Synthesis of 5-Fluorotriazoles by Silver-Mediated Fluorination of 5-Iodotriazoles

A simple method was developed for the direct fluorination of 5‐iodotriazoles with AgF as fluoride source and N1,N1,N2,N2‐tetramethylethane‐1,2‐diamine (TMEDA) as ligand. This method is compatible with various functional groups. 5‐Iodotriazoles without aromatic groups at the 4‐position or aliphatic substituents at the N1 position can also be smoothly converted to the corresponding 5‐fluorotriazoles. Preliminary mechanism studies were also performed. A new strategy for the direct fluorination of 5‐iodotriazoles with AgF and N1,N1,N2,N2‐tetramethylethane‐1,2‐diamine (TMEDA) is described. Substrates with aliphatic or aromatic groups at the N1 position or 4‐position can be converted to the corresponding fluorinated products in good to excellent yields. Preliminary mechanism studies were also performed.