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Photodriven Sm(III)-to-Sm(II) Reduction for Catalytic Applications.

Christian M Johansen1, Emily A Boyd1, Drew E Tarnopol1

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Photochemical methods regenerate samarium diiodide (SmI₂) from samarium(III) for catalytic applications. This approach enables Sm-catalyzed reductive cross-coupling reactions without harsh additives.

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Area of Science:

  • Organic Chemistry
  • Photochemistry
  • Catalysis

Background:

  • Samarium diiodide (SmI₂) is a versatile one-electron reductant.
  • Catalytic applications require efficient regeneration of SmI₂ from Sm(III) species.
  • Regenerating Sm(III)-alkoxides to Sm(II) is critical for samarium-catalyzed transformations.

Purpose of the Study:

  • To develop photochemical methods for regenerating SmI₂ from SmI₃ and Sm(III)-alkoxides.
  • To demonstrate the utility of these methods in a catalytic reductive cross-coupling reaction.

Main Methods:

  • Photochemical reduction of SmI₃ and a model Sm(III)-alkoxide to SmI₂(THF)n using Hantzsch ester as a direct photoreductant or an Ir-photoredox catalyst.
  • Utilizing Hantzsch ester as a reductive quencher in Ir-based photoredox catalysis.
  • Investigating SmI₂ generation in the presence of various additives (protic, chiral, Lewis basic).

Main Results:

  • Successful photochemical generation of SmI₂(THF)n from SmI₃ and a Sm(III)-alkoxide.
  • Demonstrated SmI₂ regeneration without Lewis acidic additives, enabling selective ligand coordination.
  • Facilitated SmI₂ generation in the presence of diverse functional groups.
  • Proof-of-concept: Photodriven, Sm-catalyzed intermolecular ketone-acrylate coupling achieved.

Conclusions:

  • Photochemical regeneration of SmI₂ is feasible using Hantzsch ester or Ir-photoredox catalysis.
  • This method allows for Sm-catalyzed reductive cross-coupling reactions under mild conditions.
  • The developed methodology offers a sustainable and efficient route for samarium-based catalysis.