posted on 2020-01-08, 16:36authored byAnne-Marie Wakuluk-Machado, Damien F. Dewez, Hajar Baguia, Miguel Imbratta, Pierre-Georges Echeverria, Gwilherm Evano
A simple,
efficient, cheap, and broadly applicable system for the
carboxylation of benzylic bromides with carbon monoxide and water
is reported. Upon simple reaction with only 2.5 wt % of Pearlman’s
catalyst and 10 mol % of tetrabutylammonium bromide in tetrahydrofuran
at 110 °C for 4 h, a range of benzylic bromides can be smoothly
converted to the corresponding arylacetic acids in good to excellent
yields after simple extraction and acid–base wash. The reaction
was found to be broadly applicable, scalable, and could be successfully
extended to the use of ex situ-generated carbon monoxide and applied
to the synthesis of the nonsteroidal anti-inflammatory drug diclofenac.