Acetylation of alcohol, phenols, thiols and amine promoted by succinimidinium hydrogensulfate ([H-Suc]HSO4) in the absence of solvent

Subject Areas : Iranian Journal of Catalysis

Farhad Shirini ¹ ( Department of Chemistry, College of Science, University of Guilan, Rasht, zip code 41335, I.R. Iran. )
Omid Goli-Jolodar ² ( Department of Chemistry, College of Science, University of Guilan, Rasht, zip code 41335, I.R. Iran. )
Mohadeseh Seddighi ³ ( Department of Chemistry, College of Science, University of Guilan, Rasht, zip code 41335, I.R. Iran. )

Received: 2015-08-01 Accepted : 2015-12-10 Published : 2016-06-01

Keywords:

References:

[1] V.I. Parvulescu, C. Hardacre, Chem. Rev. 107 (2007) 2615-2665.
[2] F.J. Hernandez-Fernandez, A.P. delos Rios, L.J. Lozano-Blanco, C. Godinez, J. Chem. Technol. Biotechnol. 85 (2010) 1423-1435.
[3] Y.W. Zhao, J.X. Long, F.G. Deng, X.F. Liu, Z. Li, C.G. Xia, J.J. Peng, Catal. Commun. 10 (2009)732-736.
[4] M.H. Han, W.L. Yi, Q. Wu, Y. Liu, Y.C. Hong, D.Z. Wang, Bioresour. Technol. 100 (2009) 2308-2310.
[5] X.H. Yuan, M. Chen, Q.X. Dai, X.N. Cheng, Chem. Eng. J. 146 (2009) 266-269.
[6] D. Jiang, Y.Y. Wang, M. Tu, L.Y. Dai, Chin. Chem. Lett. 19 (2008) 889-892.
[7] P. Elavarasan, K. Kondamudi, S. Upadhyayula, Chem. Eng. J. 166 (2011) 340-347.
[8] J.H. Shen, H. Wang, H.C. Liu, Y. Sun, A.M. Liu, J. Mol. Catal. A: Chem. 280 (2008) 24-28.
[9] A.L. Lapidus, O.L. Eliseev, Solid Fuel Chem. 44 (2010) 197-202.
[10] D. Fang, Q.R. Shi, J. Cheng, K. Gong, Z.L. Liu, Appl. Catal. A 345 (2008) 158-163.
[11] Q.W. Yang, Z.J. Wei, H.B. Xing, Q.L. Ren, Catal. Commun. 9 (2008) 1307-1311.
[12] J. Otera, Esterification: Methods, Reactions and Applications, 1st ed., Wiley–VCH, 2003. b) T.W. Greene, P.G.M. Wutz, Protective Groups in Organic Synthesis, 3rd Ed., Wiley, New York, 1999.
[13] X.L. Sun, T. Kai, H. Takayanagi, K. Furuhata, Synlett 9 (1999) 1399-1341.
[14] J.S. Yadav, A.V. Narsaiah, A.K. Basak, P.R. Goud, D. Sreenu, K. Nagaiah, J. Mol. Catal. A Chem. 255 (2006) 78-80.
[15] a) E.F.V. Scriven, Chem. Soc. Rev. 12 (1983) 129-161. b) G. Höfle, V. Steglich, H. Vorbrüggen, Angew. Chem. Int. Ed. Engl. 17 (1978) 569-583.
[16] T. Sano, K. Ohashi, T. Oriyama, Synthesis (1999) 1141-1144.
[17] E. Vedejs, N.S. Bennett, L.M. Conn, S.T. Diver, M. Gingras, S. Lin, P.A. Oliver, M.J. Peterson, J. Org. Chem. 58 (1993) 7286-7288. b) E. Vedjes, T.S. Diver, J. Am. Chem. Soc. 115 (1993) 3358-3359.
[18] a) R. Borah, N. Deka, J. Sarma, J. Chem. Res. (S). (1997) 110-111. b) P. Phukan, Tetrahedron Lett. 45 (2004) 4785-4787.
[19] A.C. Cope, E.C. Herrich, Organic Synthesis Collective, Vol. IV, Wiley, New York, (1963) p. 304.
[20] S.S. Rana, J.J. Barlow, K.L. Matta, Tetrahedron Lett. 22 (1981) 5007-5010. b) G.W. Breton, M.J. Kurtz, S.L. Kurtz, Tetrahedron Lett. 38 (1997) 3825-3828.
[21] R.H. Baker, G. Bordwell, Organic Synthesis Collective, Vol. III, Wiley, New York, (1995) p. 141.
[22] J. Iqbal, R. Srivastava, J. Org. Chem. 57 (1992) 2001-2007.
[23] A.X. Li, T.S. Li, T.H. Ding, Chem. Commun. (1997) 1389. b) H. Hagiwara, K. Morohashi, T. Suzuki, M. Ando, I. Yamamoto, M. Kato, Synth. Commun. (1998) 2001-2006.
[24] R. Ballini, G. Bosica, S. Carloni, L. Ciaralli, R. Maggi, G. Sartori, Tetrahedron Lett. 39 (1998) 6049-6052.
[25] M. Curini, F. Epifano, M.C. Marcotullio, O. Rosati, M. Rossi, Synth. Commun. 30 (2000) 1319-1329.
[26] K. Ishihara, M. Kubota, H. Kurihara, H. Yamamoto, J. Org. Chem. 61 (1996) 4560-4567.
[27] S. Chandrasekhar, T. Ramachander, M. Takhi, Tetrahedron Lett. 39 (1998) 3263-3266.
[28] P.A. Procopiou, S.P.D. Baugh, S.S. Flack, G.G.A. Inglis, Chem. Commun. (1996) 2625-2626. b) P.A. Procopiou, S.P.D. Baugh, S.S. Flack, G.G.A. Inglis, J. Org. Chem. 63 (1998) 2342-2347.
[29] P. Saravanan, V.K. Singh, Tetrahedron Lett. 40 (1999) 2611-2614.
[30] K.K. Chauhan, C.G. Frost, I. Love, D. Waite, Synlett (1999) 1743-1744.
[31] S.V. Pansare, M.G. Malusare, A.N. Rai, Synth. Commun. 30 (2000) 2587-2592.
[32] I. Mohammadpoor-Baltork, H. Aliyan, A.R. Khosropour, Tetrahedron 57 (2001) 5851-5854.
[33] A. Parmar, J. Kaur, R. Goyal, B. Kumar, H. Kumar, Synth. Commun. 28 (1998) 2821-2826.
[34] K. De, Tetrahedron Lett. 45 (2004) 2919-2922.
[35] A.K. Chakraborti, R. Gulhane, Tetrahedron Lett. 44 (2003) 6749-6753.
[36] R. Dalpozzo, A.D. Nino, L. Maiuolo, A. Procopiou, M. Nardi, G. Bartoli, R. Romeo, Tetrahedron Lett. 44 (2003) 5621-5624.
[37] A. K. Chakraborti, L. Sharma, R. Gulhane, Shivani, Tetrahedron. 59 (2003) 7661-7668.
[38] A.K. Chakraborti, R. Gulhane, Synlett 4 (2004) 627-630.
[39] M.L. Kantam, K. Aziz, P.R. Likhar, Catal. Commun. 7 (2006) 484-487.
[40] V. Mirkhani, S. Tangestaninejad, M. Moghadam, B. Yadollahi, L. Alipanah, Monatsh. Chem. 135 (2004) 1257-1263.
[41] F. Shirini, O.G. Jolodar, M. Seddighi, H. Takbiri Borujeni, RSC Adv. 5 (2015) 19790-19798.
[42] A.R. Hajipour, L. Khazdooz, A.E. Ruohoa, J. Chin. Chem. Soc. 56 (2009) 398-403.