[2-(N,N-Dialkylamino)ethy]cyclopentadienes have been used for the synthesis of the novel amino-functionalized silicon- and carbon-bridged cyclopentadiene derivatives 3a-c, 7, 10 and 13a-c. The C-C and C-Si coupling reactions described here are regioselective leading exclusively to the formation of 1,3-disubstituted isomers, as proven by H-1 NMR spectroscopy. The bis-cyclopentadienes 3a-c, 7, 10 and 13a-c can be deprotonated to the corresponding dianionic species.