Palladium-Catalyzed Skeletal Rearrangement of Cyclobutanones via C–H and C–C Bond Cleavage

The palladium-catalyzed skeletal rearrangement of 3-arylcyclobutanones into 1-indanones is reported. A Pd(0)/IMes catalyst allows for the cleavage of C(carbonyl)–C(sp3) and C(sp2)–H bonds to result in the skeletal rearrangement, and neither an extra reactive functional group nor a directing group is required to promote the reaction. Deuterium-labeling experiments indicate that the C–C bond is initially activated and that the subsequent C–H activation is involved in the rate-determining step.