Palladium-immobilized triazine dendrimer on magnetic nanoparticles: as reusable microreactor for solvent-dependent synthesis strategy of 2,3-diphenylindoles and pentaphenylpyrrole derivatives

In this work, we demonstrate that palladium-immobilized triazine dendrimer on magnetic nanoparticles in proper solvents, provides an impressive, atom-economical and compelling approach for the selective synthesis of 2,3-diphenylindole or pentaphenylpyrrole derivatives via annulation of diphenylacetylene with diverse anilines. Both the annulation methods were taken place under copper- and phosphine-free conditions with high yields at air atmosphere. Likewise, bis-indoles were obtained with excellent yields under optimized reaction conditions. Besides, the catalyst was isolated and reused for seven cycles without decrease potential of catalytic activity. Two mechanistic pathways were proposed and geometry optimizations, electronic properties as well as vibrational characterizations of all structures were performed with density functional theory (DFT). Also, the investigation of atomic basin properties of these molecular systems was carried out utilizing the quantum atoms-in-molecules theory (QTAIM). The results showed that 2,3-diphenylindole and pentaphenyl pyrrole molecular systems can be used as intramolecular acceptor/donor (n-like/p-like) sections.