Direct Oxidation of Aryl Malononitriles Enabling a Copper-Catalyzed Intermolecular Alkene Carbochlorination

A copper-catalyzed carbochlorination
of alkenes with aryl malononitriles
and chloride is disclosed. This net oxidative transformation proceeds
with activated and unactivated alkenes with moderate to excellent
yields. Mechanism experiments suggest addition of the malononitrile
radical to form a secondary carbon radical which is intercepted by
a chloride source. The resultant products can be transformed into
biologically important γ-lactones in one further step.