Intramolecular aryl-aryl coupling of fluoroarenes through Al2O3-mediated HF elimination

A strategy for effective intramolecular aryl-aryl coupling of fluoroarenes through Al(2)O(3)-mediated HF elimination is reported. It is demonstrated that the C-F bond, which is widely believed to be the most passive functionality in organic chemistry, can be reconsidered as a useful functional group allowing very effective C-C bond formation. The solid-state strategy presented in this study opens the possibility for facile syntheses of insoluble extended polycyclic aromatic hydrocarbons.