Photoredox-Catalyzed Addition of Dibromofluoromethane to Alkenes: Direct Synthesis of 1-Bromo-1-fluoroalkanes

Reported herein is a direct and efficient route to 1-bromo-1-fluoroalkanes through the reaction of unactivated alkenes with dibromofluoromethane under photoredox catalysis. The key to the success of these addition reactions is the employment of a suitable photoredox catalyst. In particular, hydro- and bromo-bromofluoromethylated products were chemoselectively formed using THF and DMF/H2O as solvents, respectively. Furthermore, the synthetic application of the prepared 1-bromo-1-fluoroalkanes has been demonstrated by their transformation into a variety of fluorine-containing compounds.

Automated summary

This study presents a direct and efficient method for the synthesis of 1-bromo-1-fluoroalkanes from unactivated alkenes and dibromofluoromethane under photoredox catalysis. The key to the success of these reactions lies in the appropriate choice of photoredox catalyst. The prepared 1-bromo-1-fluoroalkanes can be further transformed into various fluorine-containing compounds.