Sonogashira reaction catalyzed by palladium isocyanide complex modified in situ

Palladium isocyanide complex modified in situ by addition of benzohydrazide as nucleophile was shown to catalyze Sonogashira reactions of phenylacetylene with iodobenzenes in refluxing ethanol in the presence of potassium carbonate. The reactions were complete in 2 h, and neither preliminary degassing nor protection from atmospheric moisture and oxygen was necessary. The yields of the cross-coupling products, unsymmetrical diarylacetylenes were only slightly lower than those obtained with the preliminarily prepared catalyst. The proposed procedure was used to synthesize a series of diarylacetylenes containing both electrondonating and electron-withdrawing substituents in the benzene rings.