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Pd(OH)2/C, a Practical and Efficient Catalyst for the Carboxylation of Benzylic Bromides with Carbon Monoxide

par Wakuluk-Machado, Anne-Marie;Dewez, Damien ;Baguia, Hajar ;Imbratta, Miguel;Echeverria, Pierre-Georges;Evano, Gwilherm
Référence Organic process research & development, 24, page (713-723)
Publication Publié, 2020-01-01

Article révisé par les pairs

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Résumé :

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 TBAB in THF at 110 °C for 4 hours, 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 non-steroidal anti-inflammatory drug diclofenac.