Navegar

Colección

Datos Estadísticas

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:

(Chemical Equation Presented) No loss, no gain: In the synthesis of biaryls either the electrophilic or nucleophilic partner can be replaced by a substrate with a carbon-based leaving group (see scheme). Whereas replacing the electrophilic unit is not worthwhile, the use of nucleophiles with a C-based leaving group has decisive advantages. © 2008 Wiley-VCH Verlag GmbH & Co. KGaA.

Registro:

Documento: Artículo
Título:Biaryl formation involving carbon-based leaving groups: Why not?
Autor:Bonesi, S.M.; Fagnoni, M.; Albini, A.
Filiación:CIHIDECAR-CONICET, Departamento de Química Orgánica, Universidad de Buenos Aires, 1428, Buenos Aires, Argentina
Department of Organic Chemistry, University of Pavia, Italy
Palabras clave:Arylation; Biphenyls; C-C activation; C-C coupling; Leaving groups; Chemical reactions; Synthesis (chemical); Arylation; Biphenyls; C-C activation; C-C coupling; Leaving groups; Aromatic compounds; aromatic hydrocarbon; biological product; bromide; carbon; carboxylic acid; drug; methanol; chemistry; review; synthesis; Biological Products; Bromides; Carbon; Carboxylic Acids; Hydrocarbons, Aromatic; Methanol; Pharmaceutical Preparations
Año:2008
Volumen:47
Número:52
Página de inicio:10022
Página de fin:10025
DOI: http://dx.doi.org/10.1002/anie.200803777
Título revista:Angewandte Chemie - International Edition
Título revista abreviado:Angew. Chem. Int. Ed.
ISSN:14337851
CODEN:ACIEA
CAS:bromide, 24959-67-9; carbon, 7440-44-0; methanol, 67-56-1; Biological Products; Bromides; Carbon, 7440-44-0; Carboxylic Acids; Hydrocarbons, Aromatic; Methanol, 67-56-1; Pharmaceutical Preparations
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_14337851_v47_n52_p10022_Bonesi

Referencias:

  • Stanforth, S.P., (1998) Tetrahedron, 54, pp. 263-303
  • Alberico, D., Scott, M.E., Lautens, M., (2007) Chem. Rev, 107, pp. 174-238
  • Galli, C., Pau, T., (1998) Tetrahedron, 54, pp. 2893-2904
  • Takagi, T., Mikami, N., Matsuda, T., Miyamoto, J., (1989) J. Chem. Soc. Perkin Trans. 2, pp. 779-782
  • Galli, C., Gentili, P., (1998) Acta Chem. Scand, 52, pp. 67-76
  • Frolov, A.N., (1998) Russ. J. Org. Chem, 34, pp. 139-161
  • A notable case among the carbon-based leaving groups is the migration of alkyl groups (mainly tertiary) in alkylbenzenes by a dealkylation/alkylation sequence under Friedel-Crafts catalysis; Tobisu, M., Chatani, N., (2008) Chem. Soc. Rev, 37, pp. 300-307
  • Miller, J.A., (2001) Tetrahedron Lett, 42, pp. 6991-6993
  • Miller, J.A., Dankwardt, J.W., Penny, J.A., (2003) Synthesis, 11, pp. 1643-1648
  • Penny, J.M., Miller, J.A., (2004) Tetrahedron Lett, 45, pp. 4989-4992
  • Miller, J.A., Dankwardt, J.W., (2003) Tetrahedron Lett, 44, pp. 1907-1910
  • Ackermann, L., Born, R., Spatz, J.H., Meyer, D., (2005) Angew. Chem, 117, pp. 7382-7386. , See for example
  • (2005) Angew. Chem. Int. Ed, 44, pp. 7216-7219
  • Terao, Y., Wakui, H., Satoh, T., Miura, M., Nomura, M., (2001) J. Am. Chem. Soc, 123, pp. 10407-10408
  • Terao, Y., Wakui, H., Nomoto, M., Satoh, T., Miura, M., Nomura, M., (2003) J. Org. Chem, 68, pp. 5236-5243
  • Yokooji, A., Satoh, T., Miura, M., Nomura, M., (2004) Tetrahedron, 60, pp. 6757-6763
  • Bíró, A.B., Kotschy, A., (2007) Eur. J. Org. Chem, pp. 1364-1368
  • Nakano, M., Satoh, T., Miura, M., (2006) J. Org. Chem, 71, pp. 8309-8311
  • Gooßen, L.J., Deng, G., Levy, L.M., (2006) Science, 313, pp. 662-664
  • Gooßen, L.J., Rodriguez, N., Melzer, B., Linder, C., Deng, G., Levy, L.M., (2007) J. Am. Chem. Soc, 129, pp. 4824-4833
  • Gooßen, L.J., Rodríguez, N., Gooßen, K., (2008) Angew. Chem, 120, pp. 3144-3164
  • (2008) Angew. Chem. Int. Ed, 47, pp. 3100-3120
  • Gooßen, L.J., Zimmermann, B., Knauber, T., (2008) Angew. Chem, 120, pp. 7211-7214
  • (2008) Angew. Chem. Int. Ed, 47, pp. 7103-7106
  • Becht, J.-M., Catala, C., Le Drian, C., Wagner, A., (2007) Org. Lett, 9, pp. 1781-1783
  • Gooßen, L.J., Rudolphi, F., Oppel, C., Rodríguez, N., (2008) Angew. Chem, 120, pp. 3085-3088
  • (2008) Angew. Chem. Int. Ed, 47, pp. 3043-3045
  • Forgione, P., Brochu, M.-C., St-Onge, M., Thesen, K.H., Bailey, M.D., Bilodeau, F., (2006) J. Am. Chem. Soc, 128, pp. 11350-11351
  • Gooßen, L.J., Melzer, B., (2007) J. Org. Chem, 72, pp. 7473-7476

Citas:

---------- APA ----------
Bonesi, S.M., Fagnoni, M. & Albini, A. (2008) . Biaryl formation involving carbon-based leaving groups: Why not?. Angewandte Chemie - International Edition, 47(52), 10022-10025.
http://dx.doi.org/10.1002/anie.200803777
---------- CHICAGO ----------
Bonesi, S.M., Fagnoni, M., Albini, A. "Biaryl formation involving carbon-based leaving groups: Why not?" . Angewandte Chemie - International Edition 47, no. 52 (2008) : 10022-10025.
http://dx.doi.org/10.1002/anie.200803777
---------- MLA ----------
Bonesi, S.M., Fagnoni, M., Albini, A. "Biaryl formation involving carbon-based leaving groups: Why not?" . Angewandte Chemie - International Edition, vol. 47, no. 52, 2008, pp. 10022-10025.
http://dx.doi.org/10.1002/anie.200803777
---------- VANCOUVER ----------
Bonesi, S.M., Fagnoni, M., Albini, A. Biaryl formation involving carbon-based leaving groups: Why not?. Angew. Chem. Int. Ed. 2008;47(52):10022-10025.
http://dx.doi.org/10.1002/anie.200803777