Sterically hindered 2,5-diphenyl-and 2,3,5-triphenyl-1-vinylpyrroles have been obtained by the vinylation of the corresponding NH-pyrroles with acetylene in superbasic catalytic system KOH—DMSO in up to 78% yield. 2,3,5-Triphenyl-1-vinylpyrrole has also been obtained in 75% yield by the regioselective bromination of 2,3-diphenyl-1-vinylpyrrole with subsequent cross-coupling of 5-bromo-2,3-diphenyl-1-vinylpyrrole with phenylmagnesium bromide in the presence of dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium(II). 2,5-Diphenyl- and 2,3,5-triphenyl-1-vinylpyrroles undergo a free-radical polymerization (AIBN, 80 °C) to form oligomers in 11 and 27% yield, respectively.