Biomass into chemicals: One-pot two- and three-step synthesis of quinoxalines from biomass-derived glycols and 1,2-dinitrobenzene derivatives using supported gold nanoparticles as catalysts. Climent, J, M., Corma, A., Herńandez, C, J., Hungría, B, A., Iborra, S., & Martínez-Silvestre, S. Journal of Catalysis, 292:118--129, Instituto de Tecnología Química (UPV-CSIC), Universitat Politècnica de Valencia, Consejo Superior de Investigaciones Científicas, Avenida de los Naranjos s/n, 46022 Valencia, Spain, 2012.
Biomass into chemicals: One-pot two- and three-step synthesis of quinoxalines from biomass-derived glycols and 1,2-dinitrobenzene derivatives using supported gold nanoparticles as catalysts [link]Paper  abstract   bibtex   
An efficient and selective one-pot two-step method, for the synthesis of quinoxalines by oxidative coupling of vicinal diols with 1,2-phenylenediamine derivatives, has been developed by using gold nanoparticles supported on nanoparticulated ceria (Au/CeO 2) or hydrotalcite (Au/HT) as catalysts and air as oxidant, in the absence of any homogeneous base. Reaction kinetics shows that the reaction controlling step is the oxidation of the diol to $α$-hydroxycarbonyl compound. Furthermore, a one-pot three-step synthesis of 2-methylquinoxaline starting from 1,2-dinitrobenzene and 1,2-propanediol has been successfully carried out with 98% conversion and 83% global yield to the final product. © 2012 Elsevier Ltd. All rights reserved.
@article{ Climent2012,
  abstract = {An efficient and selective one-pot two-step method, for the synthesis of quinoxalines by oxidative coupling of vicinal diols with 1,2-phenylenediamine derivatives, has been developed by using gold nanoparticles supported on nanoparticulated ceria (Au/CeO 2) or hydrotalcite (Au/HT) as catalysts and air as oxidant, in the absence of any homogeneous base. Reaction kinetics shows that the reaction controlling step is the oxidation of the diol to $α$-hydroxycarbonyl compound. Furthermore, a one-pot three-step synthesis of 2-methylquinoxaline starting from 1,2-dinitrobenzene and 1,2-propanediol has been successfully carried out with 98% conversion and 83% global yield to the final product. © 2012 Elsevier Ltd. All rights reserved.},
  address = {Instituto de Tecnología Química (UPV-CSIC), Universitat Politècnica de Valencia, Consejo Superior de Investigaciones Científicas, Avenida de los Naranjos s/n, 46022 Valencia, Spain},
  annote = {Cited By (since 1996): 1

        
Export Date: 15 January 2013

        
Source: Scopus

        
CODEN: JCTLA

        
doi: 10.1016/j.jcat.2012.05.002

        
Language of Original Document: English

        
Correspondence Address: Corma, A.; Instituto de Tecnología Química (UPV-CSIC), Universitat Politècnica de Valencia, Consejo Superior de Investigaciones Científicas, Avenida de los Naranjos s/n, 46022 Valencia, Spain; email: acorma@itq.upv.es

        
References: Corma, A., Iborra, S., Velty, A., (2007) Chem. Rev., 107, p. 2411; 
Huber, G.W., Iborra, S., Corma, A., (2006) Chem. Rev., 106, p. 4044; 
Gallezot, P., (2007) Green Chem., 9, p. 295; 
Christensen, C.H., Rass-Hansen, J., Marsden, C.C., Taarning, E., Egeblad, K., (2008) Chem. Sus. Chem., 1, p. 283; 
Van Haveren, J., Scott, E.L., Sanders, J., (2008) Biofuels Bioprod. Bioref., 2, p. 41; 
Roper, H., (2002) Starch-Starke, 54, p. 89; 
Lichtenthaler, F.W., (2002) Chem. Res., 35, p. 728; 
Lichtenthaler, F.W., Peters, S.C.R., (2004) Chimie, 7, p. 65; 
Lichtenthaler, F.W., (1998) Carbohydr. Res., 113, p. 69; 
Climent, M.J., Corma, A., De Frutos, P., Iborra, S., Noy, M., Velty, A., Concepcí{o}n, P., (2010) J. Catal., 269, p. 140; 
Rapp, K.M., Daub, J., Rapp, K.M., Daub, J., (1993) Nachwachsende Rohstoffe: Perspektiven für Die Chemie, p. 183. , Hrsg S. Warwel, G. Wulff, VCH Weinheim; 
Lehr, V., Sarlea, M., Ott, L., Vogel, H., (2007) Catal. Today, 121, p. 121; 
Pagliaro, M., Ciriminna, R., Kimura, H., Rossi, M., Pina, C.D., (2007) Angew. Chem. Int. Ed., 46, p. 4434; 
Zhou, C.H.C., Beltramini, J.N., Fan, Y.X., Lu, G.Q.M., (2008) Chem. Soc. Rev., 37, p. 527; 
Hazeldine, S.T., Polin, L., Kushner, J., Paluch, J., White, K., Edelstein, M., Palomino, E., Horwitz, J.P., (2001) J. Med. Chem., 44, p. 1758; 
Rong, F., Chow, S., Yan, S., Larson, G., Hong, Z., Wu, J., (2007) Bioorg. Med. Chem. Lett., 17, p. 1663; 
Jaso, A., Zarranz, B., Aldana, I., Monge, A., (2005) J. Med. Chem., 48, p. 2019; 
Smits, R.A., Lim, H.D., Hanzer, A., Zuidelverd, O.P., Guaita, E., Adami, M., Coruzzi, G., De Esch, I.J.P., (2008) J. Med. Chem., 51, p. 2457; 
Cheeseman, G.W.H., Werstiuk, E.S.G., (1978) Adv. Heterocycl. Chem., 22, p. 367; 
Yb, K., Yh, K., Jy, P., Sk, K., (2004) Bioorg. Med. Chem. Lett., 14, p. 541; 
Hui, X., Desrivot, J., Bories, C., Loiseau, P.M., Franck, X., Hocquemiller, R., Fidadere, B., (2006) Bioorg. Med. Chem. Lett., 16, p. 815; 
Sakata, G., Makino, K., Karasawa, Y., (1988) Heterocycles, 27, p. 2481; 
Brock, E.D., Lewis, D.M., Yousaf, T.I., Harper, H.H., (1999) The Procter and Gamble Company, USA, pp. WO9951688; 
Sessler, J.L., Maeda, H., Mizuno, T., Lynch, V.M., Furuta, H.J., (2002) Am. Chem. Soc., 124, p. 13474; 
Thomas, K.R.J., Velusamy, M., Lin, J.T., Chuen, C.-H., Tao, Y.-T., (2005) Chem. Mater., 17, p. 1860; 
Dailey, S., Feast, W.J., Peace, R.J., Sage, I.C., Till, S., Wood, E.L., (2001) J. Mater. Chem., 11, p. 2238; 
Crossley, M.J., Johnston, L.A., (2002) Chem. Commun., p. 1122; 
Sascha, O., Rudiger, F., (2004) Synlett, p. 1509; 
Brown, D.J., Quinoxalines supplements II (2004) The Chemistry of Heterocyclic Compounds, , E.C. Taylor, P. Wipf, John Wiley \& Sons New Jersey; 
Bhosale, R.S., Sarda, S.R., Andhapure, S.S., Jadhav, W.N., Bhusare, S.R., Pawar, R.P., (2005) Tetrahedron Lett., 46, p. 7183; 
Zhao, Z., Wisnoski, D.D., Wolkenberg, S.E., Leister, W.H., Wang, Y., Lindsley, C.W., (2004) Tetrahedron Lett., 45, p. 4873; 
More, S.V., Sastry, M.N.V., Yao, C.F., (2006) Green Chem., 8, p. 91; 
Srinivas, C., Kumar, C.N.S.S.P., Rao, V.J., Palaniappan, S., (2007) J. Mol. Catal. A: Chem., 256, p. 227; 
Aparicio, D., Attanasi, O.A., Filippone, P., Ignacio, R., Lillini, S., Mantellini, F., Palacios, F., De Los Santos, J.M., (2006) J. Org. Chem., 71, p. 5897; 
Raw, S.A., Wilfred, C.D., Taylor, R.J.K., (2004) Org. Biomol. Chem., 2, p. 788; 
Kim, S.Y., Park, K.H., Chung, Y.K., (2005) Chem. Commun., p. 1321; 
Robinson, R.S., Taylor, R.J.K., (2005) Synlett, p. 1003; 
Sithambaram, S., Ding, Y., Li, W., Shen, X., Gaenzler, F., Suib, S.L., (2008) Green Chem., 10, p. 1029; 
Singh, S.K., Gupta, P., Duggineni, S., Kundu, B., (2003) Synlett, 14, p. 2147; 
Antoniotti, S., Duñach, E., (2002) Tetrahedron Lett., 43, p. 3971; 
Cho, C.S., Oh, S.G., (2006) Tetrahedron Lett., 47, p. 5633; 
Corma, A., (2004) Catal. Rev., 46, p. 369; 
Climent, M.J., Corma, A., Iborra, S., (2009) Chem. Sus. Chem., 2, p. 500; 
Climent, M.J., Corma, A., Iborra, S., (2011) Chem. Rev., 111, p. 1072; 
Climent, M.J., Corma, A., Iborra, S., (2012) RSC Adv., 2, p. 16; 
Venu Gopal, D., Subrahmanyam, M., (2001) Catal. Commun., 2, p. 219; 
Rao, K.V., Subba, M., Subrahmanyam, M., (2002) Chem. Lett., 2, p. 234; 
Mallat, T., Baiker, A., (1994) Catal. Today, 19, p. 247; 
Murahashi, S.-I., Komiya, N., Murahashi, S.-I., (2004) Ruthenium in Organic Synthesis, p. 53. , Wiley-VCH Weinheim; 
Abad, A., Concepcion, P., Corma, A., Garcia, H., (2005) Angew. Chem. Int. Ed., 44, p. 4066; 
Abad, A., Almela, C., Corma, A., Garcia, H., (2006) Chem. Commun., 30, p. 3178; 
Jú{a}rez, R., Corma, A., Garcia, H., (2009) Green Chem., 11, p. 949; 
Cavani, F., Trifiŕ{o}, A., Vaccari, A., (1991) Catal. Today, 11, p. 173; 
Climent, M.J., Corma, A., Iborra, S., Santos, L., (2009) Chem. Eur. J., 15, p. 8834; 
Jacob, R.G., Dutra, L.G., Radatz, C.S., Mendes, S.R., Perin, G., Lenardao, E.J., (2009) Tetrahedron Lett., 50, p. 1495; 
Van Hardeveld, R., Hartog, F., (1969) Surf. Sci., 15, p. 189; 
Benfield, R.E., (1992) J. Chem. Soc. Faraday Trans., 88, p. 1107; 
Corma, A., García, H., (2008) Nanoparticles Catal., p. 389; 
Zhang, L., Kozmin, S.A., (2004) J. Am. Chem. Soc., 126, p. 11806; 
Fu, Q., Saltsburg, H., Flytzani-Stephanopoulos, M., (2003) Science, 301, p. 935; 
Guzman, J., Carrettin, S., Corma, A., (2005) J. Am. Chem. Soc., 127, p. 3286; 
Guzman, J., Carrettin, S., Fierro-Gonź{a}lez, J.C., Hao, L., Gates, B.C., Corma, A., (2005) Ang. Chem. Int. Ed., 44, p. 4778; 
Mitsudome, T., Noujima, A., Mizugaki, T., Jitsukawa, K., Kaneda, K., (2009) Green Chem., 11, p. 793; 
Mitsudome, T., Mikami, Y., Funai, H., Mizugaki, T., Jitsukawa, K., Kaneda, K., (2008) Angew. Chem. Int. Ed., 47, p. 138; 
Mitsudome, T., Mikami, Y., Ebata, K., Mizugaki, T., Jitsukawa, K., Kaneda, K., (2008) Chem. Commun., p. 4804; 
Ebitani, K., Motokura, K., Mizugak, T., Kaneda, K., (2005) Angew. Chem. Int. Ed., 44, p. 3423; 
Rey, F., Fornés, V., (1992) J. Chem. Soc. Faraday Trans., 88, p. 2223; 
Nielsen, I.S., Taarning, E., Egeblad, K., Madsen, R., Christensen, C.H., (2007) Catal. Lett., 116, p. 35; 
Azizi, Y., Petit, C., Pitchon, V., (2008) J. Catal., 256, p. 338; 
Corma, A., Gonź{a}lez-Arellano, C., Iglesias, M., Ś{a}nchez, F., (2009) Appl. Catal. A: Gen., 356, p. 99; 
Corma, A., Serna, P., (2006) Science, 313, p. 332},
  author = {Climent, M J and Corma, A and Herń{a}ndez, J C and Hungría, A B and Iborra, S and Martínez-Silvestre, S},
  issn = {00219517 (ISSN)},
  journal = {Journal of Catalysis},
  keywords = {1,2-Phenylenediamine,2-Methylquinoxaline,Au/CeO                          2 ,Au/HT,Biomass,Cascade process,Catalysts,Cerium compounds,Diol,Glycols,Heterogeneous catalyst,Metal nanoparticles,Quinoxaline,Quinoxalines,Reaction kinetics},
  pages = {118--129},
  title = {{Biomass into chemicals: One-pot two- and three-step synthesis of quinoxalines from biomass-derived glycols and 1,2-dinitrobenzene derivatives using supported gold nanoparticles as catalysts}},
  url = {https://www.scopus.com/inward/record.url?eid=2-s2.0-84863724897\&partnerID=40\&md5=cd7aca662d2bd4a0f98a285ac2bd67c6},
  volume = {292},
  year = {2012}
}

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