A convenient synthesis of amides and nitriles with a branched and conjugated dienyne structure

An efficient and stereoselective synthetic approach to a variety of amides and nitriles with a branched and conjugated dienyne structure has been developed, starting from a readily available mono-silylated unsaturated amide and nitrile with an enyne structure. A nucleophilic hydrohalogenation of the triple bond of the enynes with NaI afforded a Z,E-iododienamide and a Z,E-iododienenitrile that, subjected to palladium-catalyzed cross-coupling reactions with a variety of terminal alkynes, led directly to the title compounds.