2012) J. Am. Chem. Soc., 134, p. 1298
  • Fennenwald, J.C., Lipshutz, B.H., (2014) Green Chem., 16, p. 1097
  • Gakh, A.A., Shermolovich, Y., (2014) Curr. Top. Med. Chem., 14, p. 952
  • Cao, X.-H., Pan, X., Zhou, P.-J., Zou, P.J., Asekun, O.T., (2014) Chem. Commun., 50, p. 3359
  • Kino, T., Nagase, Y., Ohtsuka, Y., Yamamoto, K., Uraguchi, D., Tokuhisa, K., Yamakawa, T., (2010) J. Fluorine Chem., 131, p. 98
  • Ohtsuka, Y., Yamakawa, T., (2011) Tetrahedron, 67, p. 2323
  • Sun, X., Yu, S., (2014) Org. Lett., 16, p. 2938
  • Hafner, A., Feuerstein, T.J., Bräse, S., (2013) Org. Lett., 15, p. 3468
  • Hafner, A., Bihlmeier, A., Nieger, M., Klopper, W., Bräse, S., (2013) J. Org. Chem., 78, p. 7938
  • Jiang, X., Qing, F.-L., (2013) Beilstein J. Org. Chem., 9, p. 2862
  • Landelle, G., Panossian, A., Pazenok, S., Vors, J.-P., Leroux, F.R., (2013) Beilstein J. Org. Chem., 9, p. 2476
  • Xu, J., Xiao, B., Xie, C.-Q., Luo, D.-F., Liu, L., Fu, Y., (2012) Angew. Chem. Int. Ed., 51, p. 12551
  • Parsons, A.T., Senecal, T.D., Buchwald, S.L., (2012) Angew. Chem. Int. Ed., 51, p. 2947
  • Xu, J., Fu, Y., Luo, D.-F., Jiang, Y.-Y., Xiao, B., Liu, Z.-J., Gong, T.-J., Liu, L., (2011) J. Am. Chem. Soc., 133, p. 15300
  • Novak, P., Lishchynskyi, A., Grushin, V.V., (2012) J. Am. Chem. Soc., 134, p. 16167
  • Zanardi, A., Novikov, M.A., Benet-Buchholz, M.E., Grushin, V.V., (2011) J. Am. Chem. Soc., 133, p. 20901
  • Malosh, C.F., Ready, J.M., (2004) J. Am. Chem. Soc., 126, p. 10240
  • Mao, Z., Huang, F., Yu, H., Chen, J., Yu, Z., Xu, Z., (2014) Chem. Eur. J., 20, p. 3439
  • Xu, J., Liu, X., Fu, Y., (2014) Tetrahedron Lett., 55, p. 585
  • Nagib, D.A., Scott, M.E., MacMillan, D.W.C., (2009) J. Am. Chem. Soc., 131, p. 10875
  • Iqbal, N., Choi, S., Kim, E., Jin Cho, E., (2012) J. Org. Chem., 77, p. 11383
  • Merino, E., Nevado, C., (2014) Chem. Soc. Rev., 43, p. 6598
  • Lin, J.-S., Liu, X.-G., Zhu, X.-L., Tan, B., Liu, X.-Y., (2014) J. Org. Chem., 79, p. 7084
  • Dubbaka, S.R., Nizalapur, S., Atthunuri, A.R., Salla, M., Mathew, T., (2014) Tetrahedron, 70, p. 2118
  • Jin Cho, E., Buchwald, S.L., (2011) Org. Lett., 13, p. 6552
  • Zhu, J., Zhang, W., Zhang, L., Liu, J., Zheng, J., Hu, J., (2010) J. Org. Chem., 75, p. 5505
  • Chu, L., Qing, F.-L., (2010) J. Am. Chem. Soc., 132, p. 7262
  • Maiji, A., Hazra, A., Maiti, D., (2014) Org. Lett., 16, p. 4524
  • Hwang, J., Park, K., Choe, J., Min, H., Song, K.H., Lee, S., (2014) J. Org. Chem., 79, p. 3267
  • Xu, S., Chen, H.-H., Dai, J.-J., Xu, H.-J., (2014) Org. Lett., 16, p. 2306
  • Feng, Y.-S., Xie, C.-Q., Qiao, W.-L., Xu, H.-J., (2013) Org. Lett., 15, p. 936
  • Chinchilla, R., Najera, C., (2007) Chem. Rev., 107, p. 874
  • Soheili, A., Albaneze-Walker, J., Murry, J.A., Dormer, P.G., Hughes, D.L., (2003) Org. Lett., 5, p. 4191
  • Garcia-Melchor, M., Pacheco, M.C., Najera, C., Lledos, A., Ujaque, G., (2012) ACS Catal., 2, p. 135
  • Shang, R., Yang, Z.-W., Wang, Y., Zhang, S.-L., Liu, L., (2010) J. Am. Chem. Soc., 132, p. 14391
  • Kosobokov, M.D., Levin, V.V., Struchkova, M.I., Dilman, A.D., (2014) Org. Lett., 16, p. 3784
  • Li, L., Wang, F., Ni, C., Hu, J., (2013) Angew. Chem. Int. Ed., 52, p. 12390
  • Rubiales, G., Alonso, C., Martínez de Marigorta, E., Palacios, F., (2014) ARKIVOC II, p. 362
  • Wakita, N., Hara, S., (2014) Heterocycles, 88, p. 1201
  • Sato, K., Yuki, T., Yamaguchi, R., Hamano, T., Tarui, A., Omote, M., Kumadaki, I., Ando, A., (2009) J. Org. Chem., 74, p. 3815
  • Lu, Y., Li, Y., Zhang, R., Jin, K., Duan, C., (2014) J. Fluorine Chem., 161, p. 128
  • Herrmann, A.T., Smith, L.L., Zakarian, A., (2012) J. Am. Chem. Soc., 134, p. 6976
  • Jiang, H., Huang, C., Guo, J., Zeng, C., Zhang, Y., Yu, S., (2012) Chem. Eur. J., 18, p. 15158
  • Liu, J., Zhuang, S., Gui, Q., Chen, X., Yang, Z., Tan, Z., (2014) Eur. J. Org. Chem.
  • Wang, X., Xu, Y., Deng, Y., Zhou, Y., Feng, J., Ji, G., Zhang, Y., Wang, J., (2014) Chem. Eur. J., 20, p. 961
  • Hu, M., He, Z., Gao, B., Li, L., Ni, C., Hu, J., (2013) J. Am. Chem. Soc., 135, p. 17302
  • Hu, M., Ni, C., Hu, J., (2012) J. Am. Chem. Soc., 134, p. 15257

Citas:

---------- APA ----------
Lantaño, B., Torviso, M.R., Bonesi, S.M., Barata-Vallejo, S. & Postigo, A. (2015) . Advances in metal-assisted non-electrophilic fluoroalkylation reactions of organic compounds. Coordination Chemistry Reviews, 285, 76-108.
http://dx.doi.org/10.1016/j.ccr.2014.11.004
---------- CHICAGO ----------
Lantaño, B., Torviso, M.R., Bonesi, S.M., Barata-Vallejo, S., Postigo, A. "Advances in metal-assisted non-electrophilic fluoroalkylation reactions of organic compounds" . Coordination Chemistry Reviews 285 (2015) : 76-108.
http://dx.doi.org/10.1016/j.ccr.2014.11.004
---------- MLA ----------
Lantaño, B., Torviso, M.R., Bonesi, S.M., Barata-Vallejo, S., Postigo, A. "Advances in metal-assisted non-electrophilic fluoroalkylation reactions of organic compounds" . Coordination Chemistry Reviews, vol. 285, 2015, pp. 76-108.
http://dx.doi.org/10.1016/j.ccr.2014.11.004
---------- VANCOUVER ----------
Lantaño, B., Torviso, M.R., Bonesi, S.M., Barata-Vallejo, S., Postigo, A. Advances in metal-assisted non-electrophilic fluoroalkylation reactions of organic compounds. Coord. Chem. Rev. 2015;285:76-108.
http://dx.doi.org/10.1016/j.ccr.2014.11.004