Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 59, Issue 2, Pages 689-694Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201910959
Keywords
alkenes; azobenzenes; C-H activation; fluorescence; palladium catalysis
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Funding
- Ministry of Science and Technology of Taiwan [MOST108-2113-M009-020-MY3, MOST104-2113-M-009-014-MY3, MOST105-2628-M-009-002-MY3]
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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.
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