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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
Author(s) -
Jayakumar Jayachandran,
Vedarethinam Guganchandar,
Hsiao HuanChang,
Sun ShangYou,
Chuang ShihChing
Publication year - 2020
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201910959
Subject(s) - chemistry , regioselectivity , alkene , intramolecular force , deprotonation , palladium , metalation , medicinal chemistry , catalysis , fluorescence , reductive elimination , orange (colour) , photochemistry , stereochemistry , organic chemistry , ion , physics , food science , quantum mechanics
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 15 H ‐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.