Iron-Catalyzed Thioarylation of Arenes Using Saccharin-Derived Reagents

Biaryl sulfides are important scaffolds found in various natural products and pharmaceutically active compounds. One of the main approaches for the synthesis of this compound class involves the substitution of arenes using electrophilic thioaryl species. However, these methods generally require acidic activation of the electrophile, more forcing conditions, and long reaction times. Here, we describe the combination of the super Lewis acid iron(III) triflimide with saccharin-based thioarylation reagents for the rapid synthesis of unsymmetrical biaryl sulfides under mild conditions. This approach was effective with electron-deficient thioaryl species that performed poorly with previous methods, allowing the efficient functionalization of bioactive compounds.