Liang S, et al. Journal of Fluorine Chemistry, 2017, 203, 136-139.
The DMPU-HF complex has been demonstrated as an efficient fluorinating reagent for the bromofluorination of alkenes, offering a highly regioselective approach to the synthesis of bromofluorinated compounds. In a typical experimental procedure, alkenes (0.20 mmol) were dissolved in dichloromethane (1 mL) along with N-bromosuccinimide (NBS, 53.4 mg, 0.3 mmol) in a plastic vial. To this mixture, DMPU-HF (41.2 μL, 1.4 mmol) was added, and the reaction was allowed to stir at room temperature for 24 hours. Following completion, the reaction mixture was quenched with water (2 mL) and extracted with dichloromethane (3 × 2 mL). The combined organic extracts were dried over sodium sulfate and concentrated under reduced pressure. Purification via flash chromatography on silica gel (eluent: 9:1 hexanes/ethyl acetate) yielded the desired bromofluorinated products, often as regioisomeric mixtures. This methodology highlights the high reactivity and Markovnikov selectivity of DMPU-HF in enabling the efficient formation of valuable fluorinated building blocks for biologically active molecule synthesis.
Okoromoba O. E., et al. Organic Letters, 2015, 17(16), 3975-3977.