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

Ingo Schnapperelle (2182508); Stefan Breitenlechner (2182506); Thorsten Bach (1397326)

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

Ingo Schnapperelle (2182508)Stefan Breitenlechner (2182506)Thorsten Bach (1397326)

Year: 2016 Journal: OPAL (Open@LaTrobe) (La Trobe University) Publisher: La Trobe University

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Abstract

Under optimized conditions, 3-substituted thiophenes (EWG = COOEt, PO(OEt)<sub>2</sub>) 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)<sub>2</sub> (10 mol %) employing trifluoroacetic acid (TFA) as the solvent.

Keywords:

Regioselectivity Catalysis Trifluoroacetic acid Nucleophile Aryl Oxidative coupling of methane Oxidative phosphorylation Carbon atom Coupling reaction

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

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