Regioselective Oxidative Coupling Reactions of 3-Substituted Thiophenes with Arylboronic Acids

Regioselective Oxidative Coupling Reactions of 3-Substituted Thiophenes with Arylboronic Acids

Under optimized conditions, 3-substituted thiophenes (EWG = COOEt, PO(OEt)2) undergo a facile and regioselective oxidative coupling reaction at carbon atom C4. The reactions were performed with various aryl boronic acids as nucleophiles in the presence of silver oxide (2.0 equiv), cesium trifluoroac...

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Veröffentlicht in:Organic letters 2011-07, Vol.13 (14), p.3640-3643
Hauptverfasser: Schnapperelle, Ingo, Breitenlechner, Stefan, Bach, Thorsten
Format: Artikel
Sprache:eng
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Zusammenfassung:Under optimized conditions, 3-substituted thiophenes (EWG = COOEt, PO(OEt)2) undergo a facile and regioselective oxidative coupling reaction at carbon atom C4. The reactions were performed with various aryl boronic acids as nucleophiles in the presence of silver oxide (2.0 equiv), cesium trifluoroacetate (tfa) (1.0 equiv), benzoquinone (BQ) (0.5 equiv), and catalytic amounts of Pd(tfa)2 (10 mol %) employing trifluoroacetic acid (TFA) as the solvent.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol201292v