Selectivity studies in the reaction between iodobenzene and phenylacetylene: Sonogashira coupling vs hydroarylation

Abstract The selectivity of the coupling reaction between iodobenzene and phenylacetylene was evaluated. Several palladium catalysts, ligands and reaction conditions were tested, showing that supported catalysts, room temperature or ionic liquids (NHC precursors) favor Sonogashira coupling, while the non‐supported ones, higher temperature and PPh3 as ligand, favor hydroarylation. Neither excess of iodobenzene nor phenylboronic acids are required; and it is possible to avoid the use of PPh3, although this lowers selectivity. Copyright © 2008 John Wiley & Sons, Ltd.