Regioselective oxidative coupling reactions of 3-substituted thiophenes with arylboronic acids

Ingo Schnapperelle; Stefan Breitenlechner; Thorsten Bach

doi:10.1021/ol201292v

Regioselective oxidative coupling reactions of 3-substituted thiophenes with arylboronic acids

Ingo Schnapperelle, Stefan Breitenlechner, Thorsten Bach

Chair of Organic Chemistry 1

Technical University of Munich

Research output: Contribution to journal › Article › peer-review

43 Scopus citations

Abstract

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.

Original language	English
Pages (from-to)	3640-3643
Number of pages	4
Journal	Organic Letters
Volume	13
Issue number	14
DOIs	https://doi.org/10.1021/ol201292v
State	Published - 15 Jul 2011

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abstract = "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.",

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T1 - Regioselective oxidative coupling reactions of 3-substituted thiophenes with arylboronic acids

AU - Schnapperelle, Ingo

AU - Breitenlechner, Stefan

AU - Bach, Thorsten

PY - 2011/7/15

Y1 - 2011/7/15

N2 - 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.

AB - 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.

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JF - Organic Letters

IS - 14

ER -

Regioselective oxidative coupling reactions of 3-substituted thiophenes with arylboronic acids

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