Silver-mediated fluorination, trifluoromethylation, and trifluoromethylthiolation of arynes

Abstract

General approaches for fluorination, trifluoromethylation, and trifluoromethylthiolation were developed based on the electrophilic nature of arynes. In these reactions, the addition of fluorine-containing nucleophiles onto aryne intermediates was efficiently promoted by either silver catalysts or silver-containing stoichiometric reagents. Contrary to known methods that require aromatic precursors, our new approach enables efficient non-traditional synthesis of Ar–F, Ar–CF₃ and Ar–SCF₃ from non-aromatic building blocks under relatively mild conditions.