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

Abstract

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 18F-labeled selenides.

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