Binaphthyl-Stabilized Palladium Nanoparticle-Catalyzed Stereoselective Synthesis of 3-Arylidene-2-oxindoles via One-Pot Heck-like Carbocyclization/Nucleophilic Addition

Stereoselective, one-pot synthesis of 3-arylidene-2oxindoles has been accomplished via Heck-like carbocyclization/ nucleophilic addition of N-(2-iodophenyl)-N-methyl-3-phenylpropiolamide, phenylacetylene, and secondary amine using binaphthyl stabilized palladium nanoparticles (Pd-BNP) as a reusable catalyst. Less reactive aryl bromides generally provided a similar yield of 3-arylidene-2-oxindoles compared with more reactive aryl iodides. The Pd-BNP nanocatalyst has been recovered and recycled for five catalytic cycles with only an insignificant reduction in particle size, reactivity, and reaction yield.

Automated summary

Stereoselective, one-pot synthesis of 3-arylidene-2oxindoles has been achieved using binaphthyl stabilized palladium nanoparticles (Pd-BNP) as reusable catalyst. The synthesis involves Heck-like carbocyclization/ nucleophilic addition of N-(2-iodophenyl)-N-methyl-3-phenylpropiolamide, phenylacetylene, and secondary amine. The Pd-BNP nanocatalyst can be recovered and recycled for multiple catalytic cycles with negligible reduction in particle size, reactivity, and reaction yield.