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 C(60). Recently, even fluoroarenes were subjected under relatively mild conditions to intramolecular C(Ar)-C(Ar) couplings by combining the cleavage of C(Ar)-F with the formation of very strong Si-F or Al-F bonds (see picture; green C, white H).
Laboratorium für Organische Chemie, ETH Zürich, Wolfgang-Pauli-Strasse 10, 8093 Zürich, Switzerland. thilgen@org.chem.ethz.ch
Carlo
C
Thilgen