An efficient Pd-catalysed Sonogashira coupling reaction was achieved in the absence of copper and amine with inorganic base using phosphene-free, air stable di(1𝐻-benzo[𝑑][1,2,3]triazol-1-yl)methane as ligand. The cross coupling of electron-rich, electron-defficient and hindered aryl halides with terminal alkynes afforded the internal alkynes in good to excellent yields.

An efficient strategy for the synthesis of α,β-unsaturated enaminones by the nucleophilic addition of N-heterocycles such as indole and imidazoles onto electronically bias alkynones under mild reaction conditions is described. Key feature of this reaction is the chemoselective addition of N-heterocycles onto ynones without affecting the 1^° amino groups (aromatic and aliphatic) of 5-aminoindole and tryptamine. The stereochemistry of the products was controlled by the tuning of reaction time. The mechanism of the reaction involves the Michael type addition of N-heterocycles on ynones via allene formation.