Expanding the family of indenocorannulenes

ORGN 757

Brian D. Steinberg, steinbbr@bc.edu and Lawrence T. Scott, lawrence.scott@bc.edu. Department of Chemistry, Boston College, Merkert Chemistry Center, 2609 Beacon Street, Chestnut Hill, MA 02467-3860
The construction of large curved aromatic π systems continues to be a challenge in organic synthesis. Our work highlights how a halogenated corannulene core can be reacted in two simple steps to access curved aromatic molecules. A Suzuki-Miyaura coupling, followed by Flash Vacuum Pyrolysis, provides mono-, di-, tri- and tetra-indenocorannulenes (shown below). The synthesis of tetraindenocorannulene, while novel on its own merit, represents an approach which can easily transform corannulene into an advanced synthon for larger curved aromatic systems.