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Abstract:

In this review non-carbon-centered radicals are used in water and aqueous mixtures to induce and accomplish several synthetically useful organic transformations such as Reformatsky reactions, alkylation and allylation reactions of carbonyl compounds, electron deficient alkenes and imine derivatives, radical conjugate additions, metal-mediated radical cyclizations, reductive cross coupling reactions and other coupling reactions, oxidation and reduction reactions in water. In doing so, the array of metal radicals used encompass elements from the main groups (IIIB, IVB, VB and VIB groups), as well as transition metals. However, the important class of radical hydrometallation reactions of carbon-carbon multiple bonds in water is not the subject of this work. © 2011 Elsevier B.V.

Registro:

Documento: Artículo
Título:Synthetically useful metal-mediated radical transformations in water and aqueous media
Autor:Postigo, A.; Nudelman, N.S.
Filiación:Departamento de Química Orgánica, Facultad de Farmacia y Bioquímica, Universidad de Buenos Aires, Junín 954, CP 1113, Buenos Aires, Argentina
Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Ciudad Universitaria, Pabellón II, 3er piso, CP 1428 Buenos Aires, Argentina
Palabras clave:Metal radicals in water; Metal-mediated radical alkylation and allylation reactions in water; Metal-mediated radical cyclizations in water; Metal-mediated radical reductions and oxidations in water; Metal-mediated reductive cross coupling in water
Año:2011
Volumen:255
Número:23-24
Página de inicio:2991
Página de fin:3030
DOI: http://dx.doi.org/10.1016/j.ccr.2011.07.015
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_v255_n23-24_p2991_Postigo

Referencias:

  • Nair, V., Ros, S., Jayan, C.N., Pillai, B.S., (2004) Tetrahedron, 60, p. 1959
  • Iqbal, J., Bhatia, B., Nayyar, N.K., (1994) Chem. Rev., 94, p. 519
  • Weaver, J.D., Recio, A., Grenning, A.J., Tunge, J.A., (2011) Chem. Rev., 111, p. 1846
  • Yadav, J.S., Antony, A., George, J., Reddy, B.V.S., (2010) Eur. J. Org. Chem., 4, p. 591
  • Litwinienko, G., Ingold, K.U., (2007) Acc. Chem. Res., 40, p. 222
  • Butler, R.N., Coyne, A.G., (2010) Chem. Rev., 110, p. 6302
  • Barata-Vallejo, S., Nudelman, N., Postigo, A., (2011) Curr. Org. Chem., 15, p. 1826
  • lngold, K.U., (1997) Pure Appl. Chem., 69, p. 241
  • Litwinienko, G., DiLabio, G.A., Mulder, P., Korth, H.-G., Ingold, K.U., (2009) J. Phys. Chem. A, 113, p. 6275
  • Nielsen, M.F., Ingold, K.U., (2006) J. Am. Chem. Soc., 128, p. 1172
  • Snelgrove, D.W., Lusztyk, J., Banks, J.T., Mulder, P., Ingold, K.U., (2001) J. Am. Chem. Soc., 123, p. 469
  • Avila, D.V., Ingold, K.U., (1995) J. Am. Chem. Soc., 117, p. 2929
  • Li, C.-J., (2005) Chem. Rev., 105, p. 3095
  • Yet, L., (2000) Chem. Rev., 100, p. 2963
  • Dermican, A., Parsons, P.J., (2003) Eur. J. Org. Chem., p. 1729
  • Miyabe, H., Ueda, M., Fujii, K., Goto, T., Naito, T., (2003) J. Org. Chem., 68, p. 5618
  • Miyabe, H., Fujii, K., Goto, T., Naito, T., (2000) Org. Lett., 2, p. 4071
  • Miyabe, H., Fujii, K., Tanaka, H., Naito, T., (2001) Chem. Commun., p. 831
  • Ueda, M., Miyabe, H., Nishimura, A., Miyata, O., Takemoto, Y., Naito, T., (2003) Org. Lett., 5, p. 3835
  • Majumdar, K.C., Basu, P.K., Mukhopadhyay, P.P., (2004) Tetrahedron, 60, p. 6239
  • Perchyonok, V.T., Lykakis, I.N., (2009) Curr. Org. Chem., 13, p. 573
  • Bailey, W.F., Carson, M.W., (1998) J. Org. Chem., 63, p. 361
  • Kobayashi, S., Mori, Y., Fossey, J.S., Salter, M.M., (2011) Chem. Rev., , doi:10.1021/cr100204f, Article ASAP
  • Friestad, G., Mathies, A.K., (2007) Tetrahedron, 63, p. 2541
  • Sakuma, D., Togo, H., (2005) Tetrahedron, 61, p. 10138
  • Foulon, J.P., Normant, F., Connerçon, M.B., (1982) J. Organomet. Chem., 228, p. 321
  • Gocmen, M., Soussan, G., Freón, P., (1973) Bull. Soc. Chem. Fr., 40, p. 1310
  • Normant, J.F., Chuit, C., Foulon, J.P., (1981) Tetrahedron, 37, p. 1385
  • Cahiez, G., Alami, M., (1989) Tetrahedron Lett., 30, p. 7365
  • Wipf, P., Xu, W., Smitrovich, J.H., Lehmann, R., Venanzi, L.M., (1994) Tetrahedron, 50, p. 1935
  • Dieter, R.K., Alexander, C.W., Nice, L.E., (2000) Tetrahedron, 56, p. 2767
  • Maruoka, K., Imoto, H., Saito, S., Yamamoto, H., (1994) J. Am. Chem. Soc., 116, p. 4131
  • Brown, H.C., Midland, M.M., (1971) J. Am. Chem. Soc., 93, p. 1506
  • Yeung, D.W.K., Warkentin, J., (1980) Can. J. Chem., 58, p. 2386
  • Russell, G.A., Shi, Z., Jiang, W., Hu, S., Kim, B.H., Baik, W., (1995) J. Am. Chem. Soc., 117, p. 3952
  • Petrier, C., Dupuy, C., Luche, J.-L., (1986) Tetrahedron Lett., 27, p. 3149
  • Luche, J.-L., Allavena, C., (1988) Tetrahedron Lett., 29, p. 5369
  • Dupuy, C., Petrier, C., Sarandeses, L.A., Luche, J.-L., (1991) Synth. Commun., 21, p. 643
  • Luche, J.-L., Allavena, C., Petrier, C., Dupuy, C., (1988) Tetrahedron Lett., 29, p. 5373
  • Blanchard, P., El Kortbi, M.S., Fourrey, J.-L., Robert-Gero, M., (1992) Tetrahedron Lett., 33, p. 3319
  • Raussou, S., Urbain, N., Mangeney, P., Alexakis, A., Platzer, N., (1996) Tetrahedron Lett., 37, p. 1599
  • Mangeney, P., Hamon, L., Raussou, S., Urbain, N., Alexakis, A., (1998) Tetrahedron, 54, p. 10349
  • Marshall, J.A., Robinson, E.D., (1990) J. Org. Chem., 55, p. 3450
  • Marshall, J.A., Wang, X.J., (1991) J. Org. Chem., 56, p. 960
  • Marshall, J.A., Sehon, C.A., (1995) J. Org. Chem., 60, p. 5966
  • Marshall, J.A., Bartley, G.S., (1994) J. Org. Chem., 59, p. 7169
  • Hashmi, A.S.K., Schwarz, L., Bats, J.W., (2000) J. Prakt. Chem., 342, p. 40
  • Panchaud, P., Renaud, P., (2004) J. Org. Chem., 69, p. 3205
  • Sugi, M., Sakuma, D., Togo, H., (2003) J. Org. Chem., 68, p. 7629
  • Yang, D., Yan, Y.-L., Zheng, B.-F., Gao, Q., Zhu, N., (2006) Org. Lett., 8, p. 5757
  • Clark, A.J., Wilson, P., (2008) Tetrahedron Lett., 49, p. 4848
  • Bull, J.A., Hutchings, M.G., Luján, C., Quayle, P., (2008) Tetrahedron Lett., 49, p. 1352
  • Guelphi, F., Roncaglia, F., Pattarozzi, M., Giangiordano, V., Petrillo, G., Sancassan, F., Parsons, A.F., (2009) Tetrahedron, 65, p. 10323
  • Cao, L., Li, C., (2008) Tetrahedron Lett., 49, p. 7380
  • Majumdar, K.C., Debnath, P., (2008) Tetrahedron, 64, p. 9799
  • Chen, H.-L., Lin, C.-Y., Cheng, Y.-C., Tsai, A.-I., Chuang, C.-P., (2005) Synthesis, p. 977
  • Hawthorne, M.F., Reintjes, M., (1965) J. Am. Chem. Soc., 87, p. 4585
  • Kabalka, G.W., (1971) J. Organomet. Chem., 33, pp. C25
  • Tsuchiya, Y., Izumisawa, Y., Togo, H., (2009) Tetrahedron, 65, p. 7533
  • Khan, F.A., Satapathy, F., Dash, J., Savitha, G., (2004) J. Org. Chem., 69, p. 5295
  • Kim, B.H., Jim, Y., Jum, Y.M., Han, R., Baik, W., Lee, B.M., (2000) Tetrahedron Lett., 41, p. 2137
  • Russell, G.A., Jawdosiuk, M., Makosza, M., (1979) J. Am. Chem. Soc., 101, p. 2355
  • Russell, G.A., Metcalfe, A.R., (1979) J. Am. Chem. Soc., 101, p. 2359
  • Russell, G.A., Mydryk, B., (1982) J. Org. Chem., 47, p. 1879
  • Russell, G.A., Baik, W., (1988) J. Chem. Soc., Chem. Commun., p. 196
  • Postigo, A., Rossi, R.A., (2003) Curr. Org. Chem., 7, p. 747
  • Rossi, R.A., Pierini, A.B., Peñeñory, A.B., (2003) Chem. Rev., 103, p. 71
  • Haberman, J.X., Li, C.-J., (1997) Tetrahedron Lett., 38, p. 4735
  • Li, C.-J., Chen, D.-L., Lu, Y.-Q., Haberman, J.X., Mague, J.T., (1996) J. Am. Chem. Soc., 118, p. 4216
  • Claessens, S., Jacobs, J., Aeken, S.V., Tehrani, K.A., Kimpe, N.D., (2008) J. Org. Chem., 73, p. 7555
  • Estévez, R.E., Oller-López, J.L., Robles, R., Melgarejo, C.R., Gansauer, A., Cuerva, J.M., Oltra, J.E., (2006) Org. Lett., 8, p. 5433
  • RajanBabu, T.V., Nugent, W.A., (1994) J. Am. Chem. Soc., 116, p. 986. , For pioneering work on Ti(III)-promoted transformations see:
  • Postigo, A., Kopsov, S., Ferreri, C., Chatgilialoglu, C., (2007) Org. Lett., 9, p. 5159
  • Shaabani, A., Maleki, A., (2008) Chem. Pharm. Bull., 56, p. 79
  • Postigo, A., (2011) Organic Radical Reactions in Water and Alternative Media, , Nova Science Publications, Happaauge, New York, Al Postigo (Ed.)
  • Calandra, J., Postigo, A., Russo, D., Sbarbati-Nudelman, N., Tereñas, J.J., (2010) J. Phys. Org. Chem., 23, p. 944
  • Barata-Vallejo, S., Postigo, A., (2010) J. Org. Chem., 75, p. 6141
  • Ocampo, R., Dolbier, W.R., (2004) Tetrahedron, 60, p. 9325
  • Li, C.-J., (1996) Tetrahedron, 52, p. 5643
  • Li, C.-J., (1993) Chem. Rev., 93, p. 2023
  • Bieber, W.L., Malvestiti, I., Storch, E.C., (1997) J. Org. Chem., 62, p. 9061
  • Chan, T.H., Li, C.-J., Wei, Z.Y., (1994) Can. J. Chem., 72, p. 1181
  • Kagan, H.B., (2003) Tetrahedron, 59, p. 10372
  • Keh, C.C.K., Wei, C., Li, C.-J., (2003) J. Am. Chem. Soc., 125, p. 4062
  • Arimitsu, S., Jacobsen, J.M., Hammond, G.B., (2007) Tetrahedron Lett., 48, p. 1625
  • Arimitsu, S., Hammod, G.B., (2006) J. Org. Chem., 71, p. 8665
  • Cannella, R., Clerici, A., Pastori, N., Regolini, E., Porta, O., (2005) Org. Lett., 7, p. 645
  • Bieber, L.W., Storch, E.C., Malvestiti, I., da Silva, M.F., (1998) Tetrahedron Lett., 39, p. 9393
  • Shen, Z.-L., Loh, T.-P., (2007) Org. Lett., 9, p. 5413
  • Friestad, G.K., (2001) Tetrahedron, 57, p. 5461
  • Miyabe, H., Ueda, M., Naito, T., (2000) J. Org. Chem., 65, p. 5043
  • Miyabe, M., Ueda, M., Nishimura, A., Naito, T., (2004) Tetrahedron, 60, p. 4227
  • Miyabe, H., Ueda, M., Nishimura, A., Naito, T., (2002) Org. Lett., 4, p. 131
  • Yang, Y.-S., Shen, Z.-L., Loh, T.-P., (2009) Org. Lett., 11, p. 1209
  • Ueda, M., (2004) Yakagaku Zasshi., 124, p. 311
  • Ueda, M., Miyabe, H., Miyata, O., Naito, T., (2009) Tetrahedron, 65, p. 1321
  • Srikanth, G.S.C., Castle, S.L., (2005) Tetrahedron, 61, p. 10377
  • Jang, D.O., Cho, D.H., Chung, C.-M., (2001) Synlett, p. 1923
  • Jang, D.O., Cho, D.H., (2002) Synlett, p. 1523
  • Cho, D.H., Jang, D.O., (2005) Tetrahedron Lett., 46, p. 1799
  • Mascareñas, J.L., Perez-Sestelo, J., Castedo, L., Mouriño, A., (1991) Tetrahedron Lett., 32, p. 2813
  • Perez Sestelo, J., Mascareñas, J.L., Castedo, L., Mouriño, A., (1993) J. Org. Chem., 58, p. 118
  • Perez-Sestelo, J., Mascareñas, J.L., Castedo, L., Mouriño, A., (1994) Tetrahedron Lett., 35, p. 275
  • Suarez, R.M., Perez Sestelo, J., Sarandeses, L.A., (2002) Synlett, p. 1435
  • Suarez, R.M., Perez Sestelo, J., Sarandeses, L.A., (2003) Chem. Eur. J., 9, p. 4179
  • Suarez, R.M., Perez Sestelo, J., Sarandeses, L.A., (2004) Org. Biomol. Chem., 2, p. 3584
  • Perez Sestelo, J., Cornella, I., de Uña, O., Mouriño, A., Sarandeses, L.A., (2002) Chem. Eur. J., 8, p. 2747
  • Perez Sestelo, J., de Uña, O., Mouriño, A., Sarandeses, L.A., (2002) Synlett, p. 719
  • Cornella, I., Suarez, R.M., Mouriño, A., Perez Sestelo, J., Sarandeses, L.A., (2004) J. Steroid Biochem. Mol. Biol., p. 89
  • Cornella, I., Perez Sestelo, J., Mouriño, A., Sarandeses, L.A., (2002) J. Org. Chem., 67, p. 4707
  • Miura, K., Tomita, M., Ichikawa, J., Hosomi, A., (2008) Org. Lett., 10, p. 133
  • Movassagh, B., Navidi, M., (2008) Tetrahedron Lett., 49, p. 6712
  • Li, C.-J., Meng, Y., Yi, X.H., (1998) J. Org. Chem., 63, p. 7498
  • Li, C.-J., Chan, T.H., (1991) Organometallics, 10, p. 2548
  • Wada, M., Ohki, H., Akiba, K.-Y., (1987) J. Chem. Soc., Chem. Commun., p. 708
  • Bonini, B.F., Comes-Franchini, M., Fochi, M., Mazzanti, G., Nanni, C., Ricci, A., (1998) Tetrahedron Lett., 39, p. 6737
  • Fukuma, T., Lock, S., Miyoshi, N., Wada, M., (2002) Chem. Lett., p. 376
  • Li, L.-H., Chan, T.H., (2000) Tetrahedron Lett., 41, p. 5009
  • Zhou, J.Y., Jia, Y., Sun, G.F., Wu, S.H., (1997) Synth. Commun., 27, p. 1899
  • Chan, T.H., Yang, Y., (1999) Tetrahedron Lett., 40, p. 3863
  • Cintas, P., (1995) Synlett, p. 1087
  • Zhang, W.-C., Li, C.-J., (1999) J. Org. Chem., 64, p. 3230
  • Lawrence, L.M., Whitesides, G.M., (1980) J. Am. Chem. Soc., 102, p. 2493
  • Walborsky, H.M., Zimmermann, C., (1992) J. Am. Chem. Soc., 114, p. 4996
  • Alexander, E.R., (1950) Principles of Ionic Organic Reactions, p. 188. , John Wiley & Sons
  • Hygum Dam, J., Fristrup, P., Madsen, R., (2008) J. Org. Chem., 73, p. 3228
  • Li, C.-J., Meng, Y., Yi, X.-H., (1997) J. Org. Chem., 62, p. 8632
  • Chan, T.H., Isaac, B.M., (1996) Pure Appl. Chem., 68, p. 919
  • Nokami, J., Otera, J., Sudo, T., Okawara, R., (1983) Organometallics, 2, p. 191
  • Nokami, J., Wakabayashi, S., Okawara, R., (1984) Chem. Lett., p. 869
  • Wu, S.H., Huang, B.Z., Zhu, T.M., Yiao, D.Z., Chu, Y.L., (1990) Acta Chim. Sin., 48, p. 372
  • Einhorn, C., Luche, J.-L., (1987) J. Organomet. Chem., 322, p. 177
  • Pereyre, M., Quintard, J.-P., Rahm, A., (1987) Tin in Organic Synthesis, , See:, Butterworth, London
  • Smith, P.J., (1978) Toxicological Data on Organotin Compounds, , International Tin Research Inst., London
  • Chan, T.H., Li, C.-J., Wei, Z.Y., (1990) J. Chem. Soc., Chem. Commun., p. 505
  • Kim, E., Gordon, D.M., Schmid, W., Whitesides, G.M., (1993) J. Org. Chem., 58, p. 5500
  • Kundu, A., Prabhakar, S., Vairamani, M., Roy, S., (1997) Organometallics, 16, p. 4796
  • Kobayashi, Nishio, K., (1995) Tetrahedron Lett., 36, p. 6729. , Diallyltin dibromide has been found an efficient allylation reagent of carbonyl compounds in organic solvents. See:, and reference cited therein
  • Chan, T.H., Yang, Y., Li, C.-J., (1999) J. Org. Chem., 64, p. 4452
  • Bian, Y.-J., Xue, W.-L., Yu, X.-G., (2010) Ultrason. Sonochem., 17, p. 580
  • Lin, M.-H., Hung, S.-F., Lin, L.-Z., Tsai, W.-S., Chuang, T.-H., (2011) Org. Lett., 13, p. 332
  • Chan, T.H., Yang, Y., (1999) J. Am. Chem. Soc., 121, p. 3228
  • Chung, W.J., Higashiya, S., Oba, Y., Welch, J.T., (2003) Tetrahedron, 59, p. 10031
  • Podlech, J., Maier, T.C., (2003) Synthesis, p. 633
  • Paquette, L., (2003) Synthesis, p. 765
  • Shen, Z.-L., Cheong, H.-L., Loh, T.-P., (2009) Tetrahedron Lett., 50, p. 1051
  • Paquette, L., Mitzel, T.M., (1996) J. Am. Chem. Soc., 118, p. 1931
  • Araki, S., Jin, S.-J., Idou, Y., Butsugan, Y., (1992) Bull. Chem. Soc. Jpn., 65, p. 1736
  • Reetz, M.T., Jung, A., (1983) J. Am. Chem. Soc., 105, p. 4833
  • Narasaka, K., Pai, H.C., (1980) Chem. Lett., p. 1415
  • Narasaka, K., Pai, H.C., (1984) Tetrahedron, 12, p. 2233
  • Evans, D.A., Chapman, K.T., Carreira, E.M., (1988) J. Am. Chem. Soc., 110, p. 3560
  • Chen, X., Hortelano, E.R., Eliel, E.L., Frye, S.V., (1990) J. Am. Chem. Soc., 112, p. 6130
  • Chen, X., Hortelano, E.R., Eliel, E.L., Frye, S.V., (1992) J. Am. Chem. Soc., 114, p. 1778
  • Frye, S.V., Eliel, E.L., Cloux, R., (1987) J. Am. Chem. Soc., 109, p. 1862
  • Corcoran, R.C., Ma, J., (1992) J. Am. Chem. Soc., 114, p. 4536
  • Mori, S., Nakamura, M., Nakamura, E., Koga, N., Morukuma, K., (1995) J. Am. Chem. Soc., 117, p. 5055
  • Poll, T., Metter, J.O., Helmchen, G., (1985) Angew. Chem. Int. Ed. Engl., 24, p. 112
  • Buhro, W.E., Georgiou, S., Fernández, J.M., Patton, A.T., Strouse, C.E., Gladysz, J.A., (1986) Organometallics, 5, p. 956
  • Arai, M., Kawasuji, T., Nakamura, E., (1993) J. Org. Chem., 58, p. 5121
  • Petrier, C., Luche, J.-L., (1985) J. Org. Chem., 50, p. 910
  • Wilson, S.R., Guazzaroni, M.E., (1989) J. Org. Chem., 54, p. 3087
  • Chan, T.-H., Li S, C.-J., Lee, M.C., Wei, Z.Y., (1994) Can. J. Chem., 72, p. 1181
  • Smadja, W., (1994) Synlett, p. 1
  • Araki, S., Ito, H., Butsugan, Y., (1988) Synth. Commun., 18, p. 453
  • Marshall, J.A., (1995) J. Org. Chem., 60, p. 1920
  • Loh, T.-P., Hu, Q.-Y., Vittal, J.J., (2000) Synlett, p. 523
  • Lu, W., Ma, J., Yang, Y., Chan, T.H., (2000) Org. Lett., 2, p. 3469
  • Alcaide, B., Almendros, P., Rodriguez-Acebes, R., (2002) J. Org. Chem., 67, p. 1925
  • Yi, X.-H., Meng, Y., Li, C.-J., (1997) Tetrahedron Lett., 38, p. 4731
  • Usugi, S., Yorimitsu, H., Oshima, K., (2001) Tetrahedron Lett., 42, p. 4535
  • Chan, T.-H., Li, C.-J., (1990) Organometallics, 9, p. 2649
  • Araki, S., Kamei, T., Hirashita, T., Yamamura, H., Kawai, A., (2000) Org. Lett., 2, p. 847
  • Li, C.-J., Chan, T.H., (1999) Tetrahedron, 55, p. 11149
  • Lu, W., Chan, T.H., (2001) J. Org. Chem., 66, p. 3467
  • Miyabe, H., Yamaoka, Y., Naito, T., Takemoto, Y., (2003) J. Org. Chem., 68, p. 6745
  • Loh, T.-P., Tan, K.-T., Yang, J.-Y., Xiang, C.-L., (2001) Tetrahedron Lett., 42, p. 8701
  • Miyabe, H., Yamoaka, Y., Naito, T., Takemoto, Y., (2004) J. Org. Chem., 69, p. 1415
  • Estevam, I.H.S., Bieber, L.W., (2003) Tetrahedron Lett., 44, p. 667
  • Yi, X.-H., Meng, Y., Hua, X.-G., Li, C.-J., (1998) J. Org. Chem., 63, p. 7472
  • Alcaide, B., Almendros, P., Aragoncillo, C., Redondo, M.C., Torres, M.R., (2006) Chem. Eur. J., 12, p. 1539
  • Alcaide, B., Almendros, P., Aragoncillo, C., Redondo, M.C., (2007) J. Org. Chem., 72, p. 1604
  • Da Silva, A.D., Maria, E.J., Blanchard, P., Fourrey, J.-L., Robert-Gero, M., (1998) Nucleosides Nucleotides, 17, p. 2175
  • Maria, E.J., Da Silva, A.D., Fourrey, J.-L., (2000) Eur. J. Org. Chem., p. 627
  • Blanchard, P., Da Silva, A.D., El Kortbi, M.S., Fourrey, J.-L., Robert-Gero, M., (1993) J. Org. Chem., 58, p. 6517
  • Crich, D., Davies, J.W., Negrón, G., Quintero, L.J., (1988) Chem. Res. Synop., p. 140
  • Crich, D., Davies, J.W., (1989) Tetrahedron, 45, p. 5641
  • Yim, A.-M., Vidal, Y., Viallefont, P., Martinez, J., (1999) Tetrahedron Lett., 40, p. 4535
  • Shen, Z.-L., Yeo, Y.-L., Loh, T.-P., (2008) J. Org. Chem., 73, p. 3922
  • Gajewski, J.J., Bocian, W., Brichford, N.L., Henderson, J.L., (2002) J. Org. Chem., 67, p. 4236
  • Fleming, F.F., Gudipati, S., (2006) Org. Lett., 8, p. 1557
  • Kang, S., Jang, T.S., Keum, G., Kang, S.B., So-Yeop, H., Kim, Y., (2000) Org. Lett., 2, p. 3615
  • Mahesh, M., Murphy, J.A., Wessel, H.P., (2005) J. Org. Chem., 70, p. 4118
  • Fittig, R., (1859) Liebigs Ann., 110, p. 23
  • Nair, V., Deepthi, A., (2009) Tetrahedron, 65, p. 10745
  • Bhar, S., Guha, S., (2004) Tetrahedron Lett., 45, p. 3775
  • Li, L.H., Chan, T.H., (2000) Org. Lett., 2, p. 1129
  • Sahade, D.A., Mataka, S., Sawada, T., Tsukinoki, T., Tashiro, M., (1997) Tetrahedron Lett., 38, p. 3745
  • Khurana, J.M., Sehgal, A., (1994) J. Chem. Soc., Chem. Commun., p. 571
  • Ueda, T., Kanomata, N., Machida, H., (2005) Org. Lett., 7, p. 2365
  • Aspinall, H.C., Greeves, N., Valla, C., (2005) Org. Lett., 7, p. 1919
  • Matsukawa, S., Hinakubo, Y., (2003) Org. Lett., 5, p. 1221
  • Wang, L., Zhang, Y.M., (1998) Tetrahedron Lett., 39, p. 5257
  • Molander, G.A., Kenny, C., (1989) J. Am. Chem. Soc., 111, p. 8236
  • Namy, J.L., Souppe, J., Kagan, H.B., (1983) Tetrahedron Lett., 24, p. 765
  • Xu, X.L., Hirao, T., (2005) J. Org. Chem., 70, p. 8594
  • Hirao, T., Takeuchi, H., Ogawa, A., Sakurai, H., (2000) Synlett, p. 1658
  • Hirao, T., Hatano, B., Imamoto, Y., Ogawa, A., (1999) J. Org. Chem., 64, p. 7665
  • Kammermeier, B., Beck, G., Jendralla, H., Jacobi, D., (1994) Angew. Chem. Int. Ed. Engl., 33, p. 685
  • Annunziata, R., Benaglia, M., Cinquini, M., Cozzi, F., Giaroni, P., (1992) J. Org. Chem., 57, p. 782
  • Kempf, D.J., Sowin, T.J., Doherty, E.M., Hannick, S.M., Codavoci, L., Henry, R.F., Green, B.E., Norbeck, D.W., (1992) J. Org. Chem., 57, p. 5692
  • Freudenberger, J.H., Konradi, A.W., Pederson, S.F., (1989) J. Am. Chem. Soc., 111, p. 8014
  • Handy, S.T., Omune, D.A., (2005) Org. Lett., 7, p. 1553
  • Mukaiyama, T., Yoshimura, N., Igarashi, K., Kagayama, A., (2001) Tetrahedron, 57, p. 2499
  • Li, T.-Y., Cui, W., Liu, J.G., Zhao, J.Z., (2000) Chem. Commun., p. 139
  • Tsukinoki, T., Awaji, T., Hashimoto, I., Mataka, S., Tashiro, M., (1997) Chem. Lett., p. 235
  • Tanaka, K., Kishigami, S., Toda, F., (1990) J. Org. Chem., 55, p. 2981
  • Takai, K., Morita, R., Matsushita, H., Toratsu, C., (2003) Chirality, 15, p. 17
  • David, S.H., Gregory, C.F., (1995) J. Am. Chem. Soc., 117, p. 7283
  • Yamamoto, Y., Hattori, R., Itoh, K., (1999) Chem. Commun., p. 825
  • Groth, U., Jeske, M., (2001) Synlett, p. 129
  • Groth, U., Jeske, M., (2000) Angew. Chem. Int. Ed., 39, p. 574
  • Khan, R.H., Mathur, R.K., Ghosh, A.C., (1997) Synth. Commun., 27, p. 2193
  • Ephritikhine, M., Maury, O., Villiers, C., Lance, M., Nierlich, M., (1998) J. Chem. Soc., Dalton Trans., p. 3021
  • Svatos, A., Boland, W., (1998) Synlett, p. 126
  • Wang, Z.Y., Yuan, S.Z., Zha, Z.G., Zhang, Z.D., (2003) Chin. J. Chem., 21, p. 1231
  • Ohe, T., Ohse, T., Mori, K., Ohtaka, S., Uemura, S., (2003) Bull. Chem. Soc. Jpn., 76, p. 1823
  • Mori, K., Ohtaka, S., Uemura, S., (2001) Bull. Chem. Soc. Jpn., 74, p. 1497
  • Lim, H.J., Keum, G., Kang, S.B., Chung, B.Y., Kim, Y., (1998) Tetrahedron Lett., 39, p. 4367
  • Wang, C., Pan, Y., Wu, A., (2007) Tetrahedron, 63, p. 429
  • Chatterjee, A., Joshi, N.N., (2006) Tetrahedron, 62, p. 12137
  • Keller, C.L., Dalessandro, J.D., Hotz, R.P., Pinhas, A.R., (2008) J. Org. Chem., 73, p. 3616
  • Walling, C., (1998) Acc. Chem. Res., 31, p. 155
  • MacFaul, P.A., Wayner, D.D.M., Ingold, K.U., (1998) Acc. Chem. Res., 31, p. 159
  • Goldstein, S., Meyerstein, D., (1999) Acc. Chem. Res., 32, p. 547
  • Sawyer, D.T., Sobkowiak, A., Matsushita, T., (1996) Acc. Chem. Res., 29, p. 409
  • Hoffman, C.D.D., Jenner, E.L., Lipscomb, R.D., (1958) J. Am. Chem. Soc., 80, p. 2864
  • Walling, C., El-Taliawi, G.M., (1973) J. Am. Chem. Soc., 95, p. 844. , Also see:
  • Yang, Y.-S., Shen, Z.-L., Loh, T.-P., (2009) Org. Lett., 11, p. 2213
  • Tsukinoki, T., Nagashima, S., Mitoma, Y., Tashiro, M., (2000) Green Chem., 2, p. 117
  • Kalyanaman, N., Rao, V., (1993) Tetrahedron Lett., 34, p. 1647
  • Burchak, O.N., Py, S., (2009) Tetrahedron, 65, p. 7333
  • Nair, V., Ros, S., Jayan, C.N., Rath, N.P., (2002) Tetrahedron Lett., 43, p. 8967
  • Halterman, R.L., Porterfield, J.P., Mekala, S., (2009) Tetrahedron Lett., 50, p. 7172
  • Jiang, Y., Xi, C., Yang, X., (2005) Synlett, p. 1381
  • Xi, C., Jiang, Y., Yang, X., (2005) Tetrahedron Lett., 46, p. 3909
  • Postigo, A., Ferreri, C., Navacchia, M.L., Chatgilialoglu, C., (2005) Synlett, p. 2854
  • Postigo, A., (2009) Curr. Org. Chem., 13, p. 1683
  • Sayles, G.D., You, G., Wang, M., Kupferle, M., (1997) Environ. Sci. Technol., 31, p. 3448
  • Eykholt, G.R., Davenport, D.T., (1998) Environ. Sci. Technol., 32, p. 1482
  • Bridges, D.C., (1998) Triazine Herbicides: Risk Assessment, ACS Symposium Series 683, p. 24. , American Chemical Society, Washington, DC, L.G. Bal-lantine, J.E. McFarland, D. Hackett (Eds.)
  • Wackett, L., Atrazine Pathway Map, The University of Minnesota Biocatalysis/Biodegradation Database http://www.labmed.umn.edu/umbbd, Available online at:; Monson, S.J., Ma, L., Cassada, D.A., Spalding, R.F., (1998) Anal. Chim. Acta, 373, p. 153
  • Dombek, T., Dolan, E., Schultz, J., Klarup, D., (2001) Environ. Pollut., 111, p. 21
  • Weber, E.J., (1996) Environ. Sci. Technol., 30, p. 716
  • Hung, W.-H., Schwartz, J., Bernasek, S.L., (1991) Surf. Sci., 248, p. 332
  • Matheson, L.J., Tratnyek, P.G., (1994) Environ. Sci. Technol., 28, p. 2045
  • Johnson, T.L., Scherer, M.W., Tratnyek, P.G., (1996) Environ. Sci. Technol., 30, p. 2634
  • Tratnyek, P.G., Johnson, T.L., Scherer, M.M., Eykholt, G.R., (1997) Ground Water Monit. Rem., 17, p. 109
  • Tratnyek, P.G., Scherer, M., (1998) Proc. Natl. Conf. Environ. Eng., p. 110
  • Scherer, M.M., Balko, B.A., Gallagher, D.A., Tratnyek, P.G., (1998) Environ. Sci. Technol., 32, p. 3026
  • Johnson, T.L., William, F., Gorby, Y.A., Tratnyek, P.G., (1998) J. Contam. Hydrol., 29, p. 379
  • Ranu, B.C., Dutta, P., Sarkar, A., (1998) Tetrahedron Lett., 39, p. 9557
  • Ranu, B.C., Samanta, S., Das, A., (2002) Tetrahedron Lett., 43, p. 5993
  • Ranu, B.C., Dutta, J., Guchhait, S.K., (2001) Org. Lett., 3, p. 2603
  • Ranu, B.C., Chattopadhyay, K., Banerjee, S., (2006) J. Org. Chem., 71, p. 423
  • Ranu, B.C., Samanta, S., (2003) J. Org. Chem., 68, p. 7130
  • Ranu, B.C., Chattopadhyay, K., Adak, L., (2007) Org. Lett., 9, p. 4595
  • Alonnso, F., Beletskaya, I.P., Yus, M., (2002) Chem. Rev., 102, p. 4009. , For a review, see: S. Taciolu, Tetrahedron 52 (1996) 11113
  • Park, L., Keum, G., Kang, S.B., Kim, K.S., Kim, Y.J., (2000) Chem. Soc., Perkin Trans., 1, p. 4462
  • Chae, H., Sangwon, C., Keum, G., Kang, S.B., Pae, A.N., Kim, Y., (2000) Tetrahedron Lett., 41, p. 3899
  • Hirasawa, N., Takahashi, Y., Fukuda, E., Sugimoto, O., Tanji, K.-I., (2008) Tetrahedron Lett., 49, p. 1492
  • Kim, J.S., Jan, J.H., Lee, J.J., Jun, Y.M., Lee, B.M., Kim, B.H., (2008) Tetrahedron Lett., 49, p. 3733
  • Wang, C., Wan, J., Zheng, Z., Pan, Y., (2007) Tetrahedron, 63, p. 5071
  • Ankner, T., Hilmersson, G., (2007) Tetrahedron Lett., 48, p. 5707
  • Banik, B.K., Samajdar, S., Banik, I., (2003) Tetrahedron Lett., 44, p. 1699
  • Alcaide, B., Almendros, P., Aragoncillo, C., (2007) Chem. Rev., 107, p. 4437
  • Manabe, S., Ueki, A., Ito, Y., (2008) Tetrahedron Lett., 49, p. 5159
  • Zhang, Y., Wang, L., (1999) Tetrahedron, 55, p. 10695
  • Parmar, D., Duffy, L.A., Sadasivam, D.V., Matsubara, H., Bradly, P.A., Flowers, R.A., Procter, D.J., (2009) J. Am. Chem. Soc., 131, p. 15467
  • Guazelli, G., De Grazia, S., Collins, K.D., Matsubara, H., Spain, M., Procter, D.J., (2008) J. Am. Chem. Soc., 131, p. 7214
  • Dahlén, A., Hilmersson, G., (2005) J. Am. Chem. Soc., 127, p. 8340
  • Zeror, S., Collin, J., Fiaud, J.C., Zouioueche, L.A., (2006) J. Mol. Catal. A, 256, p. 85
  • Zeror, S., Collin, J., Fiaud, J.C., Zouioueche, L.A., (2010) Tetrahedron: Asymmetry, 21, p. 1211
  • Li, B.-Z., Che, J.-S., Dong, Z.-R., Li, Y.-Y., Li, Q.-B., Gao, J.-X., (2006) J. Mol. Catal. A, 258, p. 113
  • Micskei, C., Hadju, C., Wesshojann, L.U., Mercs, L., Kiss-Szikszai, A., Potonay, T., (2004) Tetrahedron: Asymmetry, 15, p. 1735
  • Chatgilialoglu, C., Newcomb, M., (1999) Adv. Organomet. Chem., 44, p. 67
  • Sasaki, S., Yamauchi, T., Kubo, H., Kanai, M., Ishii, A., Higashiyama, K., (2005) Tetrahedron Lett., 46, p. 1497. , See a recent review on Ce(III) reactions: G. Bartoli, E. Marcantoni, M. Marcolini, L. Sambri, Chem. Rev. 110 (2010) 6104
  • Tantawy, W., Zipse, H., (2007) Eur. J. Org. Chem., p. 5817
  • Pozzi, D., Renaud, P., (2007) Chimia, 61, p. 151
  • Spiegel, D.A., Wiberg, K.B., Schacherer, L.N., Madeiros, M.R., Wood, J.L., (2005) J. Am. Chem. Soc., 127, p. 12513
  • Cuerva, J.M., Campagna, A.C., Justicia, J., Rosales, A., Oller-Lòpez, J.L., Robles, R., Càrdenas, D.G., Oltra, E.J., (2006) Angew. Chem. Int. Ed., 45, p. 5522
  • Jin, J., Newcomb, M., (2007) J. Org. Chem., 72, p. 5098
  • Paradas, M., Campaña, A.G., Jimenez, T., Robles, R., Oltra, J.E., Buñuel, E., Justicia, J., Cuerva, J.M., (2010) J. Am. Chem. Soc., 132, p. 12748
  • Rabion, A., Buchanan, R.M., Seris, J.-L., Fish, R.H., (1997) J. Mol. Catal. A: Chem., 116, p. 43
  • Kirillova, M.V., Kirillov, A.M., Pombeiro, A.J.L., (2009) Adv. Synth. Catal., 351, p. 2936
  • Dhakshinamoorthy, A., Pitchumani, K., (2006) Tetrahedron, 62, p. 9911
  • Nam, W., Han, H.J., Oh, S.-Y., Lee, Y.J., Choi, M.-H., Han, S.-Y., Kim, C., Shin, W., (2000) J. Am. Chem. Soc., 122, p. 8677. , and references cited therein
  • Mansuy, D., Leclaire, J., Fontecave, M., Dansette, P., (1984) Tetrahedron, 40, p. 2847
  • Tuynman, A., Spelberg, J.L., Kooter, I.M., Schoemaker, H.E., Wever, R., (2000) J. Biol. Chem., 275, p. 3025
  • Matsushita, M., Kamata, K., Yamaguchi, K., Mizuno, N., (2005) J. Am. Chem. Soc., 127, p. 6632
  • Wallis, P.J., Booth, K.J., Patti, A.F., Scott, J.L., (2006) Green Chem., 8, p. 333

Citas:

---------- APA ----------
Postigo, A. & Nudelman, N.S. (2011) . Synthetically useful metal-mediated radical transformations in water and aqueous media. Coordination Chemistry Reviews, 255(23-24), 2991-3030.
http://dx.doi.org/10.1016/j.ccr.2011.07.015
---------- CHICAGO ----------
Postigo, A., Nudelman, N.S. "Synthetically useful metal-mediated radical transformations in water and aqueous media" . Coordination Chemistry Reviews 255, no. 23-24 (2011) : 2991-3030.
http://dx.doi.org/10.1016/j.ccr.2011.07.015
---------- MLA ----------
Postigo, A., Nudelman, N.S. "Synthetically useful metal-mediated radical transformations in water and aqueous media" . Coordination Chemistry Reviews, vol. 255, no. 23-24, 2011, pp. 2991-3030.
http://dx.doi.org/10.1016/j.ccr.2011.07.015
---------- VANCOUVER ----------
Postigo, A., Nudelman, N.S. Synthetically useful metal-mediated radical transformations in water and aqueous media. Coord. Chem. Rev. 2011;255(23-24):2991-3030.
http://dx.doi.org/10.1016/j.ccr.2011.07.015