Concise Synthesis of Dithiophene Derivatives by a Palladium- Catalyzed Multiple C-S Cross Coupling/Cyclization Sequence

The facile synthesis of new sulfur‐containing fused heterocycles was achieved by a two‐fold domino reaction consisting of a carbon‐sulfur cross‐coupling, followed by a 5‐endo‐dig cyclization. Using this strategy a series of benzo‐, thiopheno‐, pyridine‐ and pyrazino‐dithienoacenes with electron‐neut...

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Published inAdvanced synthesis & catalysis Vol. 358; no. 23; pp. 3770 - 3776
Main Authors Oechsle, Peter, Hou, Peng, Flörke, Ulrich, Paradies, Jan
Format Journal Article
LanguageEnglish
Published Blackwell Publishing Ltd 07.12.2016
Subjects
carbon-sulfur cross-coupling
Catalysis
Cross coupling
Derivatives
heteroacenes
Luminescence
palladium
Strategy
Synthesis
Synthesis (chemistry)
UV-vis spectroscopy
Voltammetry
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Summary:The facile synthesis of new sulfur‐containing fused heterocycles was achieved by a two‐fold domino reaction consisting of a carbon‐sulfur cross‐coupling, followed by a 5‐endo‐dig cyclization. Using this strategy a series of benzo‐, thiopheno‐, pyridine‐ and pyrazino‐dithienoacenes with electron‐neutral (‐C6H4‐n‐Hex), electron‐rich (‐C6H4‐NPh2) and electron‐deficient (‐C4H3N2) substituents was synthesized in high yields. The developed method was applied in the efficient synthesis of a complex donor‐acceptor molecule. The photophysical and electrochemical properties of the products were analyzed by UV‐VIS/luminescence spectroscopy and cyclic voltammetry.
Bibliography:German Science Foundations (DFG) - No. PA 1562/4-1
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ArticleID:ADSC201600802
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content type line 23
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.201600802