The approach of exploiting sterically demanding and electron donating groups to force high degrees of silylation allows the isolation of sterically overcrowded cyclopentadienyl compounds in multigram scale. Even a subsequent methylation to obtain the trimethylsilyl substituted analogues should be feasible to obtain a chemically more inert and increasingly overloaded compounds. In the future, the syntheses of other main group, transition metal or lanthanide or actinide complexes with persilylated cyclopentadienyl ligands could be of great interest.