Cyclopentadiene and metallocenes, typically zirconocene dichloride, are suitable substrates for multiple arylations with aryl bromides in palladium-catalyzed reactions. Thus, various aryl bromides bearing either an electron-donating or an electron-withdrawing substituent can react with these substrates to afford the corresponding 1,2,3,4,5-pentaaryl-1,3-cyclopentadienes in a single preparative step. Derivatives of cyclopentadiene, including di- and trisubstituted cyclopentadienes, and indene are arylated in a similar fashion.