Radical conjugate addition of ambiphilic fluorinated free radicals

The ambiphilic character of fluorinated radicals was noticed during their radical conjugate addition onto electron-deficient alkenes. Free radicals were trapped with enones when the reaction was conducted from iododifluoro-acetate and -phosphonate derivatives in the presence of Et3B. Competitive addition reaction onto electron-rich or -deficient alkenes was observed depending on the free radical initiator.