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J Org Chem. 2012 Aug 3;77(15):6505-9. doi: 10.1021/jo301032f. Epub 2012 Jul 24.

Protonated carbonic acid and reactive intermediates in the acidic decarboxylation of indolecarboxylic acids.

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Davenport Research Laboratories, Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, Ontario, Canada M5S3H6.


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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