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We report herein, a silver(I)-catalyzed Smiles rearrangement of 2-aryloxy- or 2-(arylthio)benzoic acids to provide aryl-2-hydroxybenzoate or aryl-2-mercaptobenzoate dimer, respectively, through 1,5-aryl migration from oxygen or sulfur to carboxylate oxygen. Mechanistically, the aryl ether moiety undergoes an intramolecular ipso attack by the carboxyl radical followed by a C–O or C–S bond cleavage. Aryl-2-mercaptobenzoates undergo oxidative dimerization through a thiol moiety in situ.

Graphical abstract: Carboxyl radical-assisted 1,5-aryl migration through Smiles rearrangement

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