Artículo

Estamos trabajando para incorporar este artículo al repositorio
Consulte el artículo en la página del editor
Consulte la política de Acceso Abierto del editor

Abstract:

Perfluoroalkylation of alkenes and alkynes was performed using thermal initiation by ACCN (1,1′-azobis(cyclohexanecarbonitrile)) in water, with good yields. The procedure is simple and more ecofriendly that most of the methods published for the synthesis of related compounds. Using water (without any cosolvent or metal catalysts), it allows the synthesis of the addition products with medium to high yields. ©ARKAT-USA, Inc.

Registro:

Documento: Artículo
Título:Perfluoroalkylation of alkenes and alkynes in water
Autor:Vázquez, A.J.; Nudelman, N.S.
Filiación:Depto. Química Orgánica, Facultad de Ciencias Exactas Y Naturales, Universidad de Buenos Aires, Buenos Aires, 1428, Argentina
Palabras clave:Perfluoroalkylation; Radical addition; Reactions in water; Thermal initiation
Año:2015
Volumen:2015
Número:5
Página de inicio:190
Página de fin:201
DOI: http://dx.doi.org/10.3998/ark.5550190.p009.091
Título revista:Arkivoc
Título revista abreviado:Arkivoc
ISSN:15517004
CODEN:AGFUA
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_15517004_v2015_n5_p190_Vazquez

Referencias:

  • Rahman, M.F., Peldszus, S., Anderson, W.B., (2014) Water Research, 50, pp. 318-340
  • Fukuda, S., Chaussy, D., Belgacem, M.N., Reverdy-Bruas, N., Thielemans, W., (2013) Applied Surface Science, 277, pp. 57-66. , http://dx.doi.org/10.1016/j.apsusc.2013.03.174
  • Jaoued-Grayaa, N., Boughariou-Charrada, B., Hedhli, A., (2014) J. Surfactants and Detergents, 17, pp. 767-772. , http://dx.doi.org/10.1007/s11743-013-1509-6
  • Coope, T., Moloy, K., Yake, A., Petrov, V., Taylor, C., Hung, M., Peng, S., (2014) J. Fluorine Chem, 161, pp. 41-50. , http://dx.doi.org/10.1016/j.jfluchem.2014.01.022
  • Hori, H., Saito, H., Sakai, H., Kitahara, T., Sakamoto, T., (2014) Chemosphere, , in press
  • Park, J.-M., Lee, Y.-H., Park, H., Kim, H.-D., (2014) J. Applied Polymer Sci, 131, p. 40603. , http://dx.doi.org/10.1002/app.40603
  • Li, Y., Su, Y., Zhao, X., Zhang, R., Zhao, J., Fan, X., Jiang, Z., (2014) J. Membrane Sci, 455, pp. 15-23. , http://dx.doi.org/10.1016/j.memsci.2013.12.060
  • Zhu, X., Guo, S., Jañczewski, D., Parra Velandia, S.J., Teo, S.L.-M., Vancso, G.J., (2014) Langmuir, 30, pp. 288-296. , http://dx.doi.org/10.1021/la404300r
  • Yan, Z., Liu, W., Wang, H., Su, K., Xia-Hou, G., (2014) J. Fluorine Chem, 157, pp. 63-72. , http://dx.doi.org/10.1016/j.jfluchem.2013.11.008
  • Mikhaylov, D.Y., Budnikova, Y.H., (2013) Russ. Chem. Rev., 82, pp. 835-864. , http://dx.doi.org/10.1070/RC2013v082n09ABEH004342
  • Xiao, Z., Hu, H., Ma, J., Chen, Q., Guo, Y., (2013) Chinese J. Chem., 31, pp. 939-944. , http://dx.doi.org/10.1002/cjoc.201300433
  • Wallentin, C.-J., Nguyen, J.D., Finkbeiner, P., Stephenson, C.R.J., (2012) J. Am. Chem. Soc., 134, pp. 8875-8884. , http://dx.doi.org/10.1021/ja300798k
  • Xu, T., Cheung, C.W., Hu, X., (2014) Angew. Chem. - Int. Ed., 53, pp. 4910-4914. , http://dx.doi.org/10.1002/anie.201402511
  • Takagi, T., Kanamori, T., (2011) J. Fluorine Chem, 132, pp. 427-429. , http://dx.doi.org/10.1016/j.jfluchem.2011.03.001
  • Yahima, T., (2013) J. Synthetic Org. Chem, 71, pp. 683-693. , http://dx.doi.org/10.5059/yukigoseikyokaishi.71.683
  • Yahima, T., Jahan, I., Tonoi, T., Shinmen, M., Nishikawa, A., Yamaguchi, K., Sekine, I., Nagano, H., (2012) Tetrahedron, 68, pp. 6856-6861. , http://dx.doi.org/10.1016/j.tet.2012.06.028
  • Hamlin, T.A., Kelly, C.B., Cywar, R.M., Leadbeater, N.E., (2014) J. Org. Chem., 79, pp. 1145-1155. , http://dx.doi.org/10.1021/jo402577n
  • Gladow, D., Reissig, H.-U., (2014) J. Org. Chem., 79, pp. 4492-4502. , http://dx.doi.org/10.1021/jo500534t
  • Mormino, M.G., Fier, P.S., Hartwig, J.F., (2014) Org. Lett., 16, pp. 1744-1747. , http://dx.doi.org/10.1021/ol500422t
  • Cao, L., Shen, D., Wei, J., Chen, J., Deng, H., Shao, M., Shi, J., Cao, W., (2014) European J. Org. Chem., pp. 2460-2467. , http://dx.doi.org/10.1002/ejoc.201400056
  • Kolvari, E., Zolfigol, M.A., Peiravi, M., (2012) Green Chem. Lett. & Rev., 5, pp. 155-159. , http://dx.doi.org/10.1080/17518253.2011.606849
  • Roy, S., Bhar, S., (2010) Green Chem. Lett. & Rev., 3, pp. 341-347. , http://dx.doi.org/10.1080/17518253.2010.491095
  • Banitaba, S.H., Safari, J., Khalili, S.D., (2013) Ultrasonic Sonochem, 20, pp. 401-407. , http://dx.doi.org/10.1016/j.ultsonch.2012.07.007
  • Postigo, A., Nudelman, N.S., (2011) Coord. Chem. Rev., 255, pp. 2991-3030. , http://dx.doi.org/10.1016/j.ccr.2011.07.015
  • Slodowicz, M., Barata-Vallejo, S., Vázquez, A., Nudelman, N.S., Postigo, A., (2012) J. Fluorine Chem, 135, pp. 137-143. , http://dx.doi.org/10.1016/j.ccr.2011.07.015
  • Bravo, A., Bjorsvik, H.-R., Fontana, F., Liguori, L., Mele, A., Minisci, F., (1997) J. Org. Chem., 62, pp. 7128-7136. , http://dx.doi.org/10.1021/jo970302s
  • Brace, N.O.J., (1999) Fluorine Chem, 93, pp. 1-25
  • Tsuchii, K., Imura, M., Kamada, N., Hirao, T., Ogawa, A., (2004) J. Org. Chem., 69, pp. 6658-6665. , http://dx.doi.org/10.1021/jo0495889
  • Fang, X., Yang, X., Yang, X., Mao, S., Wang, Z., Chen, G., Wu, F., (2007) Tetrahedron, 63, pp. 10684-10692. , http://dx.doi.org/10.1016/j.tet.2007.07.087
  • Liu, S.Q., Wang, S.W., Qing, F.-L., (2005) J. Fluorine Chem, 126, pp. 771-778. , http://dx.doi.org/10.1016/j.jfluchem.2005.02.011
  • Wu, F., Yang, X., Wang, Z., Huang, W., (2007) J. Fluorine Chem, 128, pp. 84-86. , http://dx.doi.org/10.1016/j.jfluchem.2006.10.001
  • Habib, M.H., Mallouk, T.E., (1991) J. Fluorine Chem, 53, pp. 53-60. , http://dx.doi.org/10.1016/S0022-1139(00)82238-1

Citas:

---------- APA ----------
Vázquez, A.J. & Nudelman, N.S. (2015) . Perfluoroalkylation of alkenes and alkynes in water. Arkivoc, 2015(5), 190-201.
http://dx.doi.org/10.3998/ark.5550190.p009.091
---------- CHICAGO ----------
Vázquez, A.J., Nudelman, N.S. "Perfluoroalkylation of alkenes and alkynes in water" . Arkivoc 2015, no. 5 (2015) : 190-201.
http://dx.doi.org/10.3998/ark.5550190.p009.091
---------- MLA ----------
Vázquez, A.J., Nudelman, N.S. "Perfluoroalkylation of alkenes and alkynes in water" . Arkivoc, vol. 2015, no. 5, 2015, pp. 190-201.
http://dx.doi.org/10.3998/ark.5550190.p009.091
---------- VANCOUVER ----------
Vázquez, A.J., Nudelman, N.S. Perfluoroalkylation of alkenes and alkynes in water. Arkivoc. 2015;2015(5):190-201.
http://dx.doi.org/10.3998/ark.5550190.p009.091