One-pot Pd/C catalysed 'domino' HALEX and Sonogashira reactions: a ligand- and Cu-free alternative

The advantages of combining heterogeneous catalysis and aryl chloride substrates for cross-coupling are introduced. A heterogeneous Pd/C catalyst is used for activating aryl bromides and electron withdrawing aryl chlorides via a one-pot 'domino' HALEX-Sonogashira reaction. No ligand or co-catalyst is required, and the cross-coupling products are obtained in moderate to good yields. The influence of the solvent, base, iodide source and catalyst is evaluated. The catalyst is reusable for at least six consecutive reaction cycles. A variation on this reaction using catalytic amounts of KI is also proposed.