1. Mingli Li 2014-6-7 1

2. 2

3. ( stored as THF solutions, blue-green for SmI 2 and yellow-green for YbI 2 ) Deoxygenation Reactions Reductions of Double Bonds Reduction of Halides and Tosylates Alkylations of Ketones by Organic Halides or Organic Sulfonates. Girard, P.; Namy, J. L.; Kagan, H. B. J. Am. Chem. Soc. 1980, 102, 2693. SmI 2 3

4. 1 reductive manipulations of functional groups 2 reductive couplings to make C− C bonds 2.1 Barbier–Grignard processes ( the reaction of organic halides with carbonyl compounds ) 2.2 Radical alkene addition reactions 2.3 Ketyl radical alkene addition reactions 2.4 Pinacol coupling processes Two major classes of reactions mediated by samarium(II) iodide 4

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9. 2.4 Pinacol coupling processes Corey, E. J. J. Am. Chem. Soc. 2005, 127, 13813. Cozzi, F.; Siegel, J. S. Org. Biomol. Chem. 2003, 1, 157 9

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26. Many challenges need to be addressed asymmetric SmI2 -mediated cross-coupling reactions the expansion and generalization of the scope of existing reactions the design of new ligands increased mechanistic understanding of the underlying electron transfer processes 26