Facile and efficient diastereoselective synthesis of trans-indolyldihydrofurans by three-component reaction of 3-cyanoacetyl indoles with various aromatic aldehydes and N-phenacylpyridinium bromides in presence of 1,1,3,3-N,N,N',N'- tetramethylguanidine under solvent-free conditions is described. This ecofriendly protocol offers several advantages such as a cost-effective procedure with excellent yield, short reaction time, ease workup and product isolation, good functional group tolerance, and broad scope of usable substrates. The synthesized compounds were also evaluated for their antioxidant activity by 1,1-diphenyl-2-picrylhydrazyl radical scavenging assay.