Redox-ligand sustains controlled generation of CF3 radicals by well-defined copper complex

Abstract

A well-defined copper complex bearing iminosemiquinone ligands performs single electron reduction of an electrophilic CF₃⁺ source into CF^˙₃ radicals. This redox behavior is enabled by the ligand which shuttles through two different redox states (iminosemiquinone and iminobenzoquinone) while the copper center is preserved as a Cu(II). This system was used in the trifluoromethylation of silyl enol ethers, heteroaromatics and in the hydrotrifluoromethylation of alkynes. This is the first example of cooperative redox catalysis for the controlled generation of CF^˙₃ radicals.