Solvent-free direct ortho C-acylation of phenolic systems by methanesulfonic acid as catalyst
Subject Areas : Iranian Journal of CatalysisHossein Naeimi 1 , Abdol Hamid Raesi 2 , Mohsen Moradian 3
1 - Department of Organic Chemistry, Faculty of Chemistry, University of Kashan, Kashan, 87317, I.R.Iran.
2 - Department of Organic Chemistry, Faculty of Chemistry, University of Kashan, Kashan, 87317, I.R.Iran.
3 - Department of Organic Chemistry, Faculty of Chemistry, University of Kashan, Kashan, 87317, I.R.Iran.
Keywords:
Abstract :
[1] C. Giuseppe, C, Giovanni, P. Andrea, S. Giovanni, U. Rocco, Pure Appl. Chem. 55 (1983) 1677-1688.
[2] G.A. Olah, Friedel–Crafts and Related Reactions, Ed, Wiley-Interscience: New York, 1964. Vol. 3, part 1, p 1253-1291.
[3] D.J. Crouse, S.L. Hurlbut, D.M.S. Wheeler, J. Org. Chem. 46 (1981) 374-378.
[4] T. Mukaiyama, T. Ohno, T. Nishimura, S. Han, S. Kobayashi, Chem. Lett. (1991) 1059-1062.
[5] A. Kawada, S. Mitamura, S. Kobayashi, Synlett. (1994) 545-546.
[6] A. Kawada, S. Mitamura, S. Kobayashi, J. Chem. Soc., Chem. Commun. (1996) 183-184.
[7] H. Kusama, K. Narasaka, Bull. Chem. Soc. Jpn. 68 (1995) 2379-2383.
[8] M. Kodomari, Y. Suzuki, K. Yoshida, Chem. Commun. (1997) 1567-1568.
[9] D.E. Pearson, C.A. Buehlr, Synthesis (1972) 533-542.
[10] F. Effenberger, D. Steegmuller, V. Null, T. Ziegler, Chem. Ber. 121 (1988) 125-130.
[11] A. Cornelis, P. Laszlo, S. Wang, Tetrahedron Lett. 34 (1993) 3849-3852.
[12] J.H. Clark, S.R. Culle, S.J. Barlow, T.W. Bastock, J. Chem. Soc., Perkin Trans 2, 6 (1994) 1117-1130.
[13] J. Dubac, M. Labrouillere, A. Laporterie, J.R. Desmurs Eur. Pat. Appl. EP: 698593 (Chem. Abstr. 316758y, (1996) 124).
[14] S. Pivsa-Art, K. Okuro, M. Miura, S. Murata, M. Nomura, J. Chem. Soc., Perkin Trans1, (1994) 1703-1707.
[15] G.A. Olah, Angew. Chem. Int. Ed. Engl. 32 (1993) 767-788.
[16] M. Yato, T. Ohwada, K. Shudo., J. Am. Chem. Soc., 113 (1991) 691-691.
[17] Y. Sato, M. Yato, T. Ohwada, S. Saito, K. Shudo, J. Am. Chem. Soc., 117, (1995) 3037-3043.
[18] F. Effenberger, G. Epple, Angew. Chem., Int. Ed. Engl., 11 (1972) 300-301.
[19] F. Effenberger, J.K. Eberhard, A.H. Maier, J. Am. Chem. Soc., 118 (1996) 12572-12579.
[20] G. Sartori, R. Maggi, Chem. Rev. 106 (2006) 1077-1104.
[21] B. Chiche, A. Finiels, C. Gauthier, P. Geneste, J. Org. Chem. 51 (1986) 2128-2130.
[22] C. Gauthier, B. Chiche, A. Finiels, P. Geneste, J. Mol. Catal. A: Chem., 50 (1989) 219-229.
[23] Q.L. Wang, Y. Ma, X. Ji, H. Yan, Q. Qiu, J. Chem. Soc., Chem. Commun. (1995) 2307-2308.
[24] A.P. Singh, A.K. Pandey, J. Mol. Catal. A: Chem., 123 (1997) 141-147.
[25] J. Kaur, I.V. Kozhevnikov, Chem. Commun. (2002) 2508-2509.
[26] B. Chiche, A. Finiels, C. Gautheir, P. Geneste, J. Mol. Catal., A: Chem., 42 (1987) 229-235.
[27] S.Kobayashi, M. Moriwaki, I. Hachiya, Tetrahedron Lett., 37 (1996) 4183-4186.
[28] M.H. Sarvari, H. Sharghi, Helv. Chim. Acta, 88 (2005) 2282-2287.
[29] L.F. Fieser, E.B. Hershberg, J. Am. Chem. Soc., 62 (1940) 49-53.
[30] D.O. Jang, J.G. Kim, Bull. Korean Chem. Soc., 30 (2009) 1435-1441.
[31] S.S. Kim, S.T. Kadam, H. Lee, Bull. Korean Chem. Soc., 30 (2009) 1071-1076.
[32] J. Koo, J. Org. Chem., 28 (1963) 1134-1135.
[33] W. Baker, G.E. Coates, F. Glockling, J. Chem. Soc., (1951) 1376-1377.
[34] H. Sharghi, B. Kaboudin, J. Chem. Res (S), 10 (1998) 628-629.
[35] H. Sharghi, M.H. Sarvari, R. Eskandari, Synthesis, 12 (2006) 2047-2052.
[36] P. Janney, M.D. Gernon, M. Wu, T. Buszta, Green Chem. 3 (1999) 127-140.
[37] H. Naeimi, L. Moradi, Russ. J. Org. Chem., 43 (2007) 1757-1759.
[38] H. Naeimi, L. Moradi, Catal. Commun., 7 (2006) 1067-1071.
[39] H. Naeimi, L. Moradi, J. Mol. Catal., A: Chem., 256 (2006) 242-246.