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- Title
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.
- Authors
Jayakumar, Jayachandran; Vedarethinam, Guganchandar; Hsiao, Huan‐Chang; Sun, Shang‐You; Chuang, Shih‐Ching
- 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.
- Subjects
HECK reaction; ALKENES; PALLADIUM; QUATERNARY ammonium salts; REGIOSELECTIVITY (Chemistry); SALTS
- Publication
Angewandte Chemie, 2020, Vol 132, Issue 2, p699
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201910959