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20.2.10.1.2 Method 2: Palladium-Mediated C—H Activation and Carboxylation

DOI: 10.1055/sos-SD-020-00506

Yoon, T. P.; Jacobsen, E. N.Science of Synthesis, (200720535.

Palladium(II) complexes promote direct metalation of arenes, and the resulting σ-complexes can be induced to undergo carboxylation in the presence of carbon dioxide or carbon monoxide in acidic solvents (Scheme 4).[‌15‌] Palladium(II) acetate alone induces this transformation stoichiometrically,[‌16‌] but the use of potassium persulfate in trifluoroacetic acid allows the reaction to proceed with catalytic amounts of the transition-metal complex when used to synthesize benzoic acid (1) from benzene.[‌17‌] The mechanism of the reaction is proposed to involve an initial attack on the arene by an electrophilic palladium(II) species, and the regioselectivities observed in the carboxylation, while modest, are consistent with those expected from an electrophilic aromatic substitution. In addition, electron-poor arenes such as benzoic acid and nitrobenzene do not react under these conditions.

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