Tandem decarboxylation/fluorination of N-acetylanthranilic acids by iridium complexes

•A new method for the synthesis of organofluorine compounds bearing fluoroaryl structures has been developed.•N-acetylanthranilic acids undergo decarboxylative fluorination in the presence of cationic iridium complexes.•New synthetic applications of the catalytic decarboxylation of aromatic carboxyl...

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Bibliographic Details
Published in:Journal of fluorine chemistry 2024-02, Vol.274, p.110260, Article 110260
Main Authors: Shirai, Tomohiko, Yamasaki, Tomokazu
Format: Article
Language:English
Subjects:
C(sp2)-F bond formation
Decarboxylative fluorination
Iridium catalyst
Organofluorine compounds
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Summary:•A new method for the synthesis of organofluorine compounds bearing fluoroaryl structures has been developed.•N-acetylanthranilic acids undergo decarboxylative fluorination in the presence of cationic iridium complexes.•New synthetic applications of the catalytic decarboxylation of aromatic carboxylic acids to produce C(sp2)–F bonds. Decarboxylative transformations are valuable tools for carbon-heteroatom bond formation. However, synthetic applications of the decarboxylation of aromatic carboxylic acids to produce C(sp2)–F bonds remain limited. Herein, we propose a tandem catalytic decarboxylation/fluorination of N-acetylanthranilic acids to produce useful organofluorine compounds by using Ir(I)/bisphosphine complexes. [Display omitted]
ISSN:0022-1139
1873-3328
DOI:10.1016/j.jfluchem.2024.110260