Phase Transfer Catalyzed Melt Synthesis of Diaryl Sulfides

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Abstract
The phase transfer catalyzed interaction of sodium sulfide with molten aryl halides is described. The yields of diaryl sulfide are greater than 50% when activating groups such as cyano, nitro, phthalimido, and anhydrido are present on the aromatic ring. In the absence of these activating groups the yields are less than 2%. The effect of parameters such as reaction temperature, reactant concentration and the nature of the phase transfer catalyst on the reaction yields are also reported. This procedure is especially useful for activated substrates that are sensitive to side reactions in dipolar aprotic solvents.