Protonated carbonic acid and reactive intermediates in the acidic decarboxylation of indolecarboxylic acids.
2012
Elucidation of the mechanism for decarboxylation of indolecarboxylic acids over a wide range of solution acidity reveals the importance of protonated carbonic acid (PCA) as a reaction intermediate. In concentrated acid, the initial addition of water to the carboxyl group of the indolecarboxylic acid leads to a hydrated species that is capable of releasing PCA upon rate-determining carbon–carbon bond cleavage. The overall process is catalytic in water and acid, implicating PCA as a potential carboxylating reagent in the microscopic reverse reaction.
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