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Preparation and Use of Samarium Diiodide (SmI2) in Organic Synthesis: The Mechanistic Role of HMPA and Ni(II) Salts in the Samarium Barbier Reaction
Journal JoVE
Chimie
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Journal JoVE Chimie
Preparation and Use of Samarium Diiodide (SmI2) in Organic Synthesis: The Mechanistic Role of HMPA and Ni(II) Salts in the Samarium Barbier Reaction

Preparation and Use of Samarium Diiodide (SmI2) in Organic Synthesis: The Mechanistic Role of HMPA and Ni(II) Salts in the Samarium Barbier Reaction

DOI:
10.3791/4323-v

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12:22 min

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February 04, 2013

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, ,
1Department of Chemistry,Lehigh University

Chapitres

  • 00:05Titre
  • 01:54Synthesis of 0.1 M Samarium Diiodide
  • 04:06Samarium Barbier Reaction-hexamethylphosphoramide (HMPA) Addition
  • 06:56Samarium Barbier Reaction-Ni(acac)2 Catalyst
  • 08:56Results: The Impact of Additives on the Mechanism of the Samarium Barbier Reaction
  • 11:51Conclusion

Summary

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A straightforward procedure for the preparation of samarium diiodide (SmI2) in THF is described. The role of two main additives namely hexamethylphosphoramide (HMPA) and Ni(acac)2 in Sm mediated reactions is demonstrated in the Sm-Barbier reaction.

Tags

Samarium DiiodideSmI2Organic SynthesisHMPANi(II) SaltsSamarium Barbier ReactionReagentSynthetic Organic ChemistsMolecular IodineTHFSingle Electron ReductantC-C Bond-forming ReactionsCascade ReactionsSequential ReactionsFunctional GroupsSulfoxidesSulfonesPhosphine OxidesEpoxidesAlkyl HalidesAryl HalidesCarbonylsConjugated Double BondsCosolventsAdditivesLewis BasesProton SourcesInorganic AdditivesMechanism Of SmI2 Reactions

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