Electrosynthesis of ethyl α,α-difluoro-α-(phenylseleno)acetate and its photochemical synthetic application

Anodic fluorination of ethyl α-fluoro-α-(phenylseleno)acetate was successfully carried out to give ethyl α,α-difluoro-α-(phenylseleno)acetate in high yield. Photolysis of the difluorinated product in the presence of various olefins provided regioselective difluorometylene adducts in good to moderate total yields. The reaction involves phenylselenyl transfer at the early stage followed by the elimination of a phenylselenyl group from the adducts once formed to provide the unsaturated and saturated difluoromethylene products.