Regiospecific replacement of fluorine by hydrogen in an aromatic ring induced by a rare earth organometallic

Glen B. Deacon, Craig M. Forsyth, Jun Hui Sun

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Abstract

Pentafluorobenzoic acid reacts with YbCp2(dme) to yield, after hydrolysis, 2,3,4,5-tetrafluorobenzoic acid. Conversion is near quantitative with activated magnesium as a coreductant and there is evidence for catalytic turnover in ytterbium on addition of a cyclopentadiene source. Reduction of 2,6-F2C6H3CO2H to o-FC6H4CO2H and of o-FC6H4CO2H to PhCO2H has also been achieved.

Original languageEnglish
Pages (from-to)1095-1098
Number of pages4
JournalTetrahedron Letters
Volume35
Issue number7
DOIs
Publication statusPublished - 14 Feb 1994

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