Stereoselective Synthesis of 3-(1,3-Diarylallylidene)oxindoles via a Palladium-Catalyzed Tandem Reaction.

We have developed an efficient three-component tandem reaction for the synthesis of 3-(1,3-diarylallylidene)oxindoles combining three palladium-catalyzed reactions: the Sonogashira, Heck, and Suzuki-Miyaura reactions. This method allows a stereoselective approach to each (E)- and (Z)-isomer by ligand change and controlling the reaction temperature.

Palladium-Catalyzed One-Pot Approach to 3-(Diarylmethylene)oxindoles from Propiolamidoaryl Triflate.

3-(Diarylmethylene)oxindoles have been synthesized from propiolamidoaryl triflate utilizing a palladium-catalyzed one-pot reaction consisting of three successive reactions: Sonogashira, Heck, and Suzuki-Miyaura. This method allows for the production of a complex skeleton of 3-(diarylmethylene)oxindole from propiolamidoaryl triflate using a commercially available aryl iodide and arylboronic acid in a simple and efficient way with moderate yield and stereoselectivity.