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Synfacts 2014; 10(1): 0075
DOI: 10.1055/s-0033-1340375
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart · New York

Synthesis of 2,5-Diarylated Thiophene 1,1-Dioxides

Rezensent(en):
Paul Knochel
,
Nadja M. Barl
Tsai C.-H, Chirdon DN, Maurer AB, Bernhard S, Noonan KJ. T * Carnegie Mellon University, Pittsburgh, USA
Synthesis of Thiophene 1,1-Dioxides and Tuning Their Optoelectronic Properties.

Org. Lett. 2013;
15: 5230-5233
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Publikationsverlauf

Publikationsdatum:
13. Dezember 2013 (online)

 
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Key words

tin - palladium - thiophene dioxides

Significance

The authors disclose the palladium-catalyzed diarylation of distannylated thiophene 1,1-dioxide (electron-poor aryl coupling partners) and diiodo thiophene 1,1-dioxide (electron-rich aryl coupling partners) by Stille cross-coupling reactions to synthesize various 2,5-bis(aryl)thiophene 1,1-dioxides in moderate yields. Furthermore, the electrochemical and photophysical properties of these diarylated thiophene dioxides were investigated using cyclic voltammetry and fluorescence spectroscopy.


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Comment

The corresponding distannylated thiophene 1,1-dioxides are obtained by treatment of 2,5-bis(trimethylsilyl)thiophene 1,1-dioxide with tetrabutylammonium fluoride (TBAF) and bis(tributyltin) oxide. A wide range of these diarylated thiophene dioxides show significant quantum yields, and their appropriate reduction and oxidation ­potentials may easily be tuned by the use of ­electron-donating and -withdrawing aryl groups.


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