Co(porphyrin)-catalysed amination of 1,2-dihydronaphthalene derivatives by aryl azides. Zardi, P., Intrieri, D., Caselli, A., & Gallo, E. Journal of Organometallic Chemistry, 716:269-274, 2012. cited By 14
Co(porphyrin)-catalysed amination of 1,2-dihydronaphthalene derivatives by aryl azides [link]Paper  doi  abstract   bibtex   
Co(porphyrin) complexes promote an unusual reactivity of dihydronaphthalene towards several aryl azides. The reaction affords the benzylic amine of tetrahydronaphthalene instead yielding the amine of dihydronaphthalene as it normally happens in the presence of Ru(porphyrin)CO catalysts. The amination process occurs with the concomitant reduction of the dihydronaphthalene double bond probably due to the high reactivity of the endocyclic CC bond coupled with the good hydrogen donor capability of dihydronaphthalene. Two mechanisms for this reaction are proposed. © 2012 Elsevier B.V. All rights reserved.
@ARTICLE{Zardi2012269,
author={Zardi, P. and Intrieri, D. and Caselli, A. and Gallo, E.},
title={Co(porphyrin)-catalysed amination of 1,2-dihydronaphthalene derivatives by aryl azides},
journal={Journal of Organometallic Chemistry},
year={2012},
volume={716},
pages={269-274},
doi={10.1016/j.jorganchem.2012.07.013},
note={cited By 14},
url={https://www.scopus.com/inward/record.uri?eid=2-s2.0-84865002399&doi=10.1016%2fj.jorganchem.2012.07.013&partnerID=40&md5=32c1d6226eecb875ff9e4d895add9db9},
affiliation={Dipartimento di Chimica, Università degli Studi di Milano, Via Venezian 21, 20133 Milano, Italy},
abstract={Co(porphyrin) complexes promote an unusual reactivity of dihydronaphthalene towards several aryl azides. The reaction affords the benzylic amine of tetrahydronaphthalene instead yielding the amine of dihydronaphthalene as it normally happens in the presence of Ru(porphyrin)CO catalysts. The amination process occurs with the concomitant reduction of the dihydronaphthalene double bond probably due to the high reactivity of the endocyclic CC bond coupled with the good hydrogen donor capability of dihydronaphthalene. Two mechanisms for this reaction are proposed. © 2012 Elsevier B.V. All rights reserved.},
author_keywords={Amination reactions;  Cobalt;  Homogeneous catalysis;  Porphyrin},
keywords={Amination reaction;  Aryl azides;  Benzylic amines;  C-C bonds;  Co catalysts;  Concomitant reduction;  Double bonds;  High reactivity;  Homogeneous catalysis;  Hydrogen donor;  Tetrahydronaphthalenes, Amines;  Cobalt;  Hydrogen;  Naphthalene;  Reaction kinetics, Porphyrins},
references={Bräse, S., Banert, K., (2010) Organic Azides Syntheses and Applications, , John Wiley & Sons Ltd; Bräse, S., Gil, C., Knepper, K., Zimmermann, V., (2005) Angew. Chem. Int. Ed. Engl., 44, pp. 5188-5240; Cenini, S., Gallo, E., Caselli, A., Ragaini, F., Fantauzzi, S., Piangiolino, C., (2006) Coord. Chem. Rev., 250, pp. 1234-1253; Söderberg, B.C.G., (2000) Curr. Org. Chem., 4, pp. 727-764; Driver, T.G., (2010) Org. Biomol. Chem., 8, pp. 3831-3846; Cenini, S., Ragaini, F., Gallo, E., Caselli, A., (2011) Curr. Org. Chem., 15, pp. 1578-1592; Lu, H., Zhang, X.P., (2011) Chem. Soc. Rev., 40, pp. 1899-1909; Che, C.-M., Lo, V.K.-Y., Zhou, C.-Y., Huang, J.-S., (2011) Chem. Soc. Rev., 40, pp. 1950-1975; Fantauzzi, S., Caselli, A., Gallo, E., (2009) Dalton Trans., pp. 5434-5443; Liu, Y., Wei, J., Che, C.-M., (2010) Chem. Commun., 46, pp. 6926-6928; Liu, Y., Che, C.-M., (2010) Chem. Eur. J., 16, pp. 10494-10501; Intrieri, D., Caselli, A., Ragaini, F., MacChi, P., Casati, N., Gallo, E., (2011) Eur. J. Inorg. Chem., 2012, pp. 569-580; Intrieri, D., Caselli, A., Ragaini, F., Cenini, S., Gallo, E., (2010) J. Porphyrins Phthalocyanines, 14, pp. 732-740; Fantauzzi, S., Gallo, E., Caselli, A., Ragaini, F., Casati, N., MacChi, P., Cenini, S., (2009) Chem. Commun., pp. 3952-3954; Gallo, E., Buonomenna, M.G., Vigano, L., Ragaini, F., Caselli, A., Fantauzzi, S., Cenini, S., Drioli, E., (2008) J. Mol. Catal. A, 282, pp. 85-91; Fantauzzi, S., Gallo, E., Caselli, A., Piangiolino, C., Ragaini, F., Cenini, S., (2007) Eur. J. Org. Chem., pp. 6053-6059; Piangiolino, C., Gallo, E., Caselli, A., Fantauzzi, S., Ragaini, F., Cenini, S., (2007) Eur. J. Org. Chem., pp. 743-750; Caselli, A., Gallo, E., Ragaini, F., Ricatto, F., Abbiati, G., Cenini, S., (2006) Inorg. Chim. Acta, 359, pp. 2924-2932; Fantauzzi, S., Gallo, E., Caselli, A., Ragaini, F., MacChi, P., Casati, N., Cenini, S., (2005) Organometallics, 24, pp. 4710-4713; Lyaskovskyy, V., Suarez, A.I.O., Lu, H., Jiang, H., Zhang, X.P., De Bruin, B., (2011) J. Am. Chem. Soc., 133, pp. 12264-12273; Suarez, A.I.O., Jiang, H., Zhang, X.P., De Bruin, B., (2011) Dalton Trans., 40, pp. 5697-5705; Lu, H., Jiang, H., Hu, Y., Wojtas, L., Zhang, X.P., (2011) Chem. Sci., 2, pp. 2361-2366; Lu, H.-J., Subbarayan, V., Tao, J.-R., Zhang, X.P., (2010) Organometallics, 29, pp. 389-393; Lu, H., Tao, J., Jones, J.E., Wojtas, L., Zhang, X.P., (2010) Org. Lett., 12, pp. 1248-1251; Jones, J.E., Ruppel, J.V., Gao, G.-Y., Moore, T.M., Zhang, X.P., (2008) J. Org. Chem., 73, pp. 7260-7265; Caselli, A., Gallo, E., Fantauzzi, S., Morlacchi, S., Ragaini, F., Cenini, S., (2008) Eur. J. Inorg. Chem., pp. 3009-3019; Ruppel, J.V., Kamble, R.M., Zhang, X.P., (2007) Org. Lett., 9, pp. 4889-4892; Gao, G.-Y., Jones, J.E., Vyas, R., Harden, J.D., Zhang, X.P., (2006) J. Org. Chem., 71, pp. 6655-6658; Cenini, S., Gallo, E., Penoni, A., Ragaini, F., Tollari, S., (2000) Chem. Commun., pp. 2265-2266; Ragaini, F., Penoni, A., Gallo, E., Tollari, S., Gotti, C.L., Lapadula, M., Mangioni, E., Cenini, S., (2003) Chem. Eur. J., 9, pp. 249-259; Fantauzzi, S., Gallo, E., Caselli, A., Piangiolino, C., Ragaini, F., Re, N., Cenini, S., (2009) Chem. Eur. J., 15, pp. 1241-1251; Hopmann, K.H., Ghosh, A., (2011) ACS Catal., 1, pp. 597-600; Yamawaki, M., Tanaka, M., Abe, T., Anada, M., Hashimoto, S., (2007) Heterocycles, 72, pp. 709-721; Henery-Logan, K.R., Clark, R.A., (1968) Tetrahedron Lett., pp. 801-806; Anderson, G.T., Henry, J.R., Weinreb, S.M., (1991) J. Org. Chem., 56, pp. 6946-6948; Pajak, J., Brower, K.R., (1985) J. Org. Chem., 50, pp. 2210-2216; Franz, J.A., Camaioni, D.M., Beishline, R.R., Dalling, D.K., (1984) J. Org. Chem., 49, pp. 3563-3570; Pitchumani, K., Lakshminarasimhan, P.H., Turner, G., Bakker, M.G., Ramamurthy, V., (1997) Tetrahedron Lett., 38, pp. 371-374; Rosenfeld, A., Blum, J., Avnir, D., (1996) J. Catal., 164, pp. 363-368; Beishline, R.R., Gould, B., Walker, E.B., Stuart, D.K., Schultzski, J., Shigley, J.K., Calvert, K., Anderson, L.L., (1982) J. Org. Chem., 47, pp. 1668-1673; De Bruin, B., Dzik, W.I., Li, S., Wayland, B.B., (2009) Chem. Eur. J., 15, pp. 4312-4320; Jaz, J., De Hault, E.D., Navette, R., (1965) Tetrahedron Lett., 6, pp. 2751-2755; Tanno, M., Sueyoshi, S., Kamiya, S., (1982) Chem. Pharm. Bull., 30, pp. 3125-3132; Adler, A.D., Longo, F.R., Finarelli, J.D., Goldmacher, J., Assour, J., Korsakoff, L., (1967) J. Org. Chem., 32, p. 476; Lindsey, J.S., Schreiman, I.C., Hsu, H.C., Kearney, P.C., Marguerettaz, A.M., (1987) J. Org. Chem., 52, pp. 827-836; Adler, A.D., Longo, F.R., Váradi, V., Little, R.G., (2007) Inorganic Syntheses, pp. 213-220. , John Wiley & Sons, Inc; Bogdanowicz-Szwed, K., Krasodomska, M., (1994) Monatsh. Chem., 125, pp. 1247-1258; Wang, C., Pettman, A., Bacsa, J., Xiao, J., (2010) Angew. Chem. Int. Ed. Engl., 49, pp. 7548-7552; Yoshikai, N., Matsumoto, A., Norinder, J., Nakamura, E., (2009) Angew. Chem. Int. Ed. Engl., 48, pp. 2925-2928; Yang, Q., Shang, G., Gao, W., Deng, J., Zhang, X., (2006) Angew. Chem. Int. Ed. Engl., 45, pp. 3832-3835},
correspondence_address1={Gallo, E.; Dipartimento di Chimica, Via Venezian 21, 20133 Milano, Italy; email: emma.gallo@unimi.it},
issn={0022328X},
coden={JORCA},
language={English},
abbrev_source_title={J. Organomet. Chem.},
document_type={Article},
source={Scopus},
}

Downloads: 0