Reactions of (chlorodifluoromethyl)benzene and (chlorodifluoromethoxy)benzene with nucleophilic reagents

Condensation reactions of (chlorodifluoromethyl)benzene and (chlorodifluoromethoxy)benzene with phenoxide and thiophenoxide ions have been performed in DMF or NMP with heating. In these conditions, the reaction between phenylselenide ion and (chlorodifluoromethyl)benzene did not occur. This latter reaction requires an additional visible light irradiation to proceed, as reported by Yoshida et al.