Three‐Component Synthesis of Quinolines Based on Radical Cascade Visible‐Light Photoredox Catalysis

Synthesis of highly substituted quinolines has been developed based on three‐component radical cascade based on visible‐light photoredox catalysis. This tandem coupling reaction has been coordinated to proceed with high chemoselectivity based on the differential electronic properties of coupling par...

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Bibliographic Details
Published inAdvanced synthesis & catalysis Vol. 360; no. 18; pp. 3553 - 3562
Main Authors Choi, Jun‐Ho, Park, Cheol‐Min
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 17.09.2018
Wiley Subscription Services, Inc
Subjects
Alkenes
Catalysis
Chemical synthesis
Chemistry
Chemistry, Applied
Chemistry, Organic
Coupling
Halides
Multicomponent reaction
N-heterocycle
Organic compounds
Oxidation
Photoredox catalysis
Physical Sciences
Quinoline
Radical cascade reaction
Science & Technology
N-heterocycle
STYRENES
Multicomponent reaction
GOLD CATALYSIS
ALKYNES
BROMIDES
HIGHLY EFFICIENT
Photoredox catalysis
FUNCTIONALIZATION
MULTICOMPONENT REACTIONS
ALKENES
Quinoline
Radical cascade reaction
AEROBIC OXIDATIVE CYCLIZATION
SUBSTITUTED QUINOLINES
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Summary:Synthesis of highly substituted quinolines has been developed based on three‐component radical cascade based on visible‐light photoredox catalysis. This tandem coupling reaction has been coordinated to proceed with high chemoselectivity based on the differential electronic properties of coupling partners. Subjection of electron‐rich β‐aminoacrylates with electron‐deficient halides and alkenes to the optimized conditions leads to the formation of quinolines in good yields after in situ oxidation of tetrahydroquinolines. Detailed mechanistic studies which reveal an unexpected reaction pathway is described.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.201800734