title: Carboxyl radical-assisted 1,5-aryl migration through Smiles rearrangement.
abstract: 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.
authors.affiliation: Organic and Medicinal Chemistry Division, CSIR-Indian Institute of Chemical Biology, 4 Raja S. C. Mullick Road, Jadavpur, Kolkata-700032, West Bengal, India and Academy of Scientific and Innovative Research (AcSIR), Kolkata-700032, West Bengal, India. rjana@iicb.res.in.
authors.forename: Asik
authors.initials: A
authors.lastname: Hossian
authors.affiliation: Organic and Medicinal Chemistry Division, CSIR-Indian Institute of Chemical Biology, 4 Raja S. C. Mullick Road, Jadavpur, Kolkata-700032, West Bengal, India and Academy of Scientific and Innovative Research (AcSIR), Kolkata-700032, West Bengal, India. rjana@iicb.res.in.
authors.forename: Ranjan
authors.initials: R
authors.lastname: Jana