Preparation and reactions of 2-chloroperfluorocycloalkenylcopper reagents

Abstract

1-Chloro-2-iodoperfluorocycloalkenes react with activated zinc powder in dimethylformamide solvent at room temperature to give 2-chloroperfluorocycloalkenylzinc reagents. Treatment of these organozinc reagents with copper(I) bromide at 0 °C or at room temperature provides a simple route to the corresponding 2-chloroperfluorocycloalkenylcopper. The yield is excellent. These organocopper reagents, which are stable at room temperature in the absence of oxygen and/or moisture, can be used for the production of C–C bonds via reactions with alkyl, aryl and acyl halides. Reaction of these organocopper reagents with acyl halides leads to previously unreported acylated polyfluorocycloalkenes.