title: Metal-free radical thiolations mediated by very weak bases.
abstract: Aromatic thioethers and analogous heavier chalcogenides were prepared by reaction of arene-diazonium salts with disulfides in the presence of the cheap and weak base NaOAc. The mild and practical reaction conditions (equimolar reagents, DMSO, r.t., 8 h) tolerate various functional groups (e.g. Br, Cl, NO2, CO2R, OH, SCF3, furans). Mechanistic studies indicate the operation of a radical aromatic substitution mechanism via aryl, acetyloxyl, thiyl, and dimsyl radicals.
authors.affiliation: Institute of Organic Chemistry, University of Regensburg, Germany. axel.jacobi@ur.de.
authors.forename: Denis
authors.initials: D
authors.lastname: Koziakov
authors.forename: Michal
authors.initials: M
authors.lastname: Majek
authors.forename: Axel
authors.initials: A
authors.lastname: Jacobi von Wangelin