New group 14 5-metallated pyrrole-2-carbaldehydes 5-R3E(C4H2NR')CHO (E - Si, Ge, Sn; R = Mc, El, (n)Bu; R' = H, Me) have been regiospecifically prepared from corresponding pyrrole-2-carbaldehydes by either (i) 5-lithiation after protection of the aldehyde function by treatment with lithium N-methylpiperazide or by formation of an azafulvene dimer or (ii) metallation by R3EX (X = Cl, Br). The 5-silylated compound (E = Si, R = R' = Me) has been also obtained from 1-methyl-2,5-bis(trimethylsilyl)pyrrole.