Synthesis of Geodesic Polynuclear Arenes and Fullerenes by Intramolecular Aryl–Aryl Coupling

Bending over backwards to build buckybowls and -balls? For the last two decades, flash vacuum pyrolysis of chloro- and bromoarenes has been the method of choice for intramolecular aryl–aryl couplings that afford geodesic polynuclear arenes (“buckybowls”) including fullerene C₆₀. Recently, even fluoroarenes were subjected under relatively mild conditions to intramolecular C_ArC_Ar couplings by combining the cleavage of C_ArF with the formation of very strong SiF or AlF bonds (see picture; green C, white H).