·YlideFluor-CF2Cl: a shelf-stable, versatile electrophilic or radical chlorodifluoromethylating reagent

Abstract

An easily available chlorodifluoromethylating reagent YlideFluor-CF₂Cl based on the sulfonium ylide skeleton was developed. Under blue light irradiation, YlideFluor-CF₂Cl underwent homolytic S–C bond cleavage to generate ClCF₂˙, which reacted with electron-rich alkenes or heteroarenes to afford the corresponding chlorodifluoromethylated products. Alternatively, YlideFluor-CF₂Cl may act as an electrophilic chlorodifluoromethylating reagent to react directly with soft carbon nucleophiles derived from β-ketoesters to give the chlorodifluoromethylated compounds in good yields.