Potassium thioacetate

Abstract

Potassium thioacetate (AcSK) is an off-white to lightbrown crystalline powder that is air sensitive, hygroscopic, and commercially available. It is soluble in water and stable under standard temperature and pressure (m.p. 173–176 °C). This reagent is widely used as a sulfur source in the synthesis of sulfur-containing organic compounds. The formation of C–S bonds can be easily accomplished by reacting potassium thioacetate with aryl, benzyl, alkyl and vinyl halides or arenediazonium salts, to obtain the corresponding thioesters. A later deprotection allows straightforward access to the thiol since acyl groups may be removed under mild conditions. Thus, potassium thioacetate is a versatile reagent that can participate in numerous reactions such as nucleophilic substitutions, transition-metal-catalyzed couplings, photoinduced substitutions, vinylic substitutions and reductive amidation of nitro arenes. Therefore, this reagent has been employed for the synthesis of heterocycles,1 polymers,2 transition-metal ligands,3 nanoparticles,4 bioactive compounds5 and macromolecular inclusion complexes