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Chemoselective Ru-Catalyzed Oxidative Lactamization vs Hydroamination of Alkynylamines: Insights from Experimental and Density Functional Theory Studies.

Andrés M Álvarez-ConstantinoAndrea Álvarez-PérezJesús A VarelaGiuseppe SciortinoGregori UjaqueCarlos Saá
Published in: The Journal of organic chemistry (2022)
The Ru-catalyzed intramolecular oxidative amidation (lactamization) of aromatic alkynylamines with 4-picoline N -oxide as an external oxidant has been developed. This chemoselective process is very efficient to achieve medium-sized ε- and ζ-lactams (seven- and eight-membered rings) but not for the formation of common δ-lactams (six-membered rings). DFT studies unveiled the capital role of the chain length between the amine and the alkyne functionalities: the longer the connector, the more favored the lactamization process vs hydroamination.
Keyphrases
  • density functional theory
  • molecular dynamics
  • energy transfer
  • room temperature
  • case control
  • amino acid
  • quantum dots
  • ionic liquid