Application of multipurpose dimethyl formamide-like task specific ionic liquid as a recyclable reagent for direct iodination of alcohols

الموضوعات : Iranian Journal of Catalysis

Ahmed Ali Hullio ¹ , G.M. Mastoi ²

1 - Dr. M.A Kazi Institute of Chemistry, University of Sindh Jamshoro-76080 Sindh, Pakistan.
2 - Dr. M.A Kazi Institute of Chemistry, University of Sindh Jamshoro-76080 Sindh, Pakistan.

تاريخ الإرسال : 05 الثلاثاء , ذو الحجة, 1432 تاريخ التأكيد : 05 الأربعاء , محرم, 1433 تاريخ الإصدار : 06 الخميس , محرم, 1433

الکلمات المفتاحية: DMF-like ionic liquid, Iminium chloride, Vilsmier reagent, Thioiminium salt, Alcohols and alkyl iodides,

ملخص المقالة :

A direct and an efficient conversion of a wide range of primary, secondary even tertiary alcohols to the corresponding iodides have been achieved under ionic liquid conditions. The method involves preparation of ionic liquid-based iminium chloride intermediate from DMF-like ionic liquid then stirring it with alcohol in present of sodium iodide. The higher yields of alkyl iodides were obtained within minimum time with simplest operational procedure. The DMF-like ionic liquids could be recycled.

المصادر:

[1] http://en.wikipedia.org/wiki/Dimethylformamide.
[2] J. Muzart, Tetrahedron, 65 (2009) 8313-8323.
[3] D. Samita, A.K. Panigrahi, G. C. Maikap, Tetrahedron Lett., 44 (2003) 1375-1377.
[4] S. Weike, W. Yiyi, J. Ling, Y. Yanyan, Z. Linyao, C. Zhiwei, L. Zhenhua, L. Jianjun, 42 (2010) 503–555.
[5] (5a) K. Venkataraman, D. R. Wagle, Tetrahedron Lett., 20 (1979) 3037–3040. (5b) G, Blotny, Tetrahedron, 62 (2006) 9507-9522.
[6] (a) D.C. Forbes, E.J. Barrett, D.L. Lewis, M.C. Smith, Tetrahedron Lett., 41 (2000) 9943-9947. (b) B.P. Bandgar, S.S. Pandit, Tetrahedron Lett., 43 (2002) 3413-3414. (c) D. Luca, L. Giacomelli, G. Taddei, M. J. Org. Chem., 66 (2001) 7907-7909. (d) G. Giacomelli, A. Porcheddu, M. Salaries, Org. Lett., 5 (2003) 2715-2517.
[7] L. De Luca, G. Giacomelli, A. Porcheddu, J. Org. Chem., 66 (2001) 7907-7909.
[8] C.O. Kangani, B.W. Day, Org. Lett., 10 (2008) 2645-2548.
[9] (a) L. De Luca, G. Giacomelli, A. Porcheddu, J. Org. Chem., 67 (2002) 6272-6274. (b) Y. Furuya, K. Ishihara, H. Yamamoto, J. Am. Chem. Soc., 127 (2005) 11240-11241. (c) C. Betti, D. Landini, M. AMaia, M. Pasi, SynLet., (2008) 908-910.
[10] L. De Luca, G. Giacomelli, A. Porcheddu, Org. Lett., 4 (2002) 553-555.
[11] L. De Luca, G. Giacomelli, A. Porcheddu, J. Org. Chem., 67 (2002) 6272-6274.[12] L. De Luca, G. Giacomelli, A. Porcheddu, J. Org. Chem., 67 (2002) 5152-5155.
[13] C.W. Chang, S.S Chang, C.S. Chao, K.T. Mong, Tetrahedron Lett., 50 (2009) 4536-45-42.
[14] A. A. Hullio, G.M Mastoi, K. M. Khan, Asian J. Chem, 23 (2011) 5411-5418.
[15] (a) D. Abhishek, A.K. Upadhyay, K. Pradeep, Tetrahedron lett., 51 (2010) 744. (b) K. Savita, K. Ajay, A. K. Gupta, Synth. Commun. 32 (2002) 2885-2891.
[16] S. Hartinger, In Science of Synthesis, Georg Thieme Verlag: New York, 35 (2007) 589− 672.
[17] B. R Castro, Org. React., 29 (1983) 1– 162.
[18] P J. Garegg, B. Samuelsson, J. Chem. Soc., Chem. Commun., 12, (1979) 978– 980.
[19] S.Hanessian, M.M. Ponpipom, P. Lavallee, Carbohydr. Res., 24 (1972) 45– 56.
[20] H. Loibner, E. Zbiral, Helv. Chim. Acta, 59 (1976) 2100– 2113.
[21] (a) S.R. Landauer, H.N. Rydon, J. Chem. Soc. 1953, 2224– 2234. (b) H. N. Rydon, Org. Synth. Coll., 6. 1988, 830– 832.
[22] M.E. Jung, P.L. Ornstein, Tetrahedron Lett., 18 (1977) 2659– 2662.
[23] (a) G.A. Olah, S. Narang, B.G.B. Gupta, R. Malhotra, J. Org. Chem. 44 (1979) 1247– 1251 (b) T. Morita, S. Yoshida, Y.Okamoto, H. Sakurai, Synthesis, 6 (1979) 379-384.
[24] J.F. Norris, Am. Chem. J. 38 (1907) 627– 642.
[25] W.W. Hartman, J.R. Byers, J.B. Dickey, Org. Synth. Coll. 2 (1943) 322-323.
[26] M. Lauwers, B. Regnier, V. Van Eenoo, J. N. Denis, A. Krief, Tetrahedron Lett., 20 (1979) 1801– 1804.
[27] M. Di Deo, E. Marcantoni, E. Torregiani, G. Bartoli, M. C. Bellucci, M. Bosco, L. Sambri, J. Org. Chem., 65 (2000) 2830– 2833.
[28] A. Kamal, G. Ramesh, N. Laxman, Synth. Commun., 31 (2001) 827– 833.
[29] H. Tajik, F. Shirini, M. A. Zolfigol, F. Samimi, Synth. Commun. 36 (2006) 91– 95.
[30] (a) H. Eilingsfeld, M. Seefelder, H. Weidinger, Angew. Chem. 72 (1960) 836– 845. (b) S. Hanessian, N. R. Plessas, Chem. Commun., (1967) 1152– 1155. (c) R. F. Dods, J. S. Roth, Tetrahedron Lett., 3 (1969) 165– 168. (d) D. R. Hepburn, H. R. Hudson, J. Chem. Soc., Perkin Trans. 1 (1976) 754– 757.
[31] R. Adam Ellwood, J. Porter Michael, J. Org. Chem., 74 (2009) 7982–7985.
[32] H. Firouzabadi, N. Iranpoor, M. Jafarpour, Tetrahedron Lett., 45 (2004) 7451–7454.
[33] A.A. Hullio, G.M. Mastoi, Chin. J. Chem., 1 (2012) (accepted).