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3-Bromo-1,1,1-trifluoroacetone was first disclosed as an effective indirect trifluoromethylation reagent to construct the important 3-trifluoromethyl isocoumarin skeleton. The reaction proceeds through a ligand-promoted, iridium-catalyzed ortho-selective C-H alkylation of benzoic acid… Click to show full abstract
3-Bromo-1,1,1-trifluoroacetone was first disclosed as an effective indirect trifluoromethylation reagent to construct the important 3-trifluoromethyl isocoumarin skeleton. The reaction proceeds through a ligand-promoted, iridium-catalyzed ortho-selective C-H alkylation of benzoic acid and an intermolecular cyclization reaction promoted by silver acetate. A wide range of 3-trifluoromethyl isocoumarins can be easily obtained in moderate to good yields. Importantly, the isocoumarin skeleton can be easily formed in bioactive compounds, highlighting the importance of this reaction.
Journal Title: Organic letters
Year Published: 2020
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