DMPU-HF Reagent

Application

DMPU-HF Reagent is a nucleophilic fluorination reagent that can be used:       

• To prepare fluoroalkenes and gem-difluoromethlylene from substituted alkynes in the presence of an Au-JohnPhos complex as a catalyst.      
• To synthesize substituted 4-fluorotetrahydropyrans and 4-fluoropiperidines from homoallylic alcohol/amine with aldehyde via fluoro-Prins reaction.       
• In the bromofluorination of alkenes in the presence of N-bromosuccinimide to yield corresponding bromofluoro compounds.

DMPU-HF, like TREAT-HF and Olah′s Reagent, is a convenient way of utilizing Hydrogen Fluoride as a fluorination reagent. However, unlike TREAT-HF and Olah′s Reagent, DMPU-HF is more tolerant of transition metals due to the reduced basicity of DMPU, compared to Triethylamine and Pyridine. Hammond and coworkers display its compatibility in transition-metal catalysis in gold-catalyzed mono- and difluoroination of alkynes.

Other Notes

Designer HF-Based Fluorination Reagent: Highly Regioselective Synthesis of Fluoroalkenes and gem-Difluoromethylene Compounds from Alkynes