Palladium-catalyzed intramolecular rearrangement of vinylidenecyclopropanes through C–C bond activation

Abstract

Vinylidenecyclopropanes bearing sulfonamide can undergo a novel intramolecular rearrangement to give the corresponding functionalized dimethylenecyclopropanes in moderate to good yields in the presence of Pd(OAc)₂ in toluene upon heating through C–C bond activation based on weak coordination of the sulfonamide directing group. The reaction pathway can be changed for phenyl substituted vinylidenecyclopropane, giving another type of dimethylenecyclopropane in methanol in the presence of K₂CO₃ under reflux.