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Metal-Free Catalytic Reductive Cleavage of Enol Ethers.

Karina ChulskyRoman Dobrovetsky
Published in: Organic letters (2018)
In contrast to the well-known reductive cleavage of the alkyl-O bond, the cleavage of the alkenyl-O bond is much more challenging especially using metal-free approaches. Unexpectedly, alkenyl-O bonds were reductively cleaved when enol ethers were reacted with Et3SiH and a catalytic amount of B(C6F5)3. Supposedly, this reaction is the result of a B(C6F5)3-catalyzed tandem hydrosilylation reaction and a silicon-assisted β-elimination. A mechanism for this cleavage reaction is proposed based on experiments and density functional theory (DFT) calculations.
Keyphrases
  • density functional theory
  • dna binding
  • molecular dynamics
  • electron transfer
  • magnetic resonance
  • transcription factor
  • crystal structure
  • ionic liquid
  • magnetic resonance imaging
  • computed tomography