Rhodium(III)-Catalyzed Redox-Neutral Coupling of α-Trifluoromethylacrylic Acid with Benzamides through Directed C-H Bond Cleavage

Risa Yoshimoto; Yoshinosuke Usuki; Tetsuya Satoh

doi:10.1002/asia.201901776

Rhodium(III)-Catalyzed Redox-Neutral Coupling of α-Trifluoromethylacrylic Acid with Benzamides through Directed C-H Bond Cleavage

Chem Asian J. 2020 Mar 16;15(6):802-806. doi: 10.1002/asia.201901776. Epub 2020 Feb 18.

Authors

Risa Yoshimoto¹, Yoshinosuke Usuki¹, Tetsuya Satoh¹

Affiliation

¹ Department of Chemistry Graduate School of Science, Osaka City University 3-3-138 Sugimoto, Sumiyoshi-ku, Osaka, 558-8585, Japan.

PMID: 32017428
DOI: 10.1002/asia.201901776

Abstract

A rhodium(III)-catalyzed redox-neutral coupling of α-trifluoromethylacrylic acid with bezamides proceeds smoothly accompanied by amide-directed C-H bond cleavage to produce β-[2-(aminocarbonyl)phenyl]-α-trifluoromethylpropanoic acid derivatives. One of the products can be transformed to a trifluoromethyl substituted heterocyclic compound. In addition, the redox-neutral coupling of α-trifluoromethylacrylic acid with related aromatic substrates possessing a nitrogen-containing directing group can also be conducted under similar conditions.

Keywords: C−C coupling; C−H activation; alkylation; cross-coupling; rhodium.

Abstract

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