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

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‐cinnoli...

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Published inAngewandte Chemie International Edition Vol. 59; no. 2; pp. 689 - 694
Main Authors Jayakumar, Jayachandran, Vedarethinam, Guganchandar, Hsiao, Huan‐Chang, Sun, Shang‐You, Chuang, Shih‐Ching
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 07.01.2020
Subjects
alkenes
azobenzenes
Chemistry
Chemistry, Multidisciplinary
C−H activation
fluorescence
palladium catalysis
Physical Sciences
Science & Technology
palladium catalysis
PALLADIUM
azobenzenes
RHODIUM(III)-CATALYZED SYNTHESIS
CINNOLINIUM SALTS
OXIDATIVE ANNULATION
alkenes
AMMONIUM-SALTS
LIGHT-EMITTING-DIODES
CROSS-COUPLING REACTIONS
C-H activation
fluorescence
ALKENYLATION
ISOQUINOLINIUM SALTS
N-HETEROCYCLES
C−H activation
Online AccessGet full text
ISSN1433-7851
1521-3773
DOI10.1002/anie.201910959

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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. Fired up: Orange‐red‐fluorescent cinnolino[2,3‐f]phenanthridin‐9‐ium salts were synthesized with high regioselectivity from 2‐azobiaryls and alkenes by palladium(II)‐catalyzed C−H activation under mild reaction conditions (see scheme). The prepared quaternary ammonium salts showed strong fluorescence emission maxima at 575–620 nm with broad bandwidths.
AbstractList 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. Fired up: Orange‐red‐fluorescent cinnolino[2,3‐f]phenanthridin‐9‐ium salts were synthesized with high regioselectivity from 2‐azobiaryls and alkenes by palladium(II)‐catalyzed C−H activation under mild reaction conditions (see scheme). The prepared quaternary ammonium salts showed strong fluorescence emission maxima at 575–620 nm with broad bandwidths.
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.
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.
Author Vedarethinam, Guganchandar
Jayakumar, Jayachandran
Sun, Shang‐You
Hsiao, Huan‐Chang
Chuang, Shih‐Ching
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  givenname: Guganchandar
  surname: Vedarethinam
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  givenname: Huan‐Chang
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  givenname: Shang‐You
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  organization: National Chiao Tung University
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  givenname: Shih‐Ching
  orcidid: 0000-0002-6926-9812
  surname: Chuang
  fullname: Chuang, Shih‐Ching
  email: jscchuang@faculty.nctu.edu.tw
  organization: National Chiao Tung University
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Issue 2
Keywords palladium catalysis
PALLADIUM
azobenzenes
RHODIUM(III)-CATALYZED SYNTHESIS
CINNOLINIUM SALTS
OXIDATIVE ANNULATION
alkenes
AMMONIUM-SALTS
LIGHT-EMITTING-DIODES
CROSS-COUPLING REACTIONS
C-H activation
fluorescence
ALKENYLATION
ISOQUINOLINIUM SALTS
N-HETEROCYCLES
C−H activation
Language English
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Notes Dedicated to Prof. Chien‐Hong Cheng
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e_1_2_2_10_2
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e_1_2_2_26_3
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e_1_2_2_45_2
e_1_2_2_87_2
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e_1_2_2_68_1
e_1_2_2_60_2
e_1_2_2_57_3
e_1_2_2_11_2
e_1_2_2_38_2
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e_1_2_2_72_2
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SSID ssj0028806
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Snippet Quaternary ammonium salts were synthesized in moderate to good yields through double oxidative C−H bond activation on azobenzenes. The mechanism of the highly...
Quaternary ammonium salts were synthesized in moderate to good yields through double oxidative C-H bond activation on azobenzenes. The mechanism of the highly...
Source Web of Science
SourceID pubmed
webofscience
crossref
wiley
SourceType Index Database
Enrichment Source
Publisher
StartPage 689
SubjectTerms alkenes
azobenzenes
Chemistry
Chemistry, Multidisciplinary
C−H activation
fluorescence
palladium catalysis
Physical Sciences
Science & Technology
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
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https://www.ncbi.nlm.nih.gov/pubmed/31617286
Volume 59
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