arylthiolates

Arylthiolates are chemical compounds characterized by the presence of an aryl group directly bonded to a sulfur atom that carries a negative charge. This means the sulfur atom is deprotonated from an arylthiol (also known as a thiophenol). The general formula can be represented as Ar-S⁻, where Ar denotes an aromatic ring system and S⁻ represents the negatively charged sulfur atom.

These species are important intermediates and reagents in organic synthesis. Due to the negative charge on the sulfur atom, arylthiolates are nucleophilic and can participate in various reactions. They are commonly employed in nucleophilic substitution reactions, where they can displace leaving groups to form new carbon-sulfur bonds. This is a key step in the synthesis of aryl sulfides.

Arylthiolates can be generated by the deprotonation of arylthiols using a base, such as alkali metal hydroxides, alkoxides, or organometallic reagents. The stability of arylthiolates is influenced by the electronic properties of the aryl ring; electron-withdrawing substituents on the ring can stabilize the negative charge, making the corresponding arylthiol more acidic and its thiolate easier to form. They are also utilized in palladium-catalyzed cross-coupling reactions and as ligands in coordination chemistry.