Lewis Base Catalyzed Hydrofluorination of Aziridines

Doyle et al. have reported 1,5-diazabicyclo[4.3.0]-5-nonene (DBN) catalyzed hydrofluorination of aziridines to provide beta-fluoroamines. In this reaction, the non-nucleophilic alcohol 1,1,1,3,3,3-hexafluoro-2-propanol (HFIP) acts as a proton source and in situ generated DBN• (HF)n prepared from HFIP, benzoyl fluoride and DBN, is used for a hydrofluorination reagent. A glass flask may be used and the reaction may be performed on a gram scale without exclusion of air or moisture.