Login / Signup

Diastereoselective [3+2] Annulation of Aromatic/Vinylic Amides with Bicyclic Alkenes through Cobalt-Catalyzed C-H Activation and Intramolecular Nucleophilic Addition.

Parthasarathy GandeepanPachaiyappan RajamalliChien-Hong Cheng
Published in: Angewandte Chemie (International ed. in English) (2016)
A highly diastereoselective method for the synthesis of dihydroepoxybenzofluorenone derivatives from aromatic/vinylic amides and bicyclic alkenes is described. This new transformation proceeds through cobalt-catalyzed C-H activation and intramolecular nucleophilic addition to the amide functional group. Transition-metal-catalyzed C-H activation reactions of secondary amides with alkenes usually lead to [4+2] or [4+1] annulation; to the best of our knowledge, this is the first time that a [3+2] cycloaddition is described in this context. The reaction proceeds under mild conditions and tolerates a wide range of functional groups. Mechanistic studies imply that the C-H bond cleavage may be the rate-limiting step.
Keyphrases
  • transition metal
  • room temperature
  • healthcare
  • amino acid
  • reduced graphene oxide
  • carbon nanotubes
  • energy transfer
  • transcription factor
  • gold nanoparticles
  • case control