Synthesis of C3 Benzo[1,2-e:3,4-e’:5,6-e”]tribenzo[l]acephenanthrylenes (“Crushed Fullerene” Derivatives) by Intramolecular Palladium-Catalyzed Arylation

The C₆₀ polyarenes 4, 5, 18a, and 18b have been synthesized from truxene by triple alkylation at C5, C10, and C15 followed by a palladium-catalyzed intramolecular arylation. The synthesis of crushed fullerene C₆₀H₃₀ (2) is the most efficient reported to date and proceeds in 33% overall yield.