Abstract
Direct ethoxycarbonyldifluoromethylation of aromatic compounds by BrCF 2CO 2Et was investigated using Fenton reagent in dimethylsulfoxide. Various five-membered hetero-aromatic compounds, benzene derivatives and uracil having ethoxycarbonyldifluoromethyl group were obtained catalytically with the combination of ferrocene and H 2O 2 at room temperature. The ethoxycarbonyldifluoromethylation occurred at the position predicted by the trend of the electrophilic substitution of aromatic compounds. When para-substituted aniline derivatives were used as a substrate, the one-pot synthesis of 3,3-difluoro-2,3-dihydroindole-2-one derivatives was achieved through the ethoxycarbonyldifluoromethylation at the ortho-position to the amino group and the consecutive intramolecular amidation of the amino group and the adjacent ethoxycarbonyldifluoromethyl group.
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