Fluoroalkyl sulfides as photoredox-active coupling reagents for alkene difunctionalization

A visible-light-promoted fluoroalkylation-thiolation of alkenes is described. A 4-tetrafluoropyridinylthio fragment serves as a photoredox-active group in the initiation step and undergoes a radical group transfer, which is important for the reaction efficiency. In the primary products, the pyridiny...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2020-08, Vol.56 (66), p.9453-9456
Main Authors: Kosobokov, Mikhail D, Zubkov, Mikhail O, Levin, Vitalij V, Kokorekin, Vladimir A, Dilman, Alexander D
Format: Article
Language:English
Subjects:
Alkenes
Alkenes - chemistry
Alkylation
Coupling (molecular)
Crystallography
Halogenation
Imines - chemical synthesis
Imines - chemistry
Light
Magnetic Resonance Spectroscopy
NMR
Nuclear magnetic resonance
Oxidation-Reduction
Reagents
Stereoisomerism
Substitution reactions
Sulfides - chemistry
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Description
Summary:A visible-light-promoted fluoroalkylation-thiolation of alkenes is described. A 4-tetrafluoropyridinylthio fragment serves as a photoredox-active group in the initiation step and undergoes a radical group transfer, which is important for the reaction efficiency. In the primary products, the pyridinylthio substituent may be further functionalized via radical processes or an aromatic substitution reaction. A visible-light-promoted fluoroalkylation-thiolation of alkenes is described.
ISSN:1359-7345
1364-548X
DOI:10.1039/d0cc04617e