Cascade One-Pot Synthesis of Orange-Red-Fluorescent Polycyclic Cinnolino[2,3-f]phenanthridin-9-ium Salts by Palladium(II)-Catalyzed C-H Bond Activation of 2-Azobiaryl Compounds and Alkenes

Jayachandran Jayakumar, Guganchandar Vedarethinam, Huan-Chang Hsiao, Shang-You Sun, Shih-Ching Chuang*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

5 Scopus citations

Abstract

Quaternary ammonium salts were synthesized in moderate to good yields through double oxidative C-H bond activation on azobenzenes. The mechanism of the highly regioselective reaction of 2-azobiaryls with alkenes to give orange-red-fluorescent cinnolino[2,3-f]phenanthridin-9-ium salts and 15H-cinnolino[2,3-f]phenanthridin-9-ium-10-ide is proposed to involve ortho C-H olefination of the 2-azobiaryl compound with the alkene, intramolecular aza-Michael addition, concerted metalation-deprotonation (CMD), reductive elimination, and oxidation.

Original languageEnglish
Pages (from-to)689-694
Number of pages6
JournalAngewandte Chemie - International Edition
Volume59
Issue number2
DOIs
StatePublished - 7 Jan 2020

Keywords

  • alkenes
  • azobenzenes
  • C-H activation
  • fluorescence
  • palladium catalysis
  • CROSS-COUPLING REACTIONS
  • LIGHT-EMITTING-DIODES
  • RHODIUM(III)-CATALYZED SYNTHESIS
  • CINNOLINIUM SALTS
  • AMMONIUM-SALTS
  • N-HETEROCYCLES
  • PALLADIUM
  • OLEFINATION
  • FUNCTIONALIZATION
  • ALKENYLATION

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