Silver-mediated fluorination, trifluoromethylation, and trifluoromethylthiolation of arynes

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.