Generation of indole ring systems based on cyclisation of 2-alkynylaniline moieties on solid supports have been investigated. The cyclisation reactions were studied in 3 different conditions: (i) iodonium-mediated cyclisation (iodo-cyclisation) (ii) base-promoted cyclisation, and (iii) palladium (II)-mediated cyclisation. Only the latter with palladium dichloride gave satisfactory results on polystyrene resin solid supports.