Enolates derived from α-(ortho-haloaryl)-substituted ketones undergo palladium-catalysed C– O bond formation to deliver benzofuran products in good yield. A catalyst generated from Pd2 (dba) 3 and the ligand DPEphos effects the key bond formation to deliver a variety of substituted products from both cyclic and acyclic precursors. The analogous thio-ketones undergo C–S bond formation using identical reaction conditions and are converted to ...