STUDY ON THE SYNTHESIS OF AMINOALCOHOL VIA REACTION BETWEEN ALDEHYDE AND IMINE BY SAMARIUM (II) IODIDE CATALYST
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Samarium (II) iodide; Aminoalcohol; Pinacol coupling; Imine.Abstract
Samarium (II) iodide (SmI2) has become one of the common, effective catalysts for coupling reactions between carbonyl compounds to form 1,2-diol by initiating free radical formation. In this paper, we present the results of studying the role of SmI2 catalyst on the aza-pinacol coupling reaction between aldehyde and imine under different mole ratios of SmI2, temperature and solvent conditions. The results showed that, in the THF solvent, at -78 °C, with 2.0 mole equivalent of the SmI2 catalyst, the reaction of pinacol coupling produces 1,2-aminoalcohols with efficiency of up to 91% yield and limited 1,2-diol by product.
References
[1]. Girard, P., Namy, J. L., & Kagan, H. B., “Divalent lanthanide derivatives in organic synthesis. Mild preparation of samarium iodide and ytterbium iodide and their use as reducing or coupling agents”, Journal of the American Chemical Society, 102(8) (1980), pp. 2693 - 2698.
[2]. Fuchs, J. R., Mitchell, M. L., Shabangi, M., & Flowers, R. A., “The effect of lithium bromide and lithium chloride on the reactivity of SmI2 in THF”, Tetrahedron Letters, 38(47) (1997), pp. 8157 - 8158.
[3]. Szostak, M., Spain, M., & Procter, D. J., “Recent advances in the chemoselective reduction of functional groups mediated by samarium(II) iodide: a single electron transfer approach”, Chemical Society Reviews, 42(23) (2013), pp. 9155 - 9183.
[4]. Masson, G., Py, S., & Vallée, Y., “Samarium Diiodide-Induced Reductive Cross-Coupling of Nitrones with Aldehydes and Ketones”, Angewandte Chemie International Edition, 41(10) (2002), pp. 1772 - 1775.
[5]. Molander, Gary A. "Reductions with Samarium(II) Iodide", Organic Reactions, (2004), pp. 211–367.
[6]. David J Procter, Robert A Flowers, Troels Skrydstrup, “Organic Synthesis Using Samarium Diiodide: A Practical Guide”, Royal Society Of Chemistry, Cambridge (2010), pp.69 - 144.
[7]. Szostak, M., Fazakerley, N. J., Parmar, D., & Procter, D. J., “Cross-Coupling Reactions Using Samarium(II) Iodide”, Chemical Reviews, 114(11) (2014), pp. 5959 - 6039.
