2019
DOI: 10.1002/ange.201910959
|View full text |Cite
|
Sign up to set email alerts
|

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

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 … Show more

Help me understand this report

Search citation statements

Order By: Relevance

Paper Sections

Select...
1
1

Citation Types

0
2
0

Year Published

2020
2020
2024
2024

Publication Types

Select...
5

Relationship

0
5

Authors

Journals

citations
Cited by 5 publications
(2 citation statements)
references
References 116 publications
0
2
0
Order By: Relevance
“…In 2020, Chuang and co-workers synthesized orange-red-fluorescent cinnolino[2,3- f ]phenanthridin-9-ium salts and 15 H -cinnolino[2,3- f ]phenanthridin-9-ium-10-ide from azobenzenes (Scheme 50 ). 153 The reaction mechanism involves a palladium(II)-catalyzed double oxidative C–H activation of azobenzenes. After the first C–H activation, a six-membered palladacycle is formed that inserts into the alkene and results in the ortho -alkenylated azobenzene via β-hydride elimination.…”
Section: C–h Activation Pathways In the Creation And Modification Of ...mentioning
confidence: 99%
“…In 2020, Chuang and co-workers synthesized orange-red-fluorescent cinnolino[2,3- f ]phenanthridin-9-ium salts and 15 H -cinnolino[2,3- f ]phenanthridin-9-ium-10-ide from azobenzenes (Scheme 50 ). 153 The reaction mechanism involves a palladium(II)-catalyzed double oxidative C–H activation of azobenzenes. After the first C–H activation, a six-membered palladacycle is formed that inserts into the alkene and results in the ortho -alkenylated azobenzene via β-hydride elimination.…”
Section: C–h Activation Pathways In the Creation And Modification Of ...mentioning
confidence: 99%
“…Owing to these wide range of applications, the development of new methods for the synthesis of cationic N -heterocycles has gained significant traction in recent years. Notable methods for the synthesis of N -heterocycle-fused cationic organic compounds are ring-closing metathesis (Scheme a), Rh-catalyzed C–H activation (Scheme b), Pd-catalyzed C–H activation (Scheme c), Au-catalyzed cyclization (Scheme d), Cu-mediated C–H activation–cyclization (Scheme e), intramolecular radical arylation, and oxidative photocyclization, among others . Many of these methods, in particular C–H activation methods which have witnessed meteoric growth, require stoichiometric or catalytic amount of precious metal salts/complexes and rigorous conditions.…”
Section: Introductionmentioning
confidence: 99%