Bilateral Aromatic Extension of Corannulene Nucleus

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 struct...

Full description

Saved in:
Bibliographic Details
Published in:European journal of organic chemistry 2022-05, Vol.2022 (18), p.n/a
Main Authors: Halilovic, Dzeneta, Csókás, Dániel, Webster, Richard D., Stuparu, Mihaiela C.
Format: Article
Language:English
Subjects:
Chemical synthesis
Corannulene
Electron-deficient compounds
Fused-ring systems
Palladium
Photochemistry
Polycyclic aromatic hydrocarbons
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary: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. This work explores bilateral aromatic extension of the corannulene nucleus through a combination of Heck and Mallory reactions.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.202101548