Non-Directed Pd-Catalyzed Electrooxidative Olefination of Arenes

The Fujiwara-Moritani reaction is a powerful tool for the olefination of arenes by Pd-catalyzed C–H activation. However, the need for superstoichiometric amounts of toxic chemical oxidants makes the reaction unattractive from an environmental and atom-economical view. Herein, we report the first non-directed and regioselective olefination of simple arenes via an electrooxidative Fujiwara-Moritani reaction. The versatility of this operator-friendly approach was demonstrated by a broad substrate scope that includes arenes, heteroarenes and a variety of olefins. Electroanalytic studies suggest the involvement of a Pd(II)/Pd(IV) catalytic cycle via a Pd(III) intermediate.