Nucleophilic Substitution of Selenosulfonates with Me3SiCF2Br: Facile and Efficient Access to Bromodifluoromethylated Selenides under Metal-Free Conditions

A facile synthesis of bromodifluoromethylated selenides under metal-free conditions is described here. Commercially available Me3SiCF2Br and bench-stable selenosulfonates react smoothly to give a broad scope of alkyl- and aryl-substituted bromodifluoromethylated selenides in moderate to good yields via a difluorocarbene intermediate. This protocol features a short reaction time, the absence of toxic waste, good scalability, and successful late-stage modification of bioactive molecules. In addition, the title products can be easily converted to different fluorinated and F-18-labeled selenides.

Automated summary

A facile method for synthesizing bromodifluoromethylated selenides under metal-free conditions has been described, with short reaction time, absence of toxic waste, good scalability, and successful late-stage modification of bioactive molecules. The resulting products can be easily converted to different fluorinated and F-18-labeled selenides.