Amphiphilic Dendrimer as Reverse Micelle: Synthesis, Characterization and Application as Homogeneous Organocatalyst

Abstract

The core and surface terminal groups are the two main catalytic sites in a dendrimer. In most of the reported examples, the catalytic sites in dendritic catalysis are the surface terminal functional groups. This perspective article concerned with the dendrimer based catalysis, involving these two catalytic sites and the dendrimer cavities. The interior cavities provide the nanoscale reactor sites, by creating reverse micelle like appearance for catalysis. In exploring the significant achievements in this area, a low generation PAMAM dendrimer with amphiphilic nature, having a polymeric core with large number of pendent amino groups was synthesized and concentrated its catalytic activity. The key features with respect to positive and/or negative catalytic activity was highlighted by synthesizing various aryl and heteroaryl 2-substituted benzimidazoles. The synthesized dendritic organocatalyst was proved to be amazingly reactive and gave high yield of products within a few minutes at room temperature with low catalyst loading. Here, a new stable hemiaminal, the species rarely been detected and much less isolated in bulk, was obtained during the synthesis of benzimidazoles. Moreover, this is the first reported method for the synthesis of benzimidazoles, using the homogeneous PAMAM dendrimer as a basic organocatalyst.