MnBr2-Catalyzed Aerobic Oxyazidation of Fluoroolefins: Access to Fluoroalkylated β-Hydroxy Aliphatic Azides

MnBr2-catalyzed oxyazidation of fluoroolefins with molecular oxygen and TMSN3 is reported. This method gives rise to various useful fluoroalkylated beta-hydroxy aliphatic azides in 36%-97% yields. Importantly, this protocol features mild conditions, operationally simple, and gram-scalable, it tolerates various functional groups and has been applied in the synthesis of diverse attractive bioactive compounds and analogous. Mechanism studies enable the detection of the intermediate and indicate that a radical reaction process is involved. The beta-fluoride elimination of alpha-fluoroalkylated radicals via radical-polar crossover pathway was completely inhibited in this reaction.

Automated summary

MnBr2-catalyzed oxyazidation of fluoroolefins with molecular oxygen and TMSN3 provides various fluoroalkylated beta-hydroxy aliphatic azides in 36%-97% yields. This protocol features mild conditions, operational simplicity, scalability, tolerance towards different functional groups, and its application in the synthesis of diverse attractive bioactive compounds and analogues.