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Synthesis of Cyclopenta‐HBCs and their Regioselective Chlorination During Oxidative Cyclodehydrogenation |
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| Authors: | Thomas B J Hall Bryce R Hoggard Christopher B Larsen Nigel T Lucas |
| Abstract: | Hexa‐peri‐hexabenzocoronenes with a bay‐fused five‐membered ring are synthesized from fluorenyl precursors. The key oxidative cyclodehydrogenation step is accompanied by regioselective chlorination that is enhanced by methylation at the cyclopenta‐ring or increased reaction concentration. The CpHBC products undergo mild electrophilic aromatic bromination, without catalyst, to afford adducts suitable for π‐extension by cross‐coupling. |
| Keywords: | annulation aromatic substitution fused-ring systems hexabenzocoronene oxidative cyclodehydrogenation |