Pd-catalyzed imine-directed one-pot access to polysubstituted pyrroles via tandem triple isocyanide insertion/aza-Nazarov cyclization reactions

Herein, we report a novel one-pot method for synthesizing polysubstituted pyrrole derivatives via three-component reactions of alkenyl bromides, amines, and isocyanides. The conversion process is catalyzed by a Pd catalyst without additional ligands. The key feature of this methodology is the orderly insertion of three isocyanide molecules which is directed by the intramolecular imine group. The method also provides an alternative way to synthesize cyano compounds from isocyanides. DFT calculation results support part of the proposed reaction mechanism.

Automated summary

Herein, we describe a novel one-pot method for the synthesis of polysubstituted pyrrole derivatives via a three-component reaction of alkenyl bromides, amines, and isocyanides. The conversion process is catalyzed by a Pd catalyst without the need for additional ligands. The key feature of this method is the orderly insertion of three isocyanide molecules, directed by the intramolecular imine group. Additionally, DFT calculations provide support for the proposed reaction mechanism.