Bilateral Aromatic Extension of Corannulene Nucleus

Abstract

Herein we show that a dibromo imide derivative of corannulene could be subjected to a palladium‐catalyzed Heck reaction in order to install aryl vinylene groups in a bilateral fashion on the C5‐symmetric aromatic nucleus. A photochemically‐induced oxidative cyclization then affords π‐extended structures in isolated overall yields of 35–44 %. Due to the aromatic area extension and the presence of electron withdrawing groups, the synthesized molecules exhibit an anodic shift of ≈1 V in their first reduction potential as compared to pristine corannulene. The bilateral growth of the aromatic scaffold, therefore, represents a viable strategy to prepare π‐extended corannulenes with an electron deficient character.