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A Brønsted Organic Acid Forming Solid State Salts with Chemically Stable Cationic Species

1,2-Benzenedisulfonic imide (1) is a strong Brønsted organic acid and is used for acid-catalyzed organic synthesis.1-3) For instance, 1 catalyzed acylations of alcohols with acid anhydrides can be performed under solvent-free conditions.3) After this reaction, the catalyst 1 can be recovered and reused. On the other hand, 1 can form ion-pairs with chemically stable cationic species. Barbero et al. successfully isolated cationic intermediates as solid state salts consisting of a conjugate base of 1, by the condensation reaction of aromatic aldehydes with benzimidazole derivatives under the presence of 1 to give the cationic intermediates.4) Isolated salt crystals are determined by X-ray analysis to clarify the structure of cationic intermediate.

B4139

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