Samarium Iodide Research Paper

Samarium (II) Iodide

A single electron transfer reagent useful for organic synthesis.

A look into samarium (II) Iodide (Sml2), a powerful single electron donor which plays a vital role in the chemoselective reduction of certain functional groups and carbon-carbon bond formations.

Cathal McKenna Student Number: 11322441

10/6/2014

Introduction

Samarium (II) Iodide has emerged in recent times as a very useful reagent in organic synthesis. The compound was first used by Kagan and his researchers in 1977, who published a series of papers in 1980 regarding its uses as a single electron transfer reagent[1]. Since then it has been used widely for an array of reactions, for Carbon-Carbon bond formations such as the Barbier and radical-alkene/alkyne

Sml2 and Ybl2 are easy to prepare and to handle. Generally reactions using these reagents are clean. In addition, the lanthanide metals and salts are not known to be toxic and are easily available materials[1].” Samarium Iodide began to be seen as an invaluable reagent for any chemist due to its versatility, its large reduction potential (up to -2.05 in the presence of HMPA) and its tolerance to many functional groups[2]. It was this research that lead to SmI2 becoming used as a leading reducing agent in Organic

Nicolaou, K.C., S.P. Ellery, and J.S. Chen, Samarium Diiodide Mediated Reactions in Total Synthesis. Angewandte Chemie International Edition, 2009. 48(39): p. 7140-7165.

3. Gray, T., The Elements: A Visual Exploration of Every Known Atom in the Universe. , ed. N.Y.B.D.L. Publishers. 2009: York: Black Dog & Leventhal Publishers. .

4. D. J. Procter, R.A.F.I., T. Skrydstrup, Organic Synthesis using Samarium Diiodide: A Practical Guide. 2009, Cambridge: RSC Publishing.

5. Evans, W.J., T.S. Gummersheimer, and J.W. Ziller, Coordination Chemistry of Samarium Diiodide with Ethers Including the Crystal Structure of Tetrahydrofuran-Solvated Samarium Diiodide, SmI2(THF)5. Journal of the American Chemical Society, 1995. 117(35): p. 8999-9002.

6. Fukuzawa, S.-i., et al., Samarium(II) Triflate as a New Reagent for the Grignard-Type Carbonyl Addition Reaction. The Journal of Organic Chemistry, 1996. 61(16): p. 5400-5405.

7. Keck, G.E., Directed Reduction of β-Amino Ketones to Syn or Anti 1,3-Amino Alcohol Derivatives. Organic Letters, 2002. 4(18): p. 3131.

8. Kang, H.-Y. and S.-E. Song, Barbier-type reactions of nitriles and alkyl iodides mediated by samarium(II) iodide in the presence of catalytic nickel(II) iodide. Tetrahedron Letters, 2000. 41(6): p.