Facts, Presumptions, And Myths On The Solvent-free And Catalyst-free Biginelli Reaction. What Is Catalysis For?

dc.creatorAlvim H.G.O.
dc.creatorLima T.B.
dc.creatorDe Oliveira A.L.
dc.creatorDe Oliveira H.C.B.
dc.creatorSilva F.M.
dc.creatorGozzo F.C.
dc.creatorSouza R.Y.
dc.creatorDa Silva W.A.
dc.creatorNeto B.A.D.
dc.date2014
dc.date2015-06-25T17:54:24Z
dc.date2015-11-26T14:33:18Z
dc.date2015-06-25T17:54:24Z
dc.date2015-11-26T14:33:18Z
dc.date.accessioned2018-03-28T21:36:42Z
dc.date.available2018-03-28T21:36:42Z
dc.identifier
dc.identifierJournal Of Organic Chemistry. American Chemical Society, v. 79, n. 8, p. 3383 - 3397, 2014.
dc.identifier223263
dc.identifier10.1021/jo5001498
dc.identifierhttp://www.scopus.com/inward/record.url?eid=2-s2.0-84898977244&partnerID=40&md5=ad49b6ea7ba6ccb738f2ca441eab0729
dc.identifierhttp://www.repositorio.unicamp.br/handle/REPOSIP/86675
dc.identifierhttp://repositorio.unicamp.br/jspui/handle/REPOSIP/86675
dc.identifier2-s2.0-84898977244
dc.identifier.urihttp://repositorioslatinoamericanos.uchile.cl/handle/2250/1247828
dc.descriptionThe current manuscript describes the role and importance of catalysis and solvent effects for the Biginelli multicomponent reaction. The overwhelming number of new catalysts and conditions recently published for the Biginelli synthesis, including in some manuscripts entitled catalyst-free and/or solvent-free have incentivized controversies and hot debates regarding the importance of developing new catalysts and reaction conditions to perform this very important multicomponent reaction. These so-called catalyst-free reports have generated much confusion in the field, requiring urgent elucidations. In this manuscript, we exemplify, demystify, and discuss the crucial role of catalysis, solvent effects, mechanisms, kinetics, facts, presumptions, and myths associated with the Biginelli reaction aiming to avoid current and future confusion and to stimulate new approaches. © 2014 American Chemical Society.
dc.description79
dc.description8
dc.description3383
dc.description3397
dc.descriptionDomling, A., Wang, W., Wang, K., (2012) Chem. Rev., 112, pp. 3083-3135
dc.descriptionCliment, M.J., Corma, A., Iborra, S., (2012) RSC Adv., 2, pp. 16-58
dc.descriptionToure, B.B., Hall, D.G., (2009) Chem. Rev., 109, pp. 4439-4486
dc.descriptionBonne, D., Constantieux, T., Coquerel, Y., Rodriguez, J., (2013) Chem. - Eur. J., 19, pp. 2218-2231
dc.descriptionIsambert, N., Duque, M.D.S., Plaquevent, J.C., Genisson, Y., Rodriguez, J., Constantieux, T., (2011) Chem. Soc. Rev., 40, pp. 1347-1357
dc.descriptionDe Graaff, C., Ruijter, E., Orru, R.V.A., (2012) Chem. Soc. Rev., 41, pp. 3969-4009
dc.descriptionBrauch, S., Van Berkel, S.S., Westermann, B., (2013) Chem. Soc. Rev., 42, pp. 4948-4962
dc.descriptionPanda, S.S., Khanna, P., Khanna, L., (2012) Curr. Org. Chem., 16, pp. 507-520
dc.descriptionGupta, A.K., Singh, N., Singh, K.N., (2013) Curr. Org. Chem., 17, pp. 474-490
dc.descriptionBiggs-Houck, J.E., Younai, A., Shaw, J.T., (2010) Curr. Opin. Chem. Biol., 14, pp. 371-382
dc.descriptionSimon, C., Constantieux, T., Rodriguez, J., (2004) Eur. J. Org. Chem., pp. 4957-4980
dc.descriptionGu, Y.L., (2012) Green Chem., 14, pp. 2091-2128
dc.descriptionSlobbe, P., Ruijter, E., Orru, R.V.A., (2012) Med. Chem. Commun., 3, pp. 1189-1218
dc.descriptionSingh, M.S., Chowdhury, S., (2012) RSC Adv., 2, pp. 4547-4592
dc.descriptionWegner, J., Ceylan, S., Kirschning, A., (2012) Adv. Synth. Catal., 354, pp. 17-57
dc.descriptionKappe, C.O., (2000) Eur. J. Med. Chem., 35, pp. 1043-1052
dc.descriptionKappe, C.O., (2000) Acc. Chem. Res., 33, pp. 879-888
dc.descriptionKappe, C.O., (1993) Tetrahedron, 49, pp. 6937-6963
dc.descriptionLacotte, P., Buisson, D.A., Ambroise, Y., (2013) Eur. J. Med. Chem., 62, pp. 722-727
dc.descriptionCrespo, A., El Maatougui, A., Biagini, P., Azuaje, J., Coelho, A., Brea, J., Loza, M.I., Sotelo, E., (2013) ACS Med. Chem. Lett., 4, pp. 1031-1036
dc.descriptionCanto, R.F.S., Bernardi, A., Battastini, A.M.O., Russowsky, D., Eifler-Lima, V.L., (2011) J. Braz. Chem. Soc., 22, pp. 1379-1388
dc.descriptionKaan, H.Y.K., Ulaganathan, V., Rath, O., Prokopcova, H., Dallinger, D., Kappe, C.O., Kozielski, F., (2010) J. Med. Chem., 53, pp. 5676-5683
dc.descriptionRovnyak, G.C., Kimball, S.D., Beyer, B., Cucinotta, G., Dimarco, J.D., Gougoutas, J., Hedberg, A., Moreland, S., (1995) J. Med. Chem., 38, pp. 119-129
dc.descriptionRovnyak, G.C., Atwal, K.S., Hedberg, A., Kimball, S.D., Moreland, S., Gougoutas, J.Z., Oreilly, B.C., Malley, M.F., (1992) J. Med. Chem., 35, pp. 3254-3263
dc.descriptionBiginelli, P., (1891) Gazz. Chim. Ital., 21, pp. 337-340
dc.descriptionBiginelli, P., (1891) Gazz. Chim. Ital., 21, pp. 455-461
dc.descriptionBiginelli, P., (1891) Ber. Dtsch. Chem. Ges., 24, pp. 1317-1319
dc.descriptionBiginelli, P., (1891) Ber. Dtsch. Chem. Ges., 24, pp. 2962-2967
dc.descriptionTron, G.C., Minassi, A., Appendino, G., (2011) Eur. J. Org. Chem., pp. 5541-5550
dc.descriptionBiginelli, P., (1893) Gazz. Chim. Ital., 23, pp. 360-416
dc.descriptionBiginelli, P., (1893) Ber. Dtsch. Chem. Ges., 26, p. 447
dc.descriptionDe Souza, R., Da Penha, E.T., Milagre, H.M.S., Garden, S.J., Esteves, P.M., Eberlin, M.N., Antunes, O.A.C., (2009) Chem. - Eur. J., 15, pp. 9799-9804
dc.descriptionSweet, F., Fissekis, J.D., (1973) J. Am. Chem. Soc., 95, pp. 8741-8749
dc.descriptionKappe, C.O., (1997) J. Org. Chem., 62, pp. 7201-7204
dc.descriptionFolkers, K., Johnson, T.B., (1933) J. Am. Chem. Soc., 55, pp. 3784-3791
dc.descriptionCepanec, I., Litvic, M., Filipan-Litvic, M., Grungold, I., (2007) Tetrahedron, 63, pp. 11822-11827
dc.descriptionAndrade, C.K.Z., Alves, L.M., (2005) Curr. Org. Chem., 9, pp. 195-218
dc.descriptionGawande, M.B., Bonifacio, V.D.B., Luque, R., Branco, P.S., Varma, R.S., (2013) Chem. Soc. Rev., 42, pp. 5522-5551
dc.descriptionJain, S.L., Singhal, S., Sain, B., (2007) Green Chem., 9, pp. 740-741
dc.descriptionChen, J., Spear, S.K., Huddleston, J.G., Rogers, R.D., (2005) Green Chem., 7, pp. 64-82
dc.descriptionTundo, P., Perosa, A., (2007) Chem. Soc. Rev., 36, pp. 532-550
dc.descriptionDewan, M., Kumar, A., Saxena, A., De, A., Mozumdar, S., (2012) PLoS One, 7. , e43078
dc.descriptionParaskar, A.S., Dewkar, G.K., Sudalai, A., (2003) Tetrahedron Lett., 44, pp. 3305-3308
dc.descriptionKhunt, R.C., Akbari, J.D., Manvar, A.T., Tala, S.D., Dhaduk, M.F., Joshi, H.S., Shah, A., (2008) Arkivoc, pp. 277-U278
dc.descriptionDadhania, A.N., Patel, V.K., Raval, D.K., (2011) J. Braz. Chem. Soc., 22, pp. 511-516
dc.descriptionDallinger, D., Kappe, C.O., (2007) Nat. Protoc., 2, pp. 317-321
dc.descriptionLiu, C.J., Wang, J.D., (2010) Molecules, 15, pp. 2087-2095
dc.descriptionSafari, J., Gandomi-Ravandi, S., (2014) RSC Adv., 4, pp. 11486-11492
dc.descriptionAlvim, H.G.O., De Lima, T.B., De Oliveira, H.C.B., Gozzo, F.C., De Macedo, J.L., Abdelnur, P.V., Silva, W.A., Neto, B.A.D., (2013) ACS Catal., 3, pp. 1420-1430
dc.descriptionRamos, L.M., Guido, B.C., Nobrega, C.C., Corrêa, J.R., Silva, R.G., De Oliveira, H.C.B., Gomes, A.F., Neto, B.A.D., (2013) Chem. - Eur. J., 19, pp. 4156-4168
dc.descriptionRamos, L.M., Tobio, A., Dos Santos, M.R., De Oliveira, H.C.B., Gomes, A.F., Gozzo, F.C., De Oliveira, A.L., Neto, B.A.D., (2012) J. Org. Chem., 77, pp. 10184-10193
dc.descriptionHallett, J.P., Welton, T., (2011) Chem. Rev., 111, pp. 3508-3576
dc.descriptionDupont, J., Scholten, J.D., (2010) Chem. Soc. Rev., 39, pp. 1780-1804
dc.descriptionSiedlecka, E.M., Czerwicka, M., Stolte, S., Stepnowski, P., (2011) Curr. Org. Chem., 15, pp. 1974-1991
dc.descriptionClark, J.H., Macquarrie, D.J., Sherwood, J., (2013) Chem. - Eur. J., 19, pp. 5174-5182
dc.descriptionBose, D.S., Fatima, L., Mereyala, H.B., (2003) J. Org. Chem., 68, pp. 587-590
dc.descriptionWang, R., Liu, Z.Q., (2012) J. Org. Chem., 77, pp. 3952-3958
dc.descriptionLu, J., Ma, H.R., (2000) Synlett, pp. 63-64
dc.descriptionAdibi, H., Samimi, H.A., Beygzadch, M., (2007) Catal. Commun., 8, pp. 2119-2124
dc.descriptionMartinez, S., Meseguer, M., Casas, L., Rodriguez, E., Molins, E., Moreno-Manas, M., Roig, A., Vallribera, A., (2003) Tetrahedron, 59, pp. 1553-1556
dc.descriptionCoelho, F., Eberlin, M.N., (2011) Angew. Chem., Int. Ed., 50, pp. 5261-5263
dc.descriptionEberlin, M.N., (2007) Eur. J. Mass Spectrom., 13, pp. 19-28
dc.descriptionCooks, R.G., Chen, H., Eberlin, M.N., Zheng, X., Tao, W.A., (2006) Chem. Rev., 106, pp. 188-211
dc.descriptionIfa, D.R., Wu, C.P., Ouyang, Z., Cooks, R.G., (2010) Analyst, 135, pp. 669-681
dc.descriptionSantos, L.S., (2011) J. Braz. Chem. Soc., 22, pp. 1827-1840
dc.descriptionSantos, L.S., (2008) Eur. J. Org. Chem., pp. 235-253
dc.descriptionVanberkel, G.J., McLuckey, S.A., Glish, G.L., (1992) Anal. Chem., 64, pp. 1586-1593
dc.descriptionBruins, A.P., (1991) Mass Spectrom. Rev., 10, pp. 53-77
dc.descriptionKolosov, M.A., Orlov, V.D., Beloborodov, D.A., Dotsenko, V.V., (2009) Mol. Divers., 13, pp. 5-25
dc.descriptionKolosov, M.A., Orlov, V.D., Vashchenko, V.V., Shishkina, S.V., Shishkinb, O.V., (2007) Collect. Czech. Chem. Commun., 72, pp. 1219-1228
dc.descriptionRanu, B.C., Hajra, A., Dey, S.S., (2002) Org. Process Res. Dev., 6, pp. 817-818
dc.descriptionArfan, A., Paquin, L., Bazureau, J.P., (2007) Russ. J. Org. Chem., 43, pp. 1058-1064
dc.descriptionHu, E.H., Sidler, D.R., Dolling, U.H., (1998) J. Org. Chem., 63, pp. 3454-3457
dc.descriptionMondal, J., Sen, T., Bhaumik, A., (2012) Dalton Trans., 41, pp. 6173-6181
dc.descriptionDa Silva, D.L., Fernandes, S.A., Sabino, A.A., De Fatima, A., (2011) Tetrahedron Lett., 52, pp. 6328-6330
dc.descriptionShi, X.-L., Yang, H., Tao, M., Zhang, W., (2013) RSC Adv., 3, pp. 3939-3945
dc.descriptionLi, P., Regati, S., Butcher, R.J., Arman, H.D., Chen, Z.X., Xiang, S.C., Chen, B.L., Zhao, C.G., (2011) Tetrahedron Lett., 52, pp. 6220-6222
dc.descriptionFu, N.Y., Yuan, Y.F., Cao, Z., Wang, S.W., Wang, J.T., Peppe, C., (2002) Tetrahedron, 58, pp. 4801-4807
dc.descriptionSalehi, P., Dabiri, M., Zolfigol, M.A., Fard, M.A.B., (2003) Tetrahedron Lett., 44, pp. 2889-2891
dc.descriptionKang, L.Q., Jin, D.Y., Cai, Y.Q., (2013) Synth. Commun., 43, pp. 1896-1901
dc.descriptionSafari, J., Zarnegar, Z., (2013) RSC Adv., 3, pp. 17962-17967
dc.descriptionSafaei Ghomi, J., Teymuri, R., Ziarati, A., (2013) Monatsh. Chem., 144, pp. 1865-1870
dc.descriptionKalita, H.R., Phukan, P., (2007) Catal. Commun., 8, pp. 179-182
dc.descriptionShobha, D., Chari, M.A., Mano, A., Selvan, S.T., Mukkanti, K., Vinu, A., (2009) Tetrahedron, 65, pp. 10608-10611
dc.descriptionLitvic, M., Vecenaj, I., Ladisic, Z.M., Lovric, M., Vinkovic, V., Filipan-Litvic, M., (2010) Tetrahedron, 66, pp. 3463-3471
dc.descriptionBao, S.S., Ma, L.F., Wang, Y., Fang, L., Zhu, C.J., Li, Y.Z., Zheng, L.M., (2007) Chem. - Eur. J., 13, pp. 2333-2343
dc.descriptionMurata, H., Ishitani, H., Iwamoto, M., (2010) Org. Biomol. Chem., 8, pp. 1202-1211
dc.descriptionYadav, J.S., Reddy, B.V.S., Sridhar, P., Reddy, J.S.S., Nagaiah, K., Lingaiah, N., Saiprasad, P.S., (2004) Eur. J. Org. Chem., pp. 552-557
dc.descriptionGholap, A.R., Venkatesan, K., Daniel, T., Lahoti, R.J., Srinivasan, K.V., (2004) Green Chem., 6, pp. 147-150
dc.descriptionWang, A.Q., Liu, X., Su, Z.X., Jing, H.W., (2014) Catal. Sci. Technol., 4, pp. 71-80
dc.descriptionRostamnia, S., Morsali, A., (2014) RSC Adv., 4, pp. 10514-10518
dc.descriptionNazari, S., Saadat, S., Fard, P.K., Gorjizadeh, M., Nezhad, E.R., Afshari, M., (2013) Monatsh. Chem., 144, pp. 1877-1882
dc.descriptionSafari, J., Gandomi-Ravandi, S., (2013) J. Mol. Catal. A: Chem., 373, pp. 72-77
dc.descriptionChen, W.Y., Qin, S.D., Jin, J.R., (2007) Catal. Commun., 8, pp. 123-126
dc.descriptionJoseph, J.K., Jain, S.L., Singhal, S., Sain, B., (2011) Ind. Eng. Chem. Res., 50, pp. 11463-11466
dc.descriptionTayebee, R., Amini, M.M., Ghadamgahi, M., Armaghan, M., (2013) J. Mol. Catal. A: Chem., 366, pp. 266-274
dc.descriptionPeng, J.J., Deng, Y.Q., (2001) Tetrahedron Lett., 42, pp. 5917-5919
dc.descriptionChen, X.F., Peng, Y.Q., (2008) Catal. Lett., 122, pp. 310-313
dc.descriptionSehout, I., Boulcina, R., Boumoud, B., Berree, F., Carboni, B., Debache, A., (2013) Lett. Org. Chem., 10, pp. 463-467
dc.descriptionLiberto, N.A., De Paiva Silva, S., De Fátima, Â., Fernandes, S.A., (2013) Tetrahedron, 69, pp. 8245-8249
dc.descriptionKarimi, B., Mobaraki, A., Mirzaei, H.M., Zareyee, D., Vali, H., (2014) ChemCatChem, 6, pp. 212-219
dc.descriptionPramanik, M., Bhaumik, A., (2014) ACS Appl. Mater. Interfaces, 6, pp. 933-941
dc.descriptionSafari, J., Zarnegar, Z., (2014) New J. Chem., 38, pp. 358-365
dc.descriptionVikse, K.L., Kwok, S., McDonald, R., Oliver, A.G., McIndoe, J.S., (2012) J. Organomet. Chem., 716, pp. 252-257
dc.descriptionHinderling, C., Adlhart, C., Chen, P., (1998) Angew. Chem., Int. Ed., 37, pp. 2685-2689
dc.descriptionAdlhart, C., Hinderling, C., Baumann, H., Chen, P., (2000) J. Am. Chem. Soc., 122, pp. 8204-8214
dc.descriptionLi, R.M., Smith, R.L., Kenttamaa, H.I., (1996) J. Am. Chem. Soc., 118, pp. 5056-5061
dc.descriptionChisholm, D.M., McIndoe, J.S., (2008) Dalton Trans., pp. 3933-3945
dc.descriptionAscher, U.M., Petzold, L.R., (1998) Computer Methods for Ordinary Differential Equations and Differential-Algebraic Equations, , SIAM: Society for Industrial and Applied Mathematics: Philadelphia
dc.descriptionPetzold, L.R., (1982), Sandia National Laboratory, Report no. SAND82-8637Bard, Y., (1974) Nonlinear Parameter Estimation, , Academic Press: London
dc.descriptionSchwaab, M., Silva, F.M., Queipo, C.A., Barreto Jr., A.G., Nele, M., Pinto, J.C., (2006) Chem. Eng. Sci., 61, pp. 5791-5806
dc.descriptionHeravi, M.M., Asadi, S., Lashkariani, B.M., (2013) Mol. Divers., 17, pp. 389-407
dc.descriptionHuang, Y.J., Yang, F.Y., Zhu, C.J., (2005) J. Am. Chem. Soc., 127, pp. 16386-16387
dc.descriptionFrisch, M.J., Trucks, G.W., Schlegel, H.B., Scuseria, G.E., Robb, M.A., Cheeseman, J.R., Scalmani, G., Fox, D.J., (2009) Gaussian 09, , Gaussian, Inc. Wallingford, CT
dc.descriptionYanai, T., Tew, D.P., Handy, N.C., (2004) Chem. Phys. Lett., 393, pp. 51-57
dc.descriptionStephens, P.J., Devlin, F.J., Chabalowski, C.F., Frisch, M.J., (1994) J. Phys. Chem., 98, pp. 11623-11627
dc.descriptionTawada, Y., Tsuneda, T., Yanagisawa, S., Yanai, T., Hirao, K., (2004) J. Chem. Phys., 120, pp. 8425-8433
dc.descriptionParr, R.G., Yang, W.T., (1984) J. Am. Chem. Soc., 106, pp. 4049-4050
dc.descriptionBreneman, C.M., Wiberg, K.B., (1990) J. Comput. Chem., 11, pp. 361-373
dc.descriptionXie, Z.-B., Wang, N., Wu, W.-X., Le, Z.-G., Yu, X.-Q., (2014) J. Biotechnol., 170, pp. 1-5
dc.languageen
dc.publisherAmerican Chemical Society
dc.relationJournal of Organic Chemistry
dc.rightsfechado
dc.sourceScopus
dc.titleFacts, Presumptions, And Myths On The Solvent-free And Catalyst-free Biginelli Reaction. What Is Catalysis For?
dc.typeArtículos de revistas


Este ítem pertenece a la siguiente institución