Pd/C-catalyzed aerobic oxidative C-H alkenylation of arenes in γ-valerolactone (GVL)

A novel methodology for the heterogeneous palladium-catalyzed C-H alkenylation of N-methoxybenzamides and anilides is presented. This approach is based on the use of commercially available Pd/C as catalyst and molecular oxygen as terminal oxidant, in combination with a substoichiometric amount of benzoquinone. Furthermore, the reaction can be conducted in non-toxic biomass-derived gamma-valerolactone (GVL) as reaction medium. The catalytic system exploited high activity leading to good isolated yields to several interesting products. In addition, the catalyst showed a remarkable stability in the reaction conditions, allowing its recycling in consecutive reaction runs.