118. The application of samarium(II) iodide in organic synthesis

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Mingli Li
2014-6-7
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(stored as THF solutions, blue-green for SmI2 and yellow-green for YbI2 )
Deoxygenation Reactions
Reductions of Double Bonds
SmI2
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.
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Two major classes of reactions mediated by samarium(II) iodide
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
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Functional group reduction
Procter. D. J. Chem. Rev., Articles ASAP
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2.1 Barbier–Grignard processes
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2.2 Radical alkene addition reactions
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2.3 Ketyl radical alkene addition reactions
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2.4 Pinacol coupling processes
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3 Cross-Coupling As Part of Sequential and Cascade Reactions
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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
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