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

Abstract

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.

In-Depth Assessment of the Palladium-Catalyzed Fluorination of Five-Membered Heteroaryl Bromides

“…To date, most of the recently developed transition-metal-mediated methods for aryl fluorination 13 have seen limited application to five-membered heteroaryl systems. 14 Thus, there remains a strong need for the development of new methods for the fluorination of five-membered heteroarenes.…”

Diastereoselective Synthesis of Dialkylated Bis(phosphino)ferrocenes: Their Use in Promoting Silver‐Mediated Nucleophilic Fluorination of Chloroquinolines

“…The absence of palladium, however, left 7 unchanged. In the presence of various substoichiometric amounts of 5d , ranging from 10 to 100 mol‐% (Table , entries 2–5), the selective conversion of 7 into 8 reach up to 95 % by using 50 mol‐% of 5d (Table , entry 4) . Curiously, the addition of a larger amount of 5d was deleterious to the conversion (Table , entry 5).…”

5-Iodo-1H-1,2,3-triazoles as Versatile Building Blocks

“…One-pot synthesis of 125 I-labeled trifunctionalized reagents for multiscale imaging Noting the importance of 5-fluorotriazoles and synthetic accessibility of 5-iodotriazoles, Chu and co-workers reported the preparation of 5-fluorotriazoles by silver-mediated fluorination of 5-iodotriazoles using AgF both as a fluoride and a silver source. 133 The conditions, AgF (5 equiv), TMEDA, toluene, 120 °C, 9 h, are milder, than those used previously, 132 and the method is compatible with various functional groups. Moreover both 5-iodotriazoles without aromatic groups at C4 and bearing aliphatic substituents at N1 were smoothly converted into the corresponding 5-fluorotriazoles; 25 examples of 5-fluorotriazoles were synthesized in moderate to high yields.…”