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Divergent Carbocatalytic Routes in Oxidative Coupling of Benzofused Heteroaryl Dimers: A Mechanistic Update.

David S CasadioSanteri AikonenAnna LenardaMartin NiegerTao HuStefan TaubertDage SundholmMikko MuuronenTom WirtanenJuho Helaja
Published in: Chemistry (Weinheim an der Bergstrasse, Germany) (2021)
Mildly thermal air or HNO3 oxidized activated carbons catalyse oxidative dehydrogenative couplings of benzo[b]fused heteroaryl 2,2'-dimers, e.g., 2-(benzofuran-2-yl)-1H-indole, to chiral 3,3'-coupled cyclooctatetraenes or carbazole-type migrative products under O2 atmosphere. DFT calculations show that the radical cation and the Scholl-type arenium cation mechanisms lead to different products with 2-(benzofuran-2-yl)-1H-indole, being in accord with experimental product distributions.
Keyphrases
  • ionic liquid
  • density functional theory
  • molecular dynamics
  • molecular dynamics simulations
  • molecular docking
  • monte carlo